How to Create Better Dates
Jonathan made a lot of progress in our first two months working together. He started saying yes to dates with different types of people, people he would’ve rejected in the past.
One afternoon, he called me to report on his latest date: “He’s great. Passionate, brilliant, we share the same values. He has great taste in books. He loves his work.” Jonathan paused. “But it’s not a fit.”
“What?” I said, confused.
“I just didn’t feel the spark.”
“Oh, that’s too bad,” I said, deciding not to launch into a tirade against the dangerous myth of “the spark.” (I do that in the next chapter.) “What did you do together?”
“I’m really busy with work travel and a million meetings, so he met me at the coffee shop under my office before work.”
“What time?”
“Seven a.m.”
“How long?”
“About twenty minutes.”
“I see. And how were you feeling at that time?”
“To be honest, I was stressed. I was scheduled to meet with a big investor at eight a.m., so I was pretty worried about that.”
“And do you usually feel good in the mornings?”
“No, I hate the mornings. I’m a night owl. I’m a wreck until I grab my coffee before work.”
“Hmm.” I took a deep breath. I wanted Jonathan to see the situation from my perspective. “So, you’re not a morning person, you’re not awake until you have caffeine, you were distracted by an important work meeting, and yet you decided to meet with him for twenty minutes at seven a.m. for a coffee date?”
“Yep, and no spark.”
Jonathan was trying. He really was! He was busy, and yet he made the effort to date when and where he could. But there’s more to dating than simply making time for it.
Remember the story of those Google employees who cut back on their M&M’s consumption? They ate less candy once it moved from glass jars to opaque containers.
That example demonstrates one of the most important lessons of behavioral science: The environment in which we make our choices matters.
Jonathan left that seven a.m. date thinking there just wasn’t a spark between them. That there was no romantic potential. That his date wasn’t the right guy. But perhaps they’d merely met in the wrong context?
When we go on dates, we’re impacted by more than just the physical location of where we meet. The environment of a date is also when we meet, what we do, and the mindset we bring to it. When we first started working together, Jonathan treated dating as if it were an item on his to-do list, an activity to squeeze in between going to the gym and picking up his dry cleaning. He was bringing a harried, sexless mindset into dating and was then surprised when he felt no attraction to the other person. He’s not the only one. Many of my clients, desperate to find love but also busy with other commitments, have managed to drain all the flirtation and fun out of the experience of dating. Instead, they tend to engage in what I call evaluative dating (or “evaludating,” if you want to be cute about it).
And evaluative dating isn’t merely unpleasant; it’s also a terribly inefficient way to find a long-term partner. In this chapter, I’ll teach you how to shift your dating mindset from evaluative to experiential. From reviewing résumé qualities and asking, Is this person good enough for me? Do we have enough in common? to getting out of your own head and into the moment; to asking yourself, How do I feel with this person? To paying attention to what unfolds when you’re together. To dating with an attitude of curiosity. To allowing yourself to be surprised.
I’ll also explain how to create the right physical and mental dating environment to give yourself the best shot at finding love.
Imagine yourself in the following situation: You enter the room apprehensively, worried what your evaluator will think of you. You’re dressed nicely but a bit uncomfortably. You hope you’re not sweating. (Damn it. You’re definitely sweating. Back of the knees and underarms.)
You walk over to the table, put your bag down on the floor, shake hands, and slide into the seat across from them.
Would you like something to drink?
You mumble something about iced tea, no sugar. (Was that a test? What does iced tea say about me?)
The iced tea arrives.
The interview begins.
Where did you go to school?
What did you study? Why?
What’s the biggest risk you’ve ever taken?
What’s your five-year plan?
The evaluator invites you to ask her some questions.
Within forty-five minutes, the evaluation is over.
You stand up. You shake hands. You put on a friendly smile. I look forward to speaking again soon! You leave.
So tell me: Was this a date or a job interview? Instead of imagining it in a conference room, what if it’s at a wine bar? The setting might change, but the vibe is basically the same. I’m sure you’ve been on sterile dates like this one. I hear this from my friends and clients all the time: “Dating isn’t fun anymore. It feels like work.” Look, I get it, and in a way, dating is work. Dating well requires time and effort, and it’s not always enjoyable. It sucks to get rejected or find yourself let down yet again. If dating weren’t the only way to find a long-term partner, how many of us would have given up on it years ago? But just because dating requires work doesn’t mean it has to mimic what you do at work. This is not a networking meeting or a job interview. You should not conduct yourself the same way you do at work.
This type of date quells any sexuality that might enter the equation. Even worse, dates that are structured like job interviews put us into “press play” mode. That’s how behavioral scientist Kristen Berman describes what happens when we’re prompted to repeat canned responses like a robot. We launch into a story we’ve already told half a dozen times—likely on other dates—and start rattling off our résumé. In these moments, we’re just spewing out information, not connecting with the other person.
Esther Perel characterizes the anemic state of modern dating this way: “People sit there, check their pulse, and they try to see if they’re having some kind of physiological reaction—a sense of the spark. In this frozen situation, where they’re interviewing each other, they want that moment to have a blip. Are you out of your freaking mind?” If you sit through a date trying to evaluate the other person and your own reaction, you’re not present. Your date can’t get a good sense of who you are, and you aren’t present enough to experience the moment, let alone enjoy it.
The point of the first date isn’t to decide if you want to marry someone or not. It’s to see if you’re curious about the person, if there’s something about them that makes you feel like you would enjoy spending more time together.
You can design better dates—dates that don’t feel like job interviews—by shifting your mindset and selecting more intentional activities. Here’s how to make dating fun again:
Your mindset doesn’t just set the mood for your date—it can also determine the outcome. Richard Wiseman, a researcher from the University of Hertfordshire in the UK, wanted to find out how strongly our mindset affects our experiences. He recruited groups of people who thought of themselves as particularly lucky or unlucky. Wiseman gathered these people together and invited them to participate in an experiment. He handed out newspapers and asked everyone to count the number of photographs inside.
The self-described “luckies” took just a few seconds to correctly count the number of photographs. The “unluckies” took around two minutes. How did the luckies do it so quickly? On the second page of the newspaper, in large type that took up half the page, there was a “secret” message: “Stop counting. There are 43 photographs in this newspaper.” The luckies saw this clue, wrote down the correct answer, and completed the task. The unlucky folks were so busy meticulously counting the photographs that they failed to see the hint.
Wiseman didn’t stop there. He included another message, halfway through the paper, that said: “Stop counting. Tell the experimenter you have seen this and win £250.” Sadly, most of the unlucky folks missed this one, too.
Why did the lucky folks spot the first sign when the unlucky participants missed both clues? It all has to do with the way these two groups of people interact with the world. Lucky people expect good things to happen. They are open to opportunities and recognize them when they appear. When they looked through the newspaper, they weren’t just looking at the photographs with blinders on; they saw the hint on the second page.
People who saw themselves as unlucky tensed up—because they expected the worst—and their anxiety prevented them from noticing unexpected opportunities. A lucky break was staring them in the face in a big bold font, but they couldn’t see it because of their negative outlook. Their mindset became a self-fulfilling prophecy.
I’ve found “unlucky daters” behave similarly. They feel burned out after years of dating and bring that negative energy into every date. This causes them to miss great opportunities. There’s an old Henry Ford quote that goes, “Whether you believe you can do a thing or not, you are right.” Here’s my version: Whether you believe the date will go well or poorly, you are right. You’re self-sabotaging if your pre-date mantra sounds something like: “Obviously, this isn’t going to work. It hasn’t worked the last hundred dates.” You have negative-mindset blinders on! You’re adopting the mindset of an “unlucky” who misses life’s clues—in this case, the signs of a potential match.
Fortunately, we can change our mindset. Wiseman created a program called the “luck school,” where he taught unlucky and lucky volunteers to think like a lucky person. He focused on four things: listening to their intuition; expecting to be lucky; spotting chance opportunities; and rebounding more quickly when bad things happen. Assignments ranged from keeping a diary of lucky occurrences, to “visualizing good fortune,” to verbally declaring their intentions: “I am willing to put time and effort into changing my luck.” After a month, 80 percent of the luck school’s “graduating class” felt happier, more satisfied with their lives, and most important, luckier.
I want you to put yourself through your own version of luck school, shifting your mindset to expect great dates. To help you do this, design a pre-date ritual. This is something you’ll do before every date to get you in the right headspace.
Here are some pre-date rituals from my clients:
EXERCISE: Shift Your Mindset with a Pre-Date Ritual
List two pre-date rituals you want to try before future dates:
Commit to trying different pre-date activities until you find one that works for you.
Time and place matter. When do you tend to feel most relaxed and like yourself? Plan your dates in those time slots. No seven a.m. dates, please.
Stop going on dates in well-lit coffee bars. If you’re thinking: If this date sucks, at least I got some caffeine out of it. Don’t. You don’t want your dates to feel like a networking meeting. Choose something sexier, like a candlelit wine bar.
And try sitting next to—rather than across from—your date. Have you ever opened up to someone on a long drive? Or noticed that it feels easier to talk to a friend while walking side by side, when you’re not making direct eye contact? That’s because it’s easier to talk when we’re not looking someone in the eyes. Psychologists Shogo Kajimura and Michio Nomura at Kyoto University in Japan explored this phenomenon in a 2016 study. When participants stared into the eyes of a face on a screen looking at them (as opposed to one looking off to the side), they struggled to complete a simple word-matching game. Kajimura and Nomura attributed that difficulty to biology: Eye contact and processing language rely on the same neural circuitry. You can use this insight to your advantage on dates. Why not suggest going for a walk? This will help the date feel less like a job interview, protect your brain from overloading, and promote connection.
Look for a fun activity you can do with your date. Dan Ariely and a team of Harvard Business School researchers ran an experiment where they sent couples on virtual dates in an online setting designed to look like an art gallery. They hoped this setting would spark conversation, and it did. Participants chatted about the artwork and discovered common interests. The art functioned as a “third object,” something both people could comment on. A third object takes the pressure off. It makes awkward silence a bit less awkward.
If Renaissance paintings of the Virgin Mary or modern art sculptures of spiders aren’t your thing, don’t worry. It’s not about the art. Third objects can include books, games, and even other people. I recommend going on dates where you can watch your companion interact with others. This is a great way to get a sense of those hard-to-measure qualities that are so important, like kindness. Perhaps that means taking a cocktail-making class in a small group. Is your date rude to the instructor? Patient while gathering the ingredients? Helpful to the woman who showed up late? Or you could suggest a date that forces you to collaborate, like working on a puzzle or visiting a Korean BBQ place where you have to cook your own meal. How well do you work as a team? You might even consider eating something messy, like dumplings dipped in sauce. Who can put up a front when they have soy sauce dripping down their chin? In any of these scenarios, you’re gathering a lot more data than by talking one-on-one at seven a.m. in a coffee shop.
You can find a whole list of creative date ideas on my website (loganury.com).
Here are some outside-the-box dates that my clients and I have come up with:
You might even enjoy stealing this idea for a “day of yes” from a friend of mine. She explained: “We went on a date in which we took turns suggesting our next move and the other person had to say yes (unless illegal or against their values). We met at the Brooklyn Heights ferry stop, where we said yes to getting on the ferry and the next person had to suggest where to get off, to which the other needed to say yes. We kept exchanging ideas of things to do, and it was an amazing date. We ended up exploring a new neighborhood together, eating a single plate at multiple Polish restaurants, and getting in some pretty deep conversation.”
All right, admit it. Did you read that list and say, “Yeah, sure, cool ideas, but that’s way too out there for me. Who has time for that?” I understand these dates feel far more intense than a regular ol’ drinks or coffee date. But your goal here isn’t to make things as comfortable as possible. It’s to find a great person to build a relationship with. Going on dates like these is going to help you get there. Take a chance and suggest one of these activities. You don’t have to commit to a whole day of hide-and-seek, just choose something different! The worst thing that will happen is the person will decline your offer and insist on something more traditional. That’s fine, too. But a far more likely result is that your date is sick of those “job interview” dates, too, and will welcome the chance to try something new.
EXERCISE: Try Some Out-of-the-Box Activities
Take time now to think of some fun date activities. Don’t be afraid to get a little zany.
Research from Harvard Business School professors Ryan Buell and Michael Norton found that people value something more when they see all the effort that went into it.
Imagine if you were searching online for a flight. The quicker the results appear, the better, right? Maybe not. Norton ran an experiment where he had participants search for flights on a fake travel search engine. Participants were assigned to different experiment groups. For some, the program showed them immediate results. For others, the software took its time returning the results, with a progress bar that increased over time and a message about how it was searching for flights on this airline, and then this airline, and then that airline. Surprisingly, those in the second condition valued the system more. Even though it produced results more slowly, they felt the program was working harder on their behalf. They valued the effort of the program over the speed.
This is why Domino’s Pizza lets you follow along as your pizza is “fired up,” “in the oven,” and “double-checked for perfection.” We all know how pizza delivery works. But when you see effort, you appreciate value.
We can apply the same lessons to planning dates. Act more like that second travel search engine by letting your date know about the things you’ve done to make the experience special. It’s not about bragging or exaggerating; it’s about making your efforts apparent so your date can appreciate them more.
One great way to show your effort is to offer to plan the date, or to choose a place near the other person’s home or work. I’ve found that my clients who live in big cities like New York or Los Angeles often get trapped in a back-and-forth over whose neighborhood they’ll meet in. You can show effort by making the date convenient for the other person. Message them something like: “Hey, what area do you live in? I can plan something near there.” During the date, mention the thought that you put into particular decisions. Say: “I chose this Peruvian place because you wrote on your profile that it was your dream to visit Machu Picchu.” People will appreciate the effort, and your thoughtfulness will help you stand out.
Think back to the best date you’ve ever had. Perhaps you met up at a tequila bar, ate perfectly cooked carnitas tacos, and sipped spicy margarita after spicy margarita, whispering increasingly flirty things in each other’s ears, until it felt like you were the only people there, which, eventually, you were? Or did you go for a late-night walk, confess your fears about your fraught relationship with your brother, and then have him kiss away your tears, which transitioned to a full-on make-out, pressed up against your door?
What made your best date so great? Probably not the fact that your companion satisfied eight of your top ten criteria for a partner. You probably had fun! And yet fun is rarely something we build into our dates.
Enough with these robotic “press play” dates. Let’s make your dates about play.
What comes to mind when you hear the word “play”? Little kids running around a playground? Maybe you think dating is serious—you want to find a partner yesterday—and you simply don’t have time to play around.
But play isn’t just for kids at recess. And playing isn’t the same as playing games. In fact, it’s the opposite. Playing games involves deceit and misdirection. It’s a waste of time, because your love interest will discover at some point who you really are, and then what? Play, on the other hand, involves being a present, honest version of yourself—just a little lighter.
In an article in the New York Times called “Taking Playtime Seriously,” Catherine Tamis-LeMonda, a professor of psychology at New York University, explained it this way: “Play is not a specific activity, it’s an approach to learning, an engaged, fun, curious way of discovering your world.” Play is intrinsically motivated—that means it’s for its own sake, rather than achieving a goal.
Let’s say you’re on a date in the park. You might play by looking around and coming up with backstories for the people nearby. You could use these improvisational backstories to start analyzing which couples you think will last and which will break up—and why. Or you could run around and see how many dogs you can pet in fifteen minutes.
I understand this approach can feel a bit forced at first. Instead of pretending this is how you usually behave, try being self-deprecating about it: “Hey, this might sound a little strange, but what if we tried…” You’ll get points for creativity even if the person declines to participate.
Have fun. Be silly. Make a joke. Humor is a great tool to create a sense of play. When we laugh, our brains release a happy cocktail of hormones, changing our psychology. Laughing releases oxytocin—the same bonding hormone released during breast-feeding—and makes us trust the other person more. (And if it’s oxytocin we’re after, laughing is a more socially appropriate activity on a first date than breast-feeding.) Laughter lowers levels of the stress hormone cortisol, allowing us to relax. Laughter also creates a dopamine hit, activating our brain’s pleasure centers. It reinforces our behavior and makes us want to go back for more. All good things for a first date: more bonding, less stress, and an improved chance of a second date.
We form stronger connections with each other when we ask questions. Questions allow people to reveal personal details about themselves, which is essential for forming close bonds. What’s more, research from psychologist Karen Huang shows that being inquisitive tends to increase how much others like you.
The kind of questions you ask matter. Who cares what this person studied in college? Remember, this is a date, not an interview. Despite all the reasons to go deep, many of us spend our dates in the shallow end of the pool.
In the viral New York Times Modern Love column titled “To Fall in Love with Anyone, Do This,” Mandy Len Catron highlights the power of thought-provoking questions. On a date, Catron and her companion answered thirty-six questions, which escalated in intensity and intimacy from “Given the choice of anyone in the world, whom would you want as a dinner guest?” to “If you were to die this evening with no opportunity to communicate with anyone, what would you most regret not having told someone?”
These weren’t just random questions Catron had scribbled down on an index card on the way over. (Note: Never bring index cards on dates.) They were designed by psychologist Arthur Aron and his colleagues for an experiment in which they paired random strangers to ask each other a series of thirty-six questions. They tested the power of “sustained, escalating, reciprocal, personalistic self-disclosure.” Aron and his team—and later Catron, who is still with the guy from that fateful date—found that these particular questions help potential partners bond by building connection and promoting vulnerability.
If you don’t feel like asking these kinds of questions, try my favorite approach to avoiding small talk. Enter the date in media res. That’s Latin for “in the middle of things.” It’s a literary term that describes a story opening somewhere in the middle of the action, rather than at the beginning. (You can think of it as “coming in hot.”) When you walk into a date, instead of starting with the awkward “So, how’s your day going?” or “Where do you live?” jump right into the middle of things: “You’ll never guess what happened on my way over here!” or “I just got off the phone with my sister, and she told me about this battle she’s in with her landlord over the recycling bins.” By skipping the getting-to-know-you small talk and diving straight into the type of conversation that friends (or lovers!) might have, you take a shortcut to intimacy. Of course the conversation may reverse—you’ll eventually cover how your day is going, where you live, and so on, but at least you will have dipped your toes into the waters of real conversation.
Another great approach is soliciting advice. You can ask about a real thing that’s going on in your life. “My sister’s getting married in a few weeks, and I don’t know if I should give a roast or a toast. Have you ever given a speech at a wedding?” Or: “My boss sends me emails all weekend, and I don’t know how to set boundaries with him. What would you do?”
Remember, asking questions is only half the equation. You need to actually listen to the answers, too. This allows you to see how the person thinks. Does their advice resonate with you? Are they comfortable sharing? And when you respond, do you feel heard?
I once worked with a client named Andrea. She was charismatic, with long red hair and a big toothy smile. She performed improv on the weekends and would often make me howl with her tales of first dates gone wrong.
“Logan, I’m trying,” she said, crossing her arms over her chest. “I just don’t feel a connection with these people.”
“Are you practicing your pre-date ritual?”
“Yes,” she said, rolling her eyes.
“Are you planning creative dates?”
“You know I just went to that art class with that guy last week.”
“Are you doing small talk?”
“I hate small talk.”
I was struggling to see what was going wrong, so I asked Andrea to go out with a guy friend of mine to gather more information. He called me immediately afterward.
“How was it?” I asked. “Well, she talked over me the whole time, and she spent most of the date monologuing about some work drama. Oh, and she insisted on ordering for me.”
A few days later, Andrea came over again. I told her what he’d said.
“I’m so embarrassed,” she said. She was silent for a minute and then surprised me by grinning—as if the negative feedback had made her happy.
Turns out it had. “Wait, so it’s me!” she said. “It’s not something wrong with all the men in this city. It’s something I can change.”
Like Andrea, a lot of people think they need to perform on a first date. They want to make a good impression and come across as interesting. But good dates are about connecting with another person, not showing off. It’s like this quote from Maya Angelou: “I’ve learned that people will forget what you said, people will forget what you did, but people will never forget how you made them feel.” Instead of trying to be interesting, make the person feel interesting.
That means learning how to be a good listener. There’s a lot more to it than just hearing what another person is saying. Most of us listen in order to formulate our own responses, which puts the focus back on us. The goal is to understand rather than merely waiting for your turn to talk.
You can become a better conversationalist by learning to give support responses rather than shift responses. Sociologist Charles Derber identified a shift response as a moment in which you shift the focus of the conversation back to yourself. A support response, on the other hand, encourages the speaker to continue the story. For example, if your date says, “I’m going to Lake Michigan with my family in a few weeks,” a shift response would be: “Oh, I went there a few summers ago.” Even though, on the surface, you’re engaging with what your date has said, you’ve drawn the attention back to yourself. A support response might sound like “Have you been there before?” or “How did your family choose that location?” Support responses indicate that you’re invested in their story and want to hear more. They make your date feel appreciated and amplify the connection between the two of you.
EXERCISE: Practice Support Responses
Imagine you’re out, and your date makes one of the following statements. Write down a shift response and a support response to practice recognizing the difference:
Your date: “My coworker just got a goldendoodle puppy.”
Shift response:_________ _________ _________ ________
Support response:_________ _________ _________ ________
Your date: “I’m really into Ken Burns documentaries, especially the one on the Vietnam War.”
Shift response:_________ _________ _________ ________
Support response:_________ _________ _________ ________
Your date: “I’m thinking about going back to school.”
Shift response:_________ _________ _________ ________
Support response:_________ _________ _________ ________
Please, please: Keep your phone out of sight. Research from MIT professor Sherry Turkle found two negative impacts of having a phone on the table when you’re talking to someone: One, it decreases the quality of the conversation. People naturally tend to discuss more shallow topics, because there’s a fear that at any moment the phone will interrupt them. Two, it weakens the empathetic connection that forms between the two people.
Despite all the evidence that phones create a barrier to connection, 89 percent of people admitted to taking out a phone during their last social interaction. Don’t do it!
Try this approach. At the beginning of the date, ask the other person how they’d feel about both of you committing to putting your phones out of sight. You’ll show you care and increase your chances of the date going well. (You might even bring up Sherry Turkle’s research, because nothing screams “I’m good at sex” like a research citation.)
An artist I know prides himself on always incorporating a happy ending to his dates. (No, not that kind! Get your mind out of the gutter and back into this book!) For example, toward the end of the night, he’ll ask the cryptic question, “Have you ever been to San Francisco’s secret slide?” and, if his date is curious, take them to this romantic, under-the-radar spot. He understands that the end of an experience matters.
In a famous experiment, behavioral economists including Daniel Kahneman compared the experiences of patients undergoing a colonoscopy. (Don’t worry, these were all people who needed this exam, not just psych experiment volunteers.) Some patients endured thirty minutes of unpleasantness, while others experienced thirty minutes of unpleasantness with an additional five minutes of slightly less discomfort tacked onto the end. Perhaps counterintuitively, people preferred the latter experience, even though the whole thing lasted longer. That’s because of a phenomenon called the peak-end rule: When assessing an experience, people judge it based largely on how they felt at the most intense moment and at the end. Their memory isn’t an average of their minute-by-minute experiences.
So order dessert at the end of the meal. Give the other person a meaningful compliment before you head your separate ways. Take advantage of the peak-end rule.
Jonathan, like many of us, had a long checklist of criteria for his potential partner. After his dates, all he could see were the ways people fell short when stacked up against his imaginary perfect man. That “Does he check all the boxes?” mentality is yet another example of evaluative dating. Checklists aren’t inherently bad, but most people’s lists focus on the wrong things—like someone’s résumé qualities. I designed a different kind of checklist for Jonathan: one that would help him shift from an evaluative to an experiential mindset. Instead of determining if a potential match met a particular requirement, he was able, with this list, to tune in to how he felt about his dates. It encouraged him to be present and to focus on what really matters.
I urged Jonathan to answer these questions on his way home from each date:
The Post-Date Eight
Knowing he had to answer these questions afterward, Jonathan started paying more attention to how he felt during the date. He started agreeing to second dates with guys who weren’t as impressive on paper but made him feel optimistic, attractive, and relaxed. He was able to more quickly reject guys who had impressive backgrounds but left him feeling cold. He allowed himself to experience the date rather than “interviewing” the guy for the role of husband.
EXERCISE: Answer the Post-Date Eight
Snap a photo of those eight prompts and commit to looking at them at the end of every date to help you get in touch with how the person made you feel.