We continued to keep our journals after the forty days were finished. The following excerpts reveal what happened between us over the months that followed—what we were feeling, how confused we were, how complicated things became, how we decided to do the blog, and the incredible outpouring of fans and media attention in response to it.
April 29, 2013: It was the first day after Day 40. I was heading home from work when I received this email from Tim. I called him to talk about it. He sounded depressed. He said he had been staring at his computer screen most of the day in his apartment, trying to work, but he was unable to concentrate or get anything done. He said he felt empty, like he had lost something.
I had some time today to think about what has happened over the past few days. I am not entirely sure Tim was really ready to end things between us. I think he cares about me more than he is letting on. Even on our plane ride home, he said he wanted to keep dating, but he really feared screwing things up further. He repeatedly asked me “why” I liked him so much, as if doubting his own self-worth. It’s hard to tell what was going through his head, or why he kissed me last night as if he wasn’t ready to let go.
I am also not entirely sure he fully understands why he wanted to end things. Maybe it’s because we were wrong for each other. Or maybe he was pushing me away to see if I’d fight back. Maybe he is insecure, and by default my interest in him makes him think he can do better. Or perhaps he does just love the chase and wasn’t satisfied that I wouldn’t give it to him. Maybe it’s a combination of all these things. Whatever it is, I wish he could be more decisive.
April 31, 2013: Tim asked how I was holding up. Usually I feel so down when a relationship fails. I was feeling depressed in Disney World and on the plane ride home. However, since I’ve been back I’ve felt an overwhelming sense of relief and freedom. At the same time, hearing Tim’s sadness on the phone the other day, but not feeling the same way myself, has brought tremendous feelings of guilt. Shouldn’t I feel grief? I told my friend about my confusion. She said getting out of a bad relationship is like having a wisdom tooth pulled: You don’t realize how bad it was until it’s gone. My mom always said you should never chase affection; people usually show you what they’re willing to give rather quickly and if it’s not given freely, it’s not worth having.
I’ve had this insight: I was so caught up in trying to make things work between us that I was blinded by how the relationship was failing me. Tim would never really let me in emotionally in a deep and trusting way, and I want that kind of intimacy with a partner. No matter how close we became, there was always a wall up around him, as if he couldn’t fully trust himself, or me. On the plane when we talked about our decision to end things, and he was wavering on what to do, I assured him if he did really like me, there wouldn’t even be a need for a decision. That this shouldn’t be so difficult. I told him that when you know it’s right, you just know. Truthfully, though, I don’t know. Maybe we could have had a chance if he had let us. Maybe we could have had a chance if I had fought for him. But I have to question why I didn’t. I guess I was just tired of his uncertainty and negativity and knew deep down that the absence of emotional intimacy would always be a problem. I guess in part I was also looking for a way out.
May 2, 2013: Sometimes it scares me how my emotions and moods can waver. Earlier this week I journaled about how I felt such a huge sense of relief now that the experiment, our relationship, was over. I’ve felt confident and relieved to be single. Yet now, only a few days later, I am lonely. It’s a Friday night and most of my friends are out of town. My sister is busy and I find myself bored, restless, and wondering what’s next. After a glass of wine, I had a moment of weakness. I went online and reactivated my OkCupid account. I was immediately bombarded with dozens of messages and requests, but I didn’t respond to anyone; I’m not ready to date. I guess I just needed a little ego boost, pathetic as it sounds. How can I go from complete confidence one day to falling into a hole of insecurity the next?
May 3, 2013: I miss hanging out with Tim as a friend. I hope we can get back to how things were before the experiment. I texted him to let him know:
After his sad call the other day, I can’t tell what this means. “I miss hanging out with you” and “I miss you” are two different things. I am probably reading too much into it, but I want to be careful not to mislead him. It goes back to the age-old question: Can men and women just be friends? We were friends before, but we were still, in some ways, always curious about each other. We’ve talked before about whether this experiment was a way to date each other without the usual risks. In a way, the experiment provided some sort of protection for us: It had a built-in expiration date. It was supposed to end. Anyways, I hope we can go back to being friends.
May 4, 2013: I went to Los Angeles for the weekend. I made dinner plans with my friend Nicole and her wife, Noreen. They met last year, fell in love instantly, were engaged within a few days, and got married after a few weeks. Their story is a reminder of how quickly life can change. It also makes me excited that my future in this arena is wide open and unknown. I told them about my history of failed relationships this past year, and now this crazy experiment with Tim.
Noreen told me I am probably going after the wrong guys. She said she had been searching for the right partner for years with no luck. Finally, a friend gave her a book, which said that in order to find the right person, you need to have complete clarity and focus on who you are looking for. It suggests making a list of all the qualities you are looking for in a partner and to remind yourself of the list often. So Noreen wrote her list on a chalkboard wall in her bathroom and stared at it for days. Two weeks later, she met Nicole, who embodied everything she was looking for. I’m not sure I believe all this, but it can’t hurt! So I made my list:
May 7, 2013: This week Tim and I had planned to have a final therapy session with our therapist, Jocelyn. The idea was to review everything that had happened during the experiment and talk about what we were feeling now and what we have learned. The problem is, I have a bad feeling about it. I worry that if Tim wasn’t ready to end things, he might use this as an opportunity to try to start things up again. Which would be fine, if he is 100 percent sure and confident about wanting to date me, but if that’s the case he should man up and just say it. He shouldn’t need a couples therapist to gain the courage for that.
May 9, 2013: Tim came by my studio this morning. We had planned to go through the journal entries we’d kept during the 40 Days experiment. As we were reading through our first few entries, side by side, we were shocked at how differently we interpreted the same experiences. We found the male/ female perspective to be fascinating. We knew that our relationship issues were universal and we thought people might relate to our struggles and failures, and through our story they might be inspired to seek out answers for themselves. So we talked about the idea of sharing our journal entries with the public and made the final decision to post the entries online via a blog. It will be a lot of work putting it all together, but we think it will be worth it.
As I was reading through his entries, Tim walked up behind me and grabbed me around the waist. He drew me in, hugged me tightly, and kissed me a few times softly on the side of my head. He held me like this for a minute in silence. I froze as I sorted through my feelings. What was he was doing? What was I doing? Did he want to be friends with benefits? Did he want to be with me again? I pulled away and asked him what was going on. He said he’d been wondering what it would be like if we could date without all the rules, outside of the context of the experiment. That he was afraid he had made a mistake. But he also told me that the experiment had happened so fast, and he didn’t have enough perspective yet on it to know his mind completely. He said he was confused.
The uncertainty was the perfect reminder of everything that was wrong between us romantically. I don’t want to date Tim again if he’s still confused and emotionally detached. It’s not attractive to me. I want a man who is sure of himself and of what he wants, appreciates me, and is proud to have me by his side. I told Tim he was being unfair and he should make up his mind about what he wants before getting involved again. That if he was really serious and sure about dating me, we could talk, but otherwise we should just focus on rebuilding our friendship.
May 12, 2013: After much thought, I decided to stop going to my own therapist, who I’ve been seeing for almost a year now. When I started seeing him, I had developed all this anxiety about keeping up appearances and expectations, and about maintaining a certain level of achievement. Suddenly the work that once brought me joy was attached to fears. I realize now how ridiculous that mind-set was. I was putting way too much pressure on myself and causing so much unnecessary stress. No wonder I was jumping into relationships so quickly: I was looking for a distraction, anything to replace the enjoyment and love I used to get out of my work. Of course those relationships failed!
After this “boot camp” of self-reflection, along with the experiment with Tim, I feel like I am in a really great place. I’ve learned to let go, just be me, and go easier on myself. I’ve regained joy in my work and stopped caring about perceived expectations. The world doesn’t end when I forget to respond to a work-related email. The world doesn’t end if I take a weekend or two off or say “no” to meetings or hanging out with friends.
The other day, Tim and I were discussing how interesting it is that the experiment started out as an attempt to solve relationship issues, but how it really helped us on other personal levels. The conversation reminded me that despite the drama around the project, our friendship is special. Many people only want to talk about the superficial stuff, but I can have deeper conversations with him about life and never feel any judgment.
May 13, 2013: I went to Berlin with my sister on a business trip. After the conference was over we went to a nightclub called Berghain. Over the past few months, she’s been introducing me to techno and house music, and a few DJs she likes were there that night. I am not much of a party girl by nature. I am a homebody who would prefer to spend my Friday night in pajamas doing work or watching a TV series with a glass of wine. I’m glad she was there to pull me out of myself. When else in my life would I be dancing all night long in a dirty old warehouse space in Berlin? I had one of the most incredible nights of my life, full of perfect moments that I will never forget. We lost ourselves in the music. All insecurities went out the door. It made me appreciate being young, being single, and having the freedom to have these experiences that may not be so appropriate one day. At sunrise, they rolled the windows up in the warehouse, where we were all still dancing. My sister and I hugged and talked about how much we loved each other.
May 18, 2013: I hadn’t looked at OkCupid in the weeks since that lonely night when I reactivated my account. However, a friend suggested I start dating casually. It can’t hurt to have a little fun. So I set up a date with a guy to meet at the Bourgeois Pig in the East Village for wine.
On paper he looked pretty awesome, and it sounded like we had a lot in common. It was a disaster! We barely had anything to say to each other. I paid after one drink, politely left, and met some friends at another bar where we laughed about it.
May 25, 2013: I had a date tonight with Zak, a guy I met on OkCupid recently. We met at a little bar in Williamsburg called Post Office. I couldn’t believe how easy and natural conversation was between us. He has a very laid-back and easygoing personality. He made me feel instantly comfortable and didn’t stop making me laugh. We were able to talk about so many topics, and it felt like we related on many levels. He is a cinematographer and seems to genuinely love his work. To top it all off, I am very attracted to him. The night passed quickly, and I left around 11:00 P.M. to meet up with some friends for a birthday party. After a few other disastrous dates this week, it was nice to finally have one good one!
June 5, 2013: Tim is experiencing a lot anxiety about all the work we have to do to launch the 40 Days blog. He was driving himself a little crazy over it, so I tried to give him advice and take some of the load off his plate. That backfired: He said I was being too motherly but also that I was too accommodating. After a long string of misunderstandings and an angry phone call, I ended up getting a little worked up myself. I just don’t understand our communication breakdowns. We never used to fight like this before we dated. Anyway, he wrote me a nice email, and we both apologized about it in the morning.
June 10, 2013: Tim and I have been going over the details of launching our diary entries on the website. It’s been a little stressful creating the website with him. I talked to a friend about it. She observed that it’s funny how Tim and I have fairly stereotypical gender-specific issues in relationships, but when it comes to other aspects of life, like my work, my personality is much more typical of a man. I can be very direct about what I want, I’m less emotional, and I talk about issues head-on. Tim, on the other hand, can be very sensitive to my criticism and indirect about what he wants. He keeps things that bother him to himself and lets them fester until he’s so frustrated that they suddenly boil up and he gets angry with me.
Meanwhile, I’ve been texting and emailing a lot with Zak. Our conversations have been lighthearted and funny, and they’re a nice distraction from all the drama with Tim. Zak is pretty persistent about keeping up the conversation, and keeps texting that he wants to hang out again soon. I want to see him again, but I’m purposefully trying to slow things down. I don’t know if I am ready for something serious again.
June 15, 2013: I was telling Tim about this care package I received in the mail from some guy I’ve never met. The guy found out my favorite foods from my Facebook profile and sent me a big box of avocados, chocolate, and coffee. There was also a USB stick with a presentation he designed that contained mood boards of options for our first date. It was quite involved, made me feel obligated to say yes to a date with him. But I canceled when I found out I was going to Barcelona for work. He then proposed we meet up in London, while I was over there. Here I was thinking that I moved fast! I told Tim about it:
Tim and I decided to meet up later at a cocktail party. I got pretty tipsy, and I was wearing five-inch high heels, and at one point in the night one of my heels broke off. We were laughing at my waddling around this very fancy venue like a penguin. At the end of the night Tim had to practically carry me out of the party. We shared a cab home and were having a great time. I still care for him deeply. There was a moment when I wanted to kiss him, but I held back. I was drunk, and I knew I’d regret it later. We’re not right for each other, and I don’t want to complicate things more than they already are.
June 18, 2013: A few days ago I met up with Zak for a second time; we had a brief lunch date. Last night we continued the conversation at a bar in Williamsburg. His honesty and forwardness with intimate and emotional details about his personal life were refreshing. I felt like I could pretty much tell him anything without any judgment. He seems at peace with himself and with life, and he has such a great energy. There doesn’t seem to be any sort of “front” or “facade” with him—he wears his heart on his sleeve and is confident about it. The most striking thing about him is how relaxed and calm he is. We talked about how much we both hate drama. I slept over at his place. This morning we went to breakfast at a cute little place called House of Small Wonder and were talking about how we were overdue for a trip to the beach. He told me about this beautiful spot in Mexico called Tulum that isn’t too touristy. Zak joked that we should just run off for the weekend, and I said, “Why not?” I was joking, but next thing I know, he pulls out his iPhone and buys the plane tickets. I love how spontaneous he is! Why is it that I meet an awesome guy when I’m not looking for one?
June 19, 2013: Parsa emailed me this note today. He’s the ex-boyfriend who broke my heart last December and left me completely confused about what went wrong. I blamed myself for everything. He made me question myself and how I approached relationships. It was part of what drove me into the dating experiment with Tim. Even though it’s been over six months, it was really nice to hear from him and get clarity on what went wrong. I finally feel like I have some closure on that relationship now. It also was a nice reminder that it is never too late for apologies. I probably owe a few to guys I may have unintentionally hurt in the past.
June 21, 2013: I received this email from Tim the other day:
Afterward we had another conversation on the phone. I asked him why he was changing his mind now. He said he felt like he had fucked up. He said he truly wants to try to date me again, but he sees now that he waited too long and now I’m gone. He said the idea of a relationship with me always scared him. He said for years he felt like I was “a girl you marry, not date,” and that this idea put too much pressure on him. He’s sure, now, that he wants to try dating me. I probably would have tried dating him again if he had told me this sooner and with more confidence. Life is all about timing, and it is not on his side. Zak, on the other hand, has let me in closer emotionally in only three dates in ways that Tim never did. There was always a barrier with Tim. This gives me more confidence that Tim and I were just not the right match. Even if we had tried dating again, I don’t think we would have lasted. I hope with all my heart that Tim finds someone he is completely comfortable with, who he can let his barrier down with. He deserves that.
June 30, 2013: I jetted off to the beautiful sandy beaches in Tulum, Mexico, with Zak this weekend. I didn’t tell Tim I was going, even though he kept asking me what I was doing during the weekend. I felt bad since he had told me he wanted to get back together. I didn’t want to hurt him by rubbing it in his face about Zak. The trip was truly magical. The landscape in Tulum was almost surreal. In the mornings we’d do yoga and hang out on the beach together. In the afternoons we drank cocktails, explored the Mayan ruins, and went cave diving in the cenotes. At night we stayed up for hours talking about all aspects of life. While we met only a month ago, he’s been very forward about his fondness for me. He told me how he never expected to meet someone like me. That he’s been searching for a long time, that he had almost given up.
July 4, 2013: For the Fourth of July I went to a dance party on a Brooklyn warehouse rooftop with Zak and my sister. We danced all day long until the sun set behind the Manhattan skyline. Later we sat by the waterfront in Brooklyn, listening to music and talking. Zak turned to me at one point and said, “One day, eventually, you’re going to get mad at me. I want you to remember how happy and how perfect everything is in this moment, and I hope you’ll find it in your heart to forgive me.” I can’t even imagine ever being mad at this guy. He is so perfect for me, and I’ve never been happier. I told Tim I was falling for Zak, and he did not seem very happy about it. He warned me to be careful and not let another situation like Parsa happen again. While I am aware that love makes me vulnerable, I don’t want to hold on to fear and let it run my life. I know Tim sees my ability to love people without much reservation as a weakness, but I believe he is mistaken. The vulnerability that love requires, the complete openness and trust—this is not something everyone can handle. You need strength to be vulnerable. I believe that running from it or putting up walls only makes you scared, not strong.
July 11, 2013: Tim and I launched our journal entries to the public a few days ago via our blog, www.fortydaysofdating.com. I have a bit of anxiety about it. I am pretty open and honest about my most intimate thoughts and feelings during that time. I wonder what my family, clients, or even work colleagues will think about it? And I worry about how Zak will react when he reads the intimate details about my relationship with Tim. I hang out and talk with Tim all the time, and I wonder if that will start to bother Zak once he reads about what happened between us. On another note, Tim continues to tell me about his dating escapades. He’s clearly frustrated with himself for falling back into his old patterns with women.
July 15, 2013: The response to our 40 Days blog has been crazy. We’ve had hundreds of emails from the press wanting to do interviews, and today we got our first emails from producers in Hollywood about turning the experiment into a movie. I am completely shocked. I never imagined our little dating story would go viral. The attention has been exciting but overwhelming. I feel like there aren’t enough hours in the day to respond to everyone.
July 23, 2013: I got this text from Tim:
The more I think about it, the more frustrated I become. I can’t figure out if he is just playing games or if he really believes this. I don’t know which is worse. If he’s making this up in one last attempt to get back with me, it’s not going to work. Even if he does believe he feels this way, what purpose does it serve now? He knows I’ve fallen for Zak, so what’s he doing? Is he trying to sabotage our friendship? Some things are better kept to yourself. I’ve always believed words are cheap and it’s a person’s actions that speak the loudest. Tim never did anything to show me these feelings, and I just don’t understand where this is coming from right now.
July 29, 2013: Lately it has become more and more difficult to work together with Tim. We have so much work to do on the artwork and videos for the blog, and this is on top of our regular work. Ever since launching the site, we’ve been bombarded with fan mail and interest from Hollywood. I am doing my best to do as much as I can, but it never seems to be enough for Tim. Maybe he’s frustrated that I didn’t reciprocate the “I love you” message. There have been angry texts, dozens of emails in the middle of the night, and frustrating phone calls between us. I told him that if we couldn’t work together professionally, I was going to have to quit the project. I won’t let a blog ruin my life or our friendship. He wrote back suggesting that we go to therapy again. As crazy as it sounds, I am willing to try anything if it makes things right between us. We made an appointment for a few weeks later.
August 3, 2013: Things are more strained with Tim. There is so much pressure between my work and the blog and finding time for Zak, and Tim makes me feel so guilty that I can’t do more. Agents have been pursuing us because of the blog, and we are trying to decide who to go with. We do not see eye-to-eye about certain things, and we’re still having constant communication breakdowns. I woke up in a sudden panic at 4:00 A.M. and I couldn’t breathe. I felt like everything was out of control and falling apart. Zak calmed me down, and helped me slow my breathing, but my mind wouldn’t stop racing. I changed into my running clothes and went running up and down the West Side Highway for five hours. Five hours. I’ve never run so far or for so long in my life. I wanted to wear myself out to the point that there was no energy left for worry or stress.
August 4, 2013: Zak was worried about my panic attack, so he booked us a room at the Standard Hotel for the weekend. Being with him was just the calm I needed to unwind and relax, away from the pressures with Tim, the lawyers, and the media. Every experience we have together continues to come with such ease and joy, and the relationship continues to get better with each day. Like me, Zak is a kid at heart: We had lots of silly moments that weekend, like romping around the hotel wearing fake moustaches and ridiculous outfits, and spontaneously dancing in the middle of the lobby.
Tim called and became angry when he found out I was at the Standard with Zak. He couldn’t believe I was taking the weekend off when we had so much to do. I know it’s unfair of me when he is doing so much, but I tried to explain to him that I needed a break for my own sanity.
August 5, 2013: Today, Zak and I sat on the rooftop of the hotel overlooking the New York skyline. I was telling him the most embarrassing story from my past, and he stopped me mid-sentence and told me he was in love with me. I couldn’t wait to say it back. It’s hard to put into words my feelings for him; I am not even sure there are words for those feelings. If there are, I certainly could not say it in a concise way. The best I can come up with is that it feels like we share a secret, like we understand each other in a way that no one else does. We see the world in a way that no one else sees it. Everything in life seems possible with him, like we could take on the world as long as we are together. He gives each new day so much excitement and meaning and joy.
August 12, 2013: Tim and I agreed to be in Los Angeles today to meet with a production studio about making a TV show based on our experiment. We also were meeting with potential agents who would represent us for film and book deals. I wanted to leave a day early since Zak was already there filming a movie, and I hadn’t seen him in a week. When I mentioned taking an earlier flight to see Zak, Tim flipped out on me. He cringes every time I say his name. He said the only reason I wanted to go to LA was to see Zak, and that I didn’t care about him or the experiment any longer. That is so hurtful to hear. Everything is so complicated now, and I wish Tim would cut me a little slack. I try not to mention Zak, but it’s difficult to never mention someone who is a huge part of my life. I wish this hadn’t gotten so messy.
August 16, 2013: These past few weeks have been a complete whirlwind. Tim and I have been nonstop in interviews, photo shoots, meetings, and magazines. It’s crazy and humbling that our little blog is being read by millions of people around the world. I have mixed feelings about all the press and attention. In part, I am thrilled that our project has reached and touched so many people. It’s unbelievable to read some of the letters our readers send us and see how it’s changed their lives. Some people say that our project inspired them to make positive changes in their own relationships, inspired them to seek therapy, or inspired them to date that friend they were always curious about. At the same time, I am overwhelmed. The other day I was recognized by strangers six times in SoHo.
I was stressed about it and went to the gym, where a girl tweeted that she was “working out across from the forty days of dating girl.” Another person tweeted that that he saw me with Zak and that I was “cheating on Tim.” I never realized how much I value my privacy until now.
August 18, 2013: Tim emailed me this morning and I didn’t know what to write back. He knows I love Zak, and I wish he had more respect for that. I hope he meets an amazing girl soon, someone who makes him realize how wrong we were for each other. I don’t want there to be any resentment or jealousy or disappointed feelings. I want him to be happy.
August 22, 2013: Today we had a session with the therapist we went to during the experiment. Tim said he thinks I am angry because he “rejected me” in Disney World. Rejection is the last thing I feel right now: I feel like I dodged a bullet. I didn’t tell him that, though. I admitted that while it’s true I may have tried dating Tim again if I hadn’t met Zak, I still didn’t think it would have worked out between us. We also talked about my frustration over his declaration of “love” for me a few weeks ago. It hurts me, because I am in a loving relationship with someone else, and I wish he could accept it and be happy for me. I just want to mend things with him. I have to remember that we are under extraordinary pressures in utterly unique, some might even say bizarre, circumstances. We need to stay strong, support each other, and work together as a team.
August 24, 2013: I was up last night until 4 A.M. working because I knew I had a long day of important work meetings and deadlines ahead. I had so much to wrap up and accomplish before I left on a four-day trip to India that Zak and I have had planned for a while now. But everything was instantly put into perspective when I was awakened by a 6:00 A.M. phone call from my mother with news that my grandmother had passed away. I canceled the meetings and the trip and grabbed a cab uptown to my parents’ apartment.
My grandmother had been sick for many years, so my emotions were mixed between sadness and relief that she is free from her pain. I spent the day with my family reflecting on memories of her. My mom told us how my grandma was a bit of a rebel growing up: always wearing red lipstick to school against her mom’s wishes, marrying a Jewish boy (she was Italian), and working outside the home—all unusual in the 1950s. She loved the simple things in life: friends, wine, fashion, and socializing. But most of all she loved her family and always tried to make us happy. Whenever I told Grandma about a guy I was seeing, she’d ask me, “Jessie, is he the one? When are you going to get married? When are you going to give us great-grandkids?” I’d say, “No, Grandma, you don’t understand; I’m way too young.” A few weeks ago when I visited her, I had felt an unexpected and sudden urge to tell her I had found an amazing man who I loved and thought I might want a future with. It was too late, though. Her dementia was so bad that she didn’t even know who I was. Times like these are a reminder of how fleeting life is and how quickly things can change. Nothing is permanent. Everything changes, evolves, and eventually dies. Impermanence can be a beautiful thing—it reminds you how precious and meaningful life is.
I was going through old photos of my grandma when I stumbled across a card my parents gave me six years ago at graduation. My mom had written me a long letter filled with wisdom. She quoted Steve Jobs, who said, “Our time is limited, so don’t waste it. You’ve got to find what you love. That is as true for work as it is for your lover. The only way to be truly satisfied is to love what you do. If you haven’t found it yet, keep looking, don’t settle. As with all matters of the heart, you’ll know when you find it, and like any great relationship, it just gets better and better as the years roll on.” In that same speech, he said that knowing you will die someday is the most important decision-making tool, as almost all external expectations, all pride, all fear of embarrassment or failure—these things just fall away in the face of death. It shows you what is truly important. As complicated as we often make life out to be, I sometimes think it’s rather simple: Find what makes you happy, and who makes you happy. My grandmother had found happiness and love with my late grandfather. Her passing, and going through all these emotions, makes me deeply cherish and appreciate the love I have with Zak, great family, and friends like Tim.
September 9, 2013: Tim and I flew to Los Angeles last week to meet with all the possible movie and TV producers. We were in back-to-back meetings all day with famous writers, producers, and movie stars. The experience was so surreal. I couldn’t believe so many people in Hollywood knew us and cared about our project. It was fascinating to get a peek inside this industry that I had always been curious about, and I was genuinely impressed by how nice and sincere everyone seemed. Tim and I have been getting along much better since our therapy session with Jocelyn, so I was finally able to take in, enjoy, and appreciate these remarkable experiences.
We flew back to New York yesterday morning and appeared on the TODAY show. Before our segment, they filmed a quick preview of us. Tim didn’t realize his microphone was on, and he leaned in toward me and said, “Oh baby, you look so hot right now.” They aired the clip with the audio for everyone to hear, including Zak, who was watching from Los Angeles. He called me and sounded a little sad. He told me it was heartbreaking to hear this from an ex-boyfriend of mine, on national television no less, but he trusts me. Zak has put up with this project and has been amazing. It can’t be easy for him to be with me while I’m posting intimate details online about a past, but still very recent, relationship. But we talked again today and he was already completely over it. This is one of the thousand things I love about this man.
While I felt bad pretty bad for Zak, I also felt terrible for Tim. Tim had only been joking, but the media didn’t see it that way. There were articles afterward calling him a “sleazy douche bag,” which is clearly not true, and I can see how much it hurts him. It has always perplexed me: Why do people love to hate and feed off other people’s slip-ups and failures? It reminds me of this quote: “Promote what you love, instead of bashing what you hate.”
September 17, 2013: After weeks of calls with various producers and studios who have been interested in turning our story into a movie or television series, we finalized a film deal with Warner Brothers out in LA. We have a talented writer, director, and production company on board. We’re going to help consult and take a first stab at doing some of the graphics for the movie. I can’t wait to see how it all pans out.
After the deal was finalized, Tim and I met up at the Soho House for celebratory drinks. Ever since the stress of posting the blog online, and the arguments we had over our entries, Tim and I have become close again. It feels great to have my friend back. Zak joined us for a few drinks, which was also a big event. It was the first time they have met. I want them to get to know each other, but neither has seemed too excited by the prospect. It would mean the world to me if they could at least tolerate each other, and who knows, maybe one day we could all hang out as friends.
October 12, 2013: Tim and I went to the premiere of Her by Spike Jonze. It was one of the best movies I’ve seen all year: It was touching, emotional, and beautifully shot. At one point Joaquin Phoenix’s character says, “I’ve been sitting here thinking about all the things I wanted to apologize to you for. All the pain we caused each other. Everything I put on you. Everything I needed you to be or needed you to say. I’m sorry for that. I’ll always love you and you helped make me who I am. I just wanted you to know there will be a piece of you in me always, and I’m grateful for that. You’re my friend to the end.”
I looked right at Tim during this moment. It sums up pretty well how I feel. I do feel in a large way that the experiment and experiences we’ve been through have changed me and helped shape who I am. I feel sorry for all the pain we caused each other when we got caught up in all the media attention. What we went through was crazy and complicated, but that’s life. I feel lucky we stuck together through it all, and came out of it even closer as friends.
October 18, 2013: I’ve been visiting Zak every weekend in Los Angeles this past month. I take the late-night flight from JFK out to LA on Friday nights and return on the red-eye on Sundays. It’s been tiring, but every moment with him makes it worth it. I promised to make him a love letter for every day we spend apart. We both travel often for work, so there will always be a lot of time spent apart in our relationship. Quite ironically, today I finished his fortieth letter. Oh, the crazy things we do for love.
Tim was also supposed to come out to Los Angeles this weekend to visit a love interest. He’s been pretty excited about this girl who lives out here. The other night, she canceled on him. I felt pretty terrible about it, so I changed my tickets to fly into LA earlier with him. We had lunch and then a nice dinner, and we enjoyed a few drinks afterward at one of our favorite spots, the Palihouse. Tim managed to pick up our waitress and secure a date with her the next night! It continues to impress me how easy it is for him to pick up girls.
The weekend was full of amazing experiences with Zak. He had had a tough week at work so I wanted to surprise him with a little getaway. I rented an Airbnb apartment for a night in the Hollywood Hills. Zak had the silly idea that I should try to hike up to the Hollywood sign. What a disaster! The hill going up to it is never-ending and only gets steeper and steeper. I was stubborn and kept wanting to climb, until we realized there were helicopters all around us and a guy on a loudspeaker was telling us we were trespassing and could be arrested! We hid from the cop cars, snuck into our car, and drove off. He told me this weekend that he hopes to spend his life with me. I was a little taken aback, but I have been feeling the same.
November 1, 2013: Things have been going so well with Zak that we spontaneously decided to live together. We moved in today. We both lived in studio apartments, and we’d been talking for months about the dream of one day having a separate bedroom, so we looked in Brooklyn, where you can get more space for your money. Plus it’s filled with artists and creative types and some of my favorite restaurants and shops. We ultimately found an amazing place in Williamsburg, where almost all my friends live. Now the only friend I have left in Manhattan is Tim.
December 19, 2013: Tim and I met with one of the producers of our movie at the Bryant Park Hotel. Afterward we went to Lady M and had some green tea cake and talked about life and love. It was just like old times when we’d do our weekly catch-ups after teaching classes at SVA. Tim seems a little upset with himself that he is still messing around with several different women, and frustrated that he hasn’t found a great girl who holds his interest. I’m proud of him because he seems to be making an honest effort to be more careful about his actions. I told him to go easier on himself. As long as he is being honest with these women about his intentions, he’s not doing anything wrong. But it seems that, more than ever, he really craves meeting an amazing girl who blows him away. Tim also talked about wanting to be a father someday soon. Tim’s talked about this before, and I always told him he was crazy! Life is complicated enough as it is, and I have never had a strong desire to be a mother. Well, as we were talking about it, I suddenly realized how much my perspective on this subject has changed. I guess being with Zak has brought out some sort of maternal instinct in me. I am actually starting to think I might want a family one day.
December 23, 2013: I can’t believe where the time has gone. It’s been over seven months since I met Zak. Our love has matured; the passionate “honeymoon” phase is over. I knew this would happen, because it happens in every relationship. I read an article about scientific studies that show that passionate love usually only lasts during the first six months, when our brain is releasing dopamine. When those dopamine levels taper off, many relationships start to go downhill. You start to feel like the other person is not making you as happy as they once did. But it’s not our partners who have changed; it’s us. We’re just not as happy as we used to be when the dopamine was high. This lower state allows us to become more bothered by the other person’s flaws, and everything begins to feel more routine.
I’ve experienced this all too many times in the past. But with Zak, it feels entirely different. I’ve certainly come down from the “love high,” but my affection and love for him still grow. As our lives become more intertwined, I realize more and more with each passing day that he’s my ultimate companion. No matter where in the world we are together, with him it always feels like home.
For his birthday I decided to surprise Zak with a getaway to Tulum because it’s where we first started falling in love. Without revealing anything at all, I was going to whisk him away in a cab to JFK, but it didn’t pan out. At the last minute he was offered a lucrative job and, still oblivious about my surprise, he took it even though he had promised not to work on his birthday. When I revealed all, how the flights and hotel were already booked, he canceled. We still had an amazing trip and stayed in clay huts on a beach called Coco Coco.
January 12, 2014: Zak and I got engaged this morning, and I couldn’t be happier. We’ve talked about spending our lives together, so while it shouldn’t be a surprise, I somehow am in a bit of shock. I guess I didn’t expect it to happen so soon!
Right after his proposal, he had to leave for the airport for a job in Guatemala, where he’d have no cell phone service. He called me from the airport right before he had to board the plane—he wanted to tell me one last time how much he loved me. I feel like the luckiest girl on the earth, and I am glad I never gave up on my search and never settled. I am glad I did the experiment with Tim, which in many ways led me to meeting Zak. I cried for joy after that call. I just can’t believe this is all actually happening to me! I texted him right after.
January 14, 2014: To most of my friends, the engagement was not a huge surprise. My sister, who has been the harshest critic of every boyfriend I have ever had, said she knew right after she met him that he was going to marry me. He’s the first guy I’ve dated who she loves and approves of. My parents are thrilled. The only person left to tell was Tim, and I wasn’t sure how he’d react. We had plans to meet up with a group of our friends at Kingston Hall in the East Village last night. I didn’t want to tell him at the same time as everyone else—I wanted to be more personal than that. When he arrived at the bar I pulled him aside, bought us a round of champagne, and told him the news. He seemed taken aback, but genuinely happy, and he gave me a big hug. Next thing we knew, Beyoncé showed up at the bar and was standing right behind us! We drank champagne and whiskey with our friends, the same group of friends we went to Miami with last December when we first came up with the idea of 40 Days of Dating. The whole crew was there: Lotta, Dan, Michael, and Maayan. We talked about how crazy this past year has been and how remarkable it is we have stayed friends through it all.
February 14, 2014: Zak was in Los Angeles today for work, so I had no Valentine’s plans. He still made the day special by mailing me the sweetest letter and a planter of roses and hiring a guy with a very heavy Indian accent to sing me a Valentine’s song. I couldn’t understand a word of it, but it put a big smile on my face the rest of the day. In the afternoon, Tim texted, asking me if I could grab a drink after work before I left for Montreal. Some coworkers pointed out that it was strange that Tim and I were hanging out on V-day, though I didn’t think much of it. I emailed Zak just to make sure he was okay with it. He sent me this reply:
There is nothing sexier than a man who doesn’t get jealous.
Tim and I met up and we reminisced about everything we’ve been through this past year. It was a year ago that we made the final pact to do the 40 Days experiment. At that time, I was frustrated and lost and ready to give up on love and dating. Wow, how much a year can change everything. Life moves so quickly, and it’s easy to fall into daily routines and just go through the motions of life. I’ve had months go by in a blink of an eye and I couldn’t even tell you what happened. This experiment with Tim allowed us forty days out of our lives to pause and reflect. To analyze behaviors and patterns and to learn more about ourselves, dating, and love. We took a huge risk together, and while our romantic relationship didn’t work out, the experiment was a success.
They say everyone you date is either a blessing or a lesson, and I think Tim was both. While at times we drove each other nuts, we challenged each other in ways that most friends never have the courage to do. The experiment made us more self-aware and stronger. Seeing how we interpreted the same experiences so differently was enlightening. No matter how clear we think we are in our words, it’s almost impossible to know exactly how someone is feeling or what they are thinking or how they will perceive us. This has given me more empathy and patience, and has helped me stop overanalyzing situations. The experiment also helped me focus on what I wanted and it gave me confidence and clarity, and shortly afterward, I met Zak. Coincidence? Fate? Who knows. Life is kind of crazy like that.
April 29, 2013: I thought about that Groucho Marx quote, the one that Woody Allen recalls in Annie Hall: “I wouldn’t join any club that would have me as a member.” My goodness, is this me? Is this why I walked away from Jessie? I feel like there’s an internal struggle between logic and the heart going on in me. If I’m so sure we’re not right for each other, then why do I feel so sad about this today? Why do I miss her so much? Will I regret this? A big part of this is guilt. I feel guilty for hurting her. I feel guilty for not being able to live up to some expectation. I feel guilty for not walking away from this experiment 100 percent “cured.” I’m glad we don’t have to analyze our relationship anymore, like we did during the experiment, but I wonder if Jessie and I will stay close. We’re so close right now, and I feel like we’ll always be there for each other. However, I know that the minute she or I gets into a new relationship those ties will change. It’s very weird to not have to see or talk to her today. She texted me late last night to say how much she liked the gift I gave her. It was sweet. I wanted to call her, but I didn’t know what I would say. This may sound ridiculous, but I wanted her to call me last night and fight for me. But she just let me go. Maybe she knows we’re not right deep down? Maybe she was expecting me to fight for her? Maybe she’s just fearing more rejection? After all, Disney World wasn’t exactly a party. I didn’t leave her with any grand gestures of hope. The strange thing is, I was never convinced that her feelings were truly about me. Did she love me, or was she just in love with love? I think we all want that, this idea that if the person we are with couldn’t have us then they couldn’t bear to have anyone. Even if that’s not true, we still have the fantasy.
May 5, 2013: I was talking to my married buddy today. He thinks I’m an idiot for letting Jessie go, but I can’t force something that doesn’t feel right in my heart. He was being like those people who judge a person based only on externals, who say a beautiful celebrity is “amazing” or a “dream girl,” but they don’t know them. That person has no idea how they’d vibe with someone like Angelina Jolie, or if she’s a raging psycho in real life or not. Some people just assume that if it looks good on paper everything should work out. While my buddy is a great guy, with great advice, he’s still unhappily married, and I need to remember to take what he says with a grain of salt. I like this funny quote: “Never trust a married guy’s taste in women. It’s like asking a starving guy what food tastes good.” Anyway, I’m still not sure about my decision to let Jessie go, and even though a good part of me knows that we’re better as friends, I can’t deny that I do miss her.
May 11, 2013: Today was the first time Jessie and I have seen each other since Day Forty of the project. We met to brainstorm and go through the journals we’d kept during the forty days. While we were talking, her phone began to buzz. I looked at the phone, and what did I see? A notification of an OkCupid message! Ha! Wow, it’s been only a week and a half, and she’s already back at it. I knew that’s how it would be. Jessie doesn’t play around—she goes right into reactionary mode. I gotta let it go and not worry about it. Toward the end of our meeting we were hugging and talking about giving it another chance between us. Honestly, knowing that she can run on to the next thing so quickly is a problem for me. It’s clearly my issue more than hers. Anyway, we said that we missed each other, and we hugged for a while. I wanted to kiss her, but I didn’t. I knew that would make everything way more confusing. She gave me a kind of ultimatum, that we should either be friends and not talk about this stuff any longer, or we should date and give it a chance. I told her I thought it was best to stay friends. Okay, I said that, but why do I still feel so confused?
June 5, 2013: There is a lot of work to be done, still, in the creation of the 40 Days website, putting the writing and photos together, editing videos, and making the illustrations. That, coupled with an enormous amount of client work I currently have, has been stressing me out lately. I know I don’t handle it well sometimes. Also, I’m noticing how different Jessie and I can be in the way we approach work. Sometimes we don’t know how to navigate each other. I feel like Jessie keeps giving me a hard time about when we’re going to launch this. I can get impatient, but Jessie can, too. She wants to launch it now, but we really need more time to craft everything. I feel a lot of pressure from her. Then, she’ll apologize for everything, completely change her tone, and become super accommodating—as if nothing has happened. I know she is just trying to be nice, but I get annoyed by the way she switches tones so quickly. I need more time to process everything. But then we begin to argue again. It’s been pretty stressful. I hope we can sort it out.
June 10, 2013: It’s been a month and a half since the experiment ended, and I’ve had no desire to resort back to my old dating ways. Recently I went on a date with a girl who my buddy set me up with. She was the first woman I’ve seen since Jessie, and she was the exact opposite of her: We ate doughnuts, drank beer, and watched the NBA finals. These are things Jessie would never be interested in, so I think I was immediately smitten by it all. We ended up sleeping together that night, and I realize how the whole thing was just some sort of rebound for me. I felt weird about it, but I tried to hang out again two nights later just to make sure. She even made me two bags of cookies, one with a San Antonio Spurs logo and the other with a Miami Heat logo, since these were the two teams playing in the NBA Finals. We had a lot of fun, and I liked her, but I knew it was a mistake. I went out with one other girl who kept saying, “Do the damn thing!” all night during dinner. Seriously? Really, eight times in one night?! I sent her home in a cab.
June 15, 2013: Jessie and I hung out with some mutual friends last night at a cocktail party. As much as I’ve been trying to deny the feelings I have for Jessie, I still keep questioning myself and wavering. I’m obviously still attracted to her, and there’s so much we have in common. Also, having a great friendship as a foundation is such an important part of any relationship. Being back in the dating game hasn’t helped, either. All that careless fun I like to have has been utterly disappointing. I’d really love to find someone special. Gosh, I haven’t had that thought in years, while I’ve been happily coasting from one date to the next. Now I can’t help but wonder: Did I make a mistake? Am I seeing things more clearly now that we’re unburdened by the parameters of the experiment? Or am I simply more interested because she’s recently gone on a couple dates with some new guy? Jessie has stopped taking the sleeping pills she was taking during the experiment, and she seems so much happier and balanced now. This has undoubtedly changed my outlook on the possibility of us, too. Anyway, we shared a cab home from the party, and she ended up telling me that she thinks that I’m crazy but that she still finds me “weirdly attractive.” Well, guess what, Jessie? I think you’re crazy, and I still find you attractive, too. Then she immediately told me that she shouldn’t be telling me that stuff. I wanted to kiss her on the spot. But I didn’t. I knew that would open a whole bag of worms. Also, I wasn’t sure she’d reciprocate, and I didn’t want to risk that rejection. Oh boy, what a mess!
June 25, 2013: I’ve been wondering what would happen if Jessie and I dated in real life. We’ve been arguing more and more about trivial things, but my birthday was two days ago, and she sent me a really sweet email.
I still have major concerns about anything long-term between us, but now that the dust has settled from the experiment, I have some perspective. Everything felt so difficult during the forty days, like a slippery frog that I couldn’t quite catch. Also, Jessie is no longer taking those pills, which makes her a completely different person. So last week, late at night while I was enjoying some whiskey, Jessie and I were chatting on email. I told her everything I had been feeling, and I asked her what she thought about the idea of giving it another chance between us. Well, she wasn’t exactly keen on the idea. She told me that this is just a chase to me, that I’m only doing it because she’s moved on and has started seeing someone new. There is some truth to this: The fact that she’s seeing a guy makes me feel more pressure to make up my mind. I’m not saying this is fair, but the experiment was so hard, and I’m just curious about how we would be together without that self-imposed experiment forcing us to be together. Now, since I told her this stuff, I’ve noticed that we’ve been arguing about everything: about when to launch the project, about what we’ve written about each other, and other things. I don’t understand this; we have worked so well together for so long. But now, even when we’re not openly fighting, there’s this tension and a passive-aggressive vibe between us. At least I won’t regret not telling her how I felt.
July 3, 2013: I’m in New Orleans vacationing with my brother, eating good food, and listening to the best jazz I’ve heard in my life. I haven’t talked to Jessie in over a week. She’s been kind of coy with me. Even though it’s only been a month, I know she’s getting serious with this new guy Zak. I called her from New Orleans, and we had a nice heart-to-heart. She told me she went to Mexico with him on their third date last week! WOW. I can’t help but think how impulsive she is, at least compared to me. One relationship doesn’t work, and she’s on to the next one so quickly. Which, at the same time, is what’s special about her: Jessie doesn’t play around, she knows what she wants. This reminds me of a quote in the film Blue Valentine when Ryan Gosling’s character, Dean, says, “I feel like men are more romantic than women. When we get married we marry, like, one girl, ’cause we’re resistant the whole way until we meet one girl and we think I’d be an idiot if I didn’t marry this girl because she’s so great. But it seems like girls get to a place where they just kinda pick the best option . . . ‘Oh, he’s got a good job.’ I mean, they spend their whole life looking for Prince Charming and then they marry the guy who’s got a good job and is gonna stick around.” I wonder, is this what Jessie’s doing? Only Jessie can know what’s right for her. Despite my love for her, this is one of the reasons I had a hard time imagining us together. I really wish her the best with Zak. I just don’t want her to get hurt, that’s all. Now back to my jazz. According to Miles Davis, “Sometimes you have to play a long time to be able to play like yourself.”
July 9, 2013: Tomorrow we’re launching the 40 Days of Dating website, but today we launched through social media and other venues what we’re calling teaser videos. Essentially, they’re four fun videos we made to get people interested and curious about the project. They received an amazing reception, especially the “behind the scenes” video, which was the perfect metaphor:
The two of us are staring at each other, trying to stay focused, while everything around us (sumo wrestlers, emotions, fears, habits, etc.) is trying to distract us from that focus. We worked hard on them and spent a lot of our own money, so it was gratifying. It was nice for a change to do something more artful and abstract that didn’t involve the emotional burden we’ve been carrying through this whole thing. In a way, this project was an endurance test. We got a drink tonight at the Flatiron Lounge to celebrate the launch.
July 13, 2013: My buddy Greg just told me he’s moving in with his girlfriend. He was the last of my good friends who was single, and I’m feeling a bit more sensitive to relationships and my own single status post-experiment, especially because of this project. I still feel the way I did at the end of the forty days—I understand how awesome it is to be in a relationship with someone that you love and connect with. Anyway, now that my buddy is moving on, I feel like I’m getting left behind. It’s like that Kanye West song when he raps, “My friend showed me pictures of his kids, and all I could show him was pictures of my cribs.” Except my line would be more like, “My friend told me he’s moving in with his girlfriend, and all I could say is that I dated a girl on the Internet.” I know, it doesn’t rhyme, but you get the drift.
July 24, 2013: Tonight Jessie and I got into a heated text message conversation about our relationship and what happened at the end of the experiment back in April. I don’t even know how this happened, but I ended up telling her that I felt like I loved her at the end of the experiment. Since we’ve only posted up to Day Twelve on the blog, she has no idea yet what I wrote on Day Forty. She didn’t seem happy to hear it. We kept going back and forth by text, and I was surprised at how affected she seemed to be by the news. I realize she’s in this other relationship now, but why would telling her that I loved her three months ago, at the end of the experiment, affect her right now? Anyway, I do feel like Jessie and I have unfinished business. We (or I, at least) haven’t yet found closure. I wonder if this is healthy for us—time has moved so quickly, and we shifted gears into creative mode right after the experiment. We still haven’t had enough space or time away to reflect on it all, which has been difficult for me. It’s a funny thing, because as open as I am, I find it difficult to truly open up to someone once I know them. Maybe that’s why I didn’t tell Jessie my feelings at the end? I can easily tell my entire life to a stranger or share my feelings with friends, but once I let someone into my life romantically, I find that I put up walls. For instance, I’ve had no problem talking about my absent father or a painful breakup or a childhood experience to a group of strangers, or on the 40 Days website, but it’s difficult for me to talk about these things one-on-one with someone I care about and who actually cares about me. Mainly because I don’t think the other person can truly relate, and also because I don’t want their sympathy. Then, later, I second-guess myself.
July 29, 2013: Earlier today, Jessie told me she’s quitting the whole thing, and then she told me to “fuck off” by text. This was really surprising, because she’s normally calm and level-headed about these things. Things have been getting worse between us. Jessie is crazy busy at work, and lately I feel like I’m taking most of these calls with agents and setting up meetings for us. So I try to hold it in because I don’t want to add to the drama, but then it just comes out indirectly and we get into a big fight. Last week, we got into an argument, and we both hung up on each other at different times. There are just so many layers and misunderstandings between us, blurred lines, decisions to make, hurt feelings. Now there’s a new kind of pressure because we’ve been getting more and more publicity. When pressure builds, sometimes Jessie shuts down while I do the exact opposite—I go into full-blown annoying soldier mode.
Not only have we been doing interviews all day with the press and taking phone calls from Hollywood film studios and agents, but we’re still doing a lot of work (illustrations, etc.) on the daily posts that requires a lot of time. Not to mention, we’re both trying to manage all of this in addition to our regular work. We’re trying our best, but it’s not working out well. I also think a lot of this is connected to the “love” stuff I told her earlier in the week. I should have kept my mouth shut! But she would have found out anyway.
August 5, 2013: So I’ve been regularly hanging with this great girl for the last five weeks, and I totally blew it with her last night. She asked me to come to an event with her, and I completely forgot about it. I’ve been so busy trying to juggle everything that’s happening with 40 Days of Dating and my design clients that I’ve literally been working nonstop. I woke in the morning to see a text message that she sent around 3:00 A.M. In so many words, she said it was over. Sigh. I feel awful. We had a lot of fun together. She has been super cool with this project, too, considering she’s reading all about me on the blog at the same time as she’s getting to know me in person. A part of me wants to fight for her, but I just don’t want to make promises that I can’t keep right now.
August 10, 2013: Since that relationship ended, I’ve been feeling rebellious and disappointed by the idea of relationships in general. And on top of it all, it’s insane how many women have been reaching out to me. I never expected this—I thought my dating life would be over because of this project—but random women are coming out of the woodwork, emailing, Facebook messaging, Instagramming me notes, and tweeting at me. On the one hand, I don’t know if I have the strength to stay away from these requests. I can’t deny that it feels good, that it boosts my ego. I mean, this doesn’t happen every day. On the other hand, it’s kind of creepy. They all think they know me. I’m constantly worried that I’m getting catfished.
Some have even found my phone number, and total strangers are texting me in the middle of the night. Do they think they can change me?
Anyway, we’ve been going out to LA and meeting with agents who want to represent us, and we finally decided on Creative Artists Agency and signed with them today. I was feeling celebratory, and I love LA, so I wanted to have some fun. A woman who lives out in LA had gotten in touch with me through Facebook last week. I found her very sexy. So I told her I was in town and asked her if she wanted to hang out. She met me in my hotel lobby that night, we had a few drinks on the roof bar, and she came back to my room. I remember lying in bed with her later in the night, and I asked her why she’s single. She said, “All the guys are either my age and they’re not very serious about life, or they’re your age and they’re not very serious about me.” That made me sad.
August 12, 2013: We’re coming back from LA today, and I’m not happy about some recent arguments with Jessie. One big reason we were out there was to meet with this production studio. I know she greatly cares about this project, but all Jessie could talk about was meeting up with Zak. I mean, she was even talking to our lawyer about it. I was annoyed, and I guess I was being kind of an asshole about it, but I was disappointed. After our meeting, she wanted to go straight to see Zak, but I wanted her to have drinks with me and the rest of the team. I didn’t think it was a big deal to hang out with them for a couple hours—that’s why we were there—but she seemed to feel I was being controlling. I get it, she’s in love, but she will have all weekend to see her boyfriend! Thankfully, she joined us for drinks. I think Jessie believes I have a problem with her relationship, but all I want is for her to be focused on the project with me.
August 15, 2013: I’m feeling dizzy! The past week has been insane with interviews and meetings: CNN, Elle magazine, London Times, Fast Company, Time magazine, talk show requests, and meetings with Hollywood studios, producers, and actresses about selling the film or TV rights. All of a sudden our project is “intellectual property.” I literally can’t believe my calendar, and our 40 Days of Dating email inbox is jaw-dropping. All from this little idea? Insane and very humbling. We met a photographer at Washington Square Park for Elle magazine recently, and we got stopped about seven times by people who were fans of the project. One young girl told us that she had had cancer (and beat it!) recently, and after battling depression, she built up the courage to pursue her dreams after reading our story. It was so touching and overwhelming to hear that. The more this project has grown, however, the less control I feel I have. I wonder if all this attention (both from fans and the media) is screwing with my pysche? Here’s what I know: When you win an award for a design project, people will recognize your work. It’s a very different thing when you present your own life on the Internet and are recognized by people outside of your work. For good or bad, people seem to think we’re two-dimensional characters in a movie. Now we’re just riding the wave and trying to juggle everything that comes along with that. I couldn’t imagine being a celebrity. Your anonymity is taken away from you and everyone wants to know you and be with you and have a piece of you. No wonder so many famous people are crazy pompous asses.
August 20, 2013: Last night we had dinner with a reporter from Newsweek. It did not go well at all, to say the least. She was egging me on from the moment we sat down, and throughout the entire dinner she kept poking at the fact that some women think I’m misogynistic, and how everyone just “loves Jessie.” She clearly had an agenda, which was disappointing. There hadn’t been much confrontation from the media so far and I was not prepared for this, so naturally I started getting very defensive—which only helped her case (i.e., angry misogynist getting angry at the female journalist). At one point, I told her that I felt like a zoo animal, and that I was ready to leave because we had already spent over two hours with her. I was tired, and I felt like she was monitoring my every move, patronizing me whenever she could. She continued, making remarks when we were ordering like, “Oh, but you don’t like to share, right?” (A reference to Day Nine on the blog, when Jessie and I were at the Knicks game and I asked her to order her own dessert.) I really did not understand it. Was she projecting her own issues on the way I live my life? Is she just angry at men? She seemed interested only in stirring things up to create a story. For Jessie and me, the whole point of this experiment was to work on our issues. We acknowledged our issues and then volunteered to call attention to them in the hopes of learning and evolving from the experience. Why attack me for it? I’ve generally been okay with the criticisms, but of course it can get to me at times. As we walked away from the restaurant, Jessie told me that she didn’t like how I had behaved. Well, what does she expect? This journalist obviously had it in for me. We’ve both been getting a fair share of criticism that isn’t always easy to swallow, but it’s also very obvious that more people are on “team Jessie.” I guess it’s easy to root for the one who “loves love.” Today, Jessie agreed that the Newsweek reporter was unfair, and she wrote me a nice email.
August 21, 2013: Reliving the forty days all over again, with the world reading and chiming in, has been painful at times. Obviously, we didn’t anticipate how big this would get, so there was no way to prepare for all this. I talked to my friend Les tonight. In regards to all the press, as well as the difficulties Jessie and I are having with each other, he gave me this fantastic piece of advice:
August 22, 2013: Today Jessie and I decided to see our therapist, Jocelyn. It’s been four months since the experiment ended, and we’re constantly at odds about everything. Last week we were literally fighting about how we each interpreted an old fight between us! It’s gotten out of control, so we decided that if there’s any hope for us to continue as friends and as future business partners, then Jocelyn’s the only one who can help us right now. The pressure from this project, from the press, the demands, and the attention we’re getting from Hollywood has just become too overwhelming. We needed to hash it all out and get to the root of it all, like what happened in Disney World. I know it might seem counterproductive to open up these wounds, but they haven’t been cleaned out properly. We both felt like we needed this. Jocelyn said that so many of our issues are probably based on the fact that deep down Jessie felt rejected by me, but also that my telling her I loved her was damaging to our friendship. It was extremely difficult to go through the session, but it did feel good to discuss this with an objective third party.
September 1, 2013: When the blog first went live in July, I was getting stopped on the street once a week, but now it’s happening two or three times a day. It happens in the grocery store, on the train, on the street, in LA, you name it. Sometimes they want to take selfies with me, but usually they just say, “Hey, I love your blog!” or they ask, “Did you guys stay together?” However, lately it’s been getting a little weird. First, I noticed on Twitter that people were taking pictures of me on the street then posting them! This made me nervous, to say the least. Second, I was walking down the street tonight, and this girl from inside a restaurant sees me and runs out of the restaurant to talk to me. She was frantic, out of breath, and very excited. We took a photo together. Is this real life? I had a coffee date with a girl last Saturday, and we were walking around Williamsburg enjoying the wonderful weather. She wanted to stop by her apartment to pick something up. While I was waiting outside for her, I casually checked Twitter. I saw three different people tweet that “Dude from 40 Days of Dating is on a date in Williamsburg!” I freaked out and made us jump in a cab immediately.
Some people want relationship advice from us. Yesterday, some girl stopped me on the street by Union Square, told me all about her current relationship, and asked for my opinion. I find this particularly funny, because the very reason Jessie and I did this experiment was because we’re bad at relationships! Yet, now, people see us as some sort of “experts” on the matter.
September 6, 2013: About a month ago we signed with the talent agency, CAA, but since we’re not in show business, everything has been completely new territory for us. We’re not sure who to trust or what advice to follow. We’ve been learning on the fly. Thank goodness we have each other. Things have been going much smoother for us since we went to therapy. Even though we can still piss each other off, we’re miles ahead of where we were a couple weeks ago. It’s been really nice. Anyway, we’ve made a couple trips out to LA recently, and we went back out there this past week for meetings. Our agents put us on this crazy ten-hour-a-day schedule full of meetings, coffees, and dinners with all kinds of people in Hollywood. We’re not quite sure if we want to turn 40 Days into a movie or a TV series, so this was extremely important. We got to meet some of the most amazing people in Hollywood this week. I’m not going to rattle off all the names, but I want to say that Kristen Bell and her friend/writing partner, Laura Moses, are so cool, and some of the most fun and down-to-earth people I’ve met. Also, we had drinks with Zooey Deschanel yesterday. Of all the people we’ve met in Hollywood so far, I must admit that I was most excited to meet her. I’ve literally been listening to the new She & Him album all summer. Because of the nature of this project, everyone naturally opens up to us about their personal relationship histories. It’s been very humbling to hear this from fans of the project, but it’s been utterly fascinating to hear stories from people we consider “stars.” It’s amazing to create something that so many people, from so many walks of life, can relate to. It reminds me of this quote from the French painter Françoise Gilot: “I’ve never believed in doing work for ’the happy few.’ I’ve always felt that painting must awaken something even in the man who doesn’t ordinarily look at pictures, just as in Molière there is always something to make the very intelligent person laugh and also the person who understands nothing. In Shakespeare, too. And in my work, just as in Shakespeare, there are often burlesque things and relatively vulgar things. In that way I reach everybody.”
September 9, 2013: Jessie and I were live on the TODAY show this morning. There are no words for Matt Lauer. On Friday, we posted Day Forty on the blog, and I believe we had over 300,000 hits. All I remember is being in the green room, sitting next to CeeLo Green with a pound of makeup on my face and having Jessie say to me, “You need to do all the talking because I’m blacking out right now.” Ha! After the show, I got calls and emails from the most random people: neighbors, friends’ sisters, old lovers, old neighbors, you name it. I haven’t heard from some of these people in twenty years! Also, Jessie’s boyfriend is not happy with me. While we were doing the show, they asked us to hang out on a couch for ten seconds while they filmed us then cut to a commercial. Jessie was extremely nervous, so I told her that I’d be stupid and try to make her laugh and make her feel better. So I said something like “Oh, baby, you look so hot right now,” and as it turned out, unbeknownst to me, the mic was on. Anyone who knows me knows that I’m always messing around, and I’m always innocently flirting. I meant nothing by it! Anyway, I wouldn’t blame Zak for being upset or suspicious of me, but it was only a joke.
September 12, 2013: I’d be remiss if I was anything but appreciative, but since we were on TODAY a couple days ago, I’ve been feeling increasingly down about everything. It’s been such an unreal high the last two months: All the attention Jessie and I have received has made this the most profound and exhilarating time in my life. We’re still getting hundreds of messages from people. Some write us novels about their personal lives and their relationship history, and some are asking for advice on their own relationships.
Today I decided to answer this random girl’s Facebook message. She’s going through a difficult time in her relationship, and she wanted advice. I’m not one to shy away, so I gave her some advice! But by connecting with her, I felt like I was working on my own relationship questions post-experiment. We’re all going through the same thing in different ways, no matter who we are.
September 18, 2013: It’s official: We agreed to a film deal with Warner Brothers! We’re crazy excited to finally make a decision after a month of meetings and Hollywood courting. This is just bananas. The amazingly talented and very cool Lorene Scafaria will be adapting the story into a screenplay. I still can’t believe that our little project, with no budget, no publicist, and only a wish to share our story, has gotten to this point. We’re also about to land a book deal with Abrams very soon. Pinching myself!
September 28, 2013: Since the beginning, there has been a good amount of hate expressed toward us and this project, which is predictable, I guess. I’d say that most of the comments, about 75 percent, have been positive. I get it, because launching something so personal and controversial will inevitably bring the haters. We put our love lives out there, so in a way, we asked for this. But reading awful comments from strangers on CNN or in Time magazine is one thing. Hate coming from peers in my own industry—people I know, people I’ve had drinks with—is another thing. Obviously, it hurts. To me, 40 Days of Dating is so much more than just a design project. Thinking only as designers would have limited the project. As designers, we are able to tell great and memorable stories; we have the tools to use our lives as catalysts to connect with people of all walks of life, all over the world. That little kid in St. Louis is excited when he opens his new Nike package, or his new iPhone, just like that girl in Minnesota who is touched by our 40 Days story and after reading it feels like she has the courage to tackle her own relationship fears. This is what we can do with design. We have voices, and Jessie and I chose to use ours in a different way. We created this from the ground up, with no publicist, no budget, and no real motive beyond telling our story in a meaningful way. It was a huge risk, both professionally and personally. I think we should all use our voices and our talents to have a larger dialogue, to show the world new ways to think about life.
October 12, 2013: Jessie and I were invited to the premiere of the Spike Jonze movie Her. I was super excited about this. After the premiere, we went to the after-party at the Standard Hotel. Jessie got drunk and ended up telling me, like she always does, that she thinks I’m crazy. We shared a couple of nice moments, and I was reminded of why I love Jessie as a friend so much. As much as we drive each other crazy sometimes, and as much as I’m now sure it would never work out between us, we still have an undeniable connection. I mean, what we’ve gone through together is not natural, and we’ve pretty much worn every label two people can possibly wear: friends, lovers, exes, creative partners, and now business partners who are going through the insanity of this all together. It’s kind of amazing, actually.
October 15, 2013: Since the random hookup in LA, I’ve been on very good behavior as far as women go. I’ve gone on plenty of dates and had some nice times, but I haven’t been leading anyone on. I’m sincerely trying to meet someone I can connect with. A couple of weeks ago I met an LA girl who was in NYC for work. We hung out for the entire week. I really liked her. I made plans to go out to LA and visit her this weekend. Everything was set, plane trips were booked, and I was excited. But only days before my flight out, she canceled on me. Apparently she decided to get serious with a guy she’s been seeing on and off for the last couple months. I’m pretty shocked by this rejection. Another girl that I had a couple of good dates with turned out to have dated a good friend of mine a couple years ago, and he’s still very much hung up on her. He told me that he’d have a problem with it if I dated her. I have no interest in damaging our friendship, so I’m walking away from this one.
November 12, 2013: Jessie is moving in with her boyfriend. I was just telling someone how Jessie has learned to slow down in relationships because of the experiment. Well, I guess not. As long as she’s happy. Jessie and I had coffee today, and she broke the news that I’m not invited to her housewarming party. At first, I understood. They’re starting a life together, and they want some space. The next day it began to bother me. Aren’t there other options, like asking me to bring a date? As much as I understand, it still hurts. Jessie was sweet and ended up apologizing to me a few days later.
November 20, 2013: Okay, I think I’ve gone on a downward spiral to my old ways since I was rejected last month. On the one hand, I’m not leading anyone on, nor am I “dating” multiple people at the same time. But I am meeting a lot of different women right now, going out on many dates, having fun and sometimes being intimate, but usually always feeling disappointed. Here’s what my current dating life looks like:
1. Last month, Jessie and I were in LA having dinner with our agents. We headed over to the Palihouse for some drinks afterward. Jessie was tipsy from her usual three drinks, and I ended up hitting it off with our waitress. She had dirty-blonde hair, and oddly, she was wearing a Denver Broncos pin. I’m no big football fan, but I made a few comments about Peyton Manning, and the next thing I knew I was leaving with her phone number. I was amazed by how flirty she was with me in front of Jessie—for all she knew, Jessie could have been my girlfriend. We went out the next night and had a lot of fun.
2. A couple of weeks ago, I was out on a third date with a woman I met at a birthday party, and she said to me, “To be creative is to be fearless. There are women who will take care of you and there are women who will inspire you. Rarely will they be both. I want to be your muse.” I knew it was over then.
3. I met a very pretty woman at an industry event, we met up for drinks later that night, and she came back to my place. We went out again a week later, but she was one of these super soft-talkers and it was driving me bonkers. I literally had to ask her the same question three times to finally understand what she was saying. And she was a big fan of 40 Days of Dating, talked about it way too much, and ultimately that was a big turnoff.
4. I recently started hanging out with Alma. She has no interest in being serious with me, she’s dating other men, and she’s generally into the idea of us just using each other physically. I’ve never met anyone with that name, and I can’t help but think of that chapter “Alma” in Junot Díaz’s incredible book This Is How You Lose Her. The ending goes like this: “Instead of lowering your head and copping to it like a man, you pick up the journal as one might hold a baby’s beshatted diaper, as one might pinch a recently be-nutted condom. You glance at the offending passages. Then you look at her and smile a smile your dissembling face will remember until the day you die. Baby, you say, baby, this is part of my novel. This is how you lose her.”
5. Today, I met an absolutely gorgeous woman for coffee. She’s one of those women who makes you look at yourself and think, “Damn I’m ugly.” She lives in LA, and we first met on Facebook months ago. We’ve been periodically chatting online ever since, and she was in NYC for the weekend to see her family, who live here. We met at a coffee shop in SoHo. Apparently, some guy there recognized me and did a play-by-play convo on Twitter about my encounter with her. I only know about this because he messaged me later in the day saying, “Great to see you in action, playa!” Wow. Pretty scary, but admittedly I thought it was funny. Meta on meta on meta on meta.
December 16, 2013: Last night I heard the best feedback I’ve ever received about this project: This woman I met at a Christmas party told me that after discovering that I was a mentor at Big Brothers Big Sisters on 40 Days of Dating, it inspired her to join BBBS herself. Now she’s a mentor for a young girl. I was so incredibly touched by that. It’s just another example of why we put this out there, and how many different ways we can connect with people as visual storytellers.
In other news, the media onslaught continues. A couple days ago we were guests on The View! You better believe my mom and all her friends were excited. It was nice to see Jessie, too. For the most part, things have finally calmed down between us. However, we haven’t been in nearly as many meetings or done nearly as much press lately, so we haven’t seen each other much lately, outside of the early stage of working on the 40 Days book. It was great to see her, and really fun to talk about the experiment again.
January 14, 2014: Last night we had a reunion with our mutual design friends (all of whom were on that trip with us to Miami when we first had the idea to do the experiment). Safe to say, nothing has been the same since that trip, and it’s been a long time since all of us have been together. It was nice to see everyone. We met at a little dive bar in the East Village. When I first got there, I noticed that Jessie seemed chirpy and light, which is when she’s at her best. She immediately said to me, “Let’s go get a drink.” On our way to the bar, she told me that Zak had proposed to her the previous night and that she said yes. It seemed like she braced herself for some sort of negative comment or extreme reaction from me, but I wasn’t going to do that. Did it hurt me? Yes, but not because I think Jessie and I should be together, or that I made a mistake by not staying with her. I love our friendship, and I think we both know that we don’t belong together. I’m very happy for her and Zak. The next day, I still couldn’t quite figure out why I felt so down about it. I was talking to my buddy Greg, and he gave me some amazing advice that put it all in perspective.
Basically, what it comes down to is this: I went through a deeply profound and very unique experience with Jessie, someone who I truly care about. So now she’s going on to marry someone, and naturally I feel a bit envious. I automatically felt like I should be in love and getting married, too. However, I have to remember that we’re on different paths, and that this is her path. For good or bad, she moves quickly and it is what it is. As complex as Jessie is, she’s quite simple when it comes to matters of the heart—more so than I am. I have my own path, and this isn’t some competition. Things will happen as they happen for me.
Thirty minutes later, randomly, Beyoncé shows up at the bar we’re at! Queen Bey was straight chillin’, martini in hand, booty shaking, bodyguard lurking.
February 14, 2014: Jessie and I met for drinks tonight. We’ve been trying to find time to hang out, but I got sick early in the week, and this was the only night I could meet up. I didn’t expect her to say yes to Valentine’s Day, but she did (Zak was out of town). We hung out drinking and eating for nearly two hours, having great conversations and lots of laughs. As we were leaving, she gave me a note that she had made for me. I was pleasantly surprised by this, and I didn’t read it until I got home. I don’t get easily sentimental about this stuff, but I was completely touched by her words.
During our night out, we had been joking about how remarkable it is that we’re still so close after everything we’ve been through in the last year. It was at that moment that I realized that what makes Jessie and me so different as people is actually what makes this entire thing work. Though we have completely different styles, tempos, and energies, we work well together simply because we respect and love each other. We didn’t work out romantically, but now we have this incredible connection and a creative partnership to boot, which has made all the ups and downs worth it. 40 Days of Dating was a once-in-a-lifetime opportunity. We went for it despite the huge risk to us both personally and professionally. We went for it because we wanted to learn more about ourselves and because we had each other as friends, first, and I believe we always will.
