How to Overcome the Hesitater Tendency
I met my new client Shea on a hidden patio in downtown San Francisco, several blocks from his office. He was thirty-five and over six feet tall. (He later told me this gives him a big advantage in the Jewish dating market in San Francisco.)
I knew very little about Shea going into the meeting. He seemed confident and charming. Sitting at our table while he stood in line to order us coffees, I tried to guess why he’d contacted me for help. Was he having trouble deciding whom to date? Did he need help ending a bad relationship? Was he trying to get back out there after a tough breakup?
He walked back over and handed me my latte. “Well, I guess I’ll start at the beginning,” he said. “I’ve never had a girlfriend. Okay, maybe one in high school, but not since then.”
I was surprised to hear how little dating experience he had. “Why do you think that is?”
“I’ve never felt ready,” he said. “First I wanted to make sure I had my job in order. Then I found a great job, but I wanted to make sure I had enough money saved to support a wife. I got close, but then I started therapy and wanted to work on myself first. I recently switched jobs, and now I feel like I won’t be ready to date until work is more settled again.”
He explained that he ultimately wanted a wife and a family, but he didn’t think he was ready for that yet. He’d reached out to me only because his parents had pressured him to get some help.
You might be nodding along, thinking, That makes sense. Good for him. He’ll date when he’s ready.
Except when I pushed him for more details, I discovered that Shea was ready. He had worked as a lawyer at a big firm for ten years and was financially stable. He was self-aware and mature. He had hobbies (he played guitar—poorly, he said). He had friends. He enjoyed a close relationship with his family.
I’ve encountered a lot of clients like Shea. They seem like they’d be a great catch, but they aren’t actively dating. I call this bunch the Hesitaters. They come to me because they feel like they should be dating, but they’re having trouble taking action. When I ask why they haven’t been going on dates, their “I’ll be ready when” excuses start tumbling out:
“I’ll be ready when I lose ten pounds.”
“I’ll be ready when I get promoted.”
“I’ll be ready once I finish grad school.”
“I’ll be ready when I have new pictures for my dating profile.”
“I’ll be ready when things calm down at work.”
We all want to improve along some dimension. But these aspirations can turn into excuses. And I get it—dating is scary. Fear paralyzes the Hesitaters: fear of rejection, fear of failure, fear of not being good enough. No wonder they avoid dating. You can’t fail at something you never attempt, right?
But people who wait until they are 100 percent ready underestimate what they’re missing out on.
You’ll never be 100 percent ready for anything, including—and perhaps especially—dating.
The urge to wait until you feel fully self-actualized is understandable. What if you meet your ideal mate too early and they reject you?
For Hesitaters, there’s a story in your head that one day you’ll wake up and feel ready. That story is fiction. That’s not how life works. Everyone feels awkward sometimes. Most people feel nervous in high-pressure situations. Many of us have a part of ourselves we don’t want to reveal to others. And yet these very same people still go out on dates and kiss people and fall in love and break up and fall in love again and get married. Eventually, you just have to get out there and start dating, imperfect as you are. Everyone else is imperfect, too—even the person you’ll end up with.
And, by the way, let’s say you do reach this so-called state of perfection you’ve envisioned for yourself—by earning that promotion or shedding ten pounds—and then enter into a relationship. Will you worry that their love is conditional? That they’ll leave you if you lose your job, tailspin, develop a ravenous cheddar cheese addiction, and gain twenty-five pounds?
When you wait to date, you’re missing out on more than you think. Economists often refer to the opportunity cost of decisions—the price you pay when you choose one option over another. If you’re facing two mutually exclusive choices, Option A and Option B, your opportunity cost is what you give up from Option A if you choose Option B, and vice versa. A quick example helps illustrate the concept.
Imagine you’re deciding between Option A, attending grad school, or Option B, continuing to work in your current job. The tuition plus living expenses for two years adds up to two hundred thousand dollars. If I asked you how much grad school costs, what would you say? “Two hundred thousand dollars,” right?
Wrong. You’ve neglected to include the opportunity cost. If you go to grad school, you can’t keep working full-time, so the total cost of grad school includes forgoing your current salary. Therefore, the real cost of grad school is two hundred thousand dollars in tuition and expenses plus the money you would’ve made over two years if you’d worked instead of going to school. That’s two hundred thousand plus two times your current annual salary.
Or let’s say you’re deciding between going to your friend Samantha’s birthday party at a bar or your coworker David’s housewarming party. When you consider the cost of going to Samantha’s party, it’s not just about the time it would take to get there, the money you might spend at the bar, or how bad your hangover might feel the next day. It’s also the opportunity cost of not being able to get to know David and your coworkers better at his party.
When it comes to dating, Hesitaters wait until they have more confidence, more money, more whatever. But they’re neglecting the opportunity cost of not starting.
The first opportunity cost is losing the chance to learn. You can’t figure out what you like (and what you don’t) if you don’t date different people. So much of dating is iterative—making incremental changes as you learn over time—especially because you’re probably wrong about what you like or value in a partner (more on that in Chapter 8). You think you want something, you try it, turns out you don’t want it, so you learn and move on. Maybe you fall for someone mysterious: the aloof bohemian Cirque du Soleil performer who once hitchhiked across Madagascar and sews their own pants. After a few months of dating, though, you realize that while the mystique is attractive at first, you want a partner who is warm and affectionate (and owns nice pants). If you’re not going on dates, you’re not getting closer to knowing the kind of person you want to be with long term.
Take my client Jing, for example. At thirty-one, she’s dating for the first time. Her family moved a lot when she was growing up, so she never established a group of lifelong friends, much less a girlfriend. In college, she was studious and shy. She made new friends, but the dating and mating rituals of college seemed impossibly foreign to her. “I didn’t know how to flirt,” she confessed. “I just never learned.”
After college, she joined an advertising agency as an intern. She worked her way up to lead copywriter. She transformed herself into someone she liked—sophisticated, funny, passionate—but she still didn’t date. She put off trying because she already felt so behind.
Now she realizes that her lack of experience complicates her search for a good match: “I missed out on experimentation. I don’t know my likes and dislikes. And now it feels a lot harder to find a partner without that information.”
Hesitaters who delay getting out there also miss the opportunity to improve their dating skills. I’m constantly surprised by how many of my clients think they should naturally know how to date. Dating is hard! And it takes time to master, just like anything else.
I tell my clients they need to get in their reps. A “rep” is a single movement (or repetition) of an exercise. At the gym, you get stronger by doing multiple reps. In dating, you get stronger by going on more dates.
When you wait to date, and sit at home thinking about how you’re not ready yet, someone like you is going on a first date. They’re practicing their storytelling abilities, their listening skills, and their French-kissing technique. They’re getting in their reps.
Jing still feels like a beginner, she told me. “I’m making rookie mistakes when I’m supposed to be ready for the game of my life.” The fact is, everyone has to make those rookie mistakes at first. You’re going to make them no matter when you start dating, so you might as well start making them now.
Dating is a bit like stand-up comedy (though hopefully with less heckling from strangers). They’re both an audience-based art. Comics often say that if they’re at home coming up with jokes, that’s just writing. It’s not until they’re in front of a crowd that they’re truly performing stand-up. Stand-up comics know that no one brings the house down the first time they step up to the mic; they need to learn by doing. That’s one of the reasons up-and-coming comedians work so hard to get stage time. Before her breakout Netflix comedy special, Baby Cobra, Ali Wong went to multiple open mics every night, practicing her set over and over in small clubs.
It’s the same with dating. You need to practice asking interesting questions, expressing yourself in a compelling way, and going in for a first kiss. Those are your reps. And you can’t work on any of these skills if you’re sitting around by yourself, “preparing.” The only way to get better at it is to actually date.
Behavioral science warns us of the dreaded intention-action gap, when we intend to do something but don’t take the steps to make it happen. Your intention is to start dating. But you may get stuck in the gap between wanting to date and doing it. To help you get started, here are some techniques from the behavioral science toolkit. They worked for Jing, who, after a number of bumbling first dates and a handful of slightly less awkward second, third, and fourth ones, entered into a relationship with her first boyfriend.
Deadlines are one of the most efficient ways to motivate someone to take action. Short deadlines work especially well. Imagine you get an email from your bank telling you to change your password. They don’t provide a deadline. How likely are you to do it? You might intend to change it, but since it seems like you can do it anytime, you’ll likely forget about it before taking action. You’ll fall into the intention-action gap.
Now imagine your bank emails you and says, “Change your password by the end of the day.” In this case, you have a short, concrete deadline. To avoid missing it, you’re likely to either change your password immediately or set aside specific time later in the day to do it. Either way, with the short deadline, you’re far more likely to take action.
Researchers have studied the effects of the well-timed deadline—short while still doable. Behavioral scientists Suzanne Shu and Ayelet Gneezy looked at how often people redeemed gift certificates to a bakery. When the certificate was good for two months, fewer than 10 percent of people redeemed it for a pastry. (The rest were too flaky!) But when the certificate was good for only three weeks, suddenly, more than 30 percent of people redeemed the coupon. In the first scenario, people held off on taking the action because they figured they could do it later. With the shorter deadline, people were more aware that they could miss the window, so they took more immediate action.
Hesitaters, it’s time to set a deadline for when you’re going to start dating. I suggest three weeks from now. That’s enough time to do what you need to do first—the pre-dating work I’ve listed below—but not so long that you lose momentum.
Once you’ve set the deadline, start doing the pre-dating work. Download the apps. Assemble a few solid date outfits. Consider going to an improv class to learn how to listen carefully and play well with others. Pay attention the next time you’re having dinner with a friend: How much are you focusing inward (How am I coming across?) versus really listening and being curious (What is this person trying to communicate?)?
And if you’ve been out of the dating game for a while: Take some flattering photos. I had a client who was terrified of online dating. She’d always say, “I just don’t have good photos for my profile.” I convinced her to invest in beautiful new headshots. Once she got the pictures back, she finally felt ready to start. She downloaded the apps, received positive reinforcement about her pics, and went on a date the next week. You certainly don’t need to splurge on professional photography. Some flattering lighting and a friend with a decent phone (oh, hey, portrait mode!) will do.
As part of your preparation, you may want to start seeing a therapist or coach. What’s been holding you back? What are your unspoken fears? What in your past is preventing you from moving forward? But going to therapy isn’t an excuse to not start dating. It’s not a quick fix. Don’t expect it to turn you into some more perfect version of yourself in a few weeks, after which you’ll be “totally ready” to date. Commit to doing your therapy work in parallel with dating.
If you publicly announce your goals to others, you’re more likely to stay focused on them. A team of researchers led by social psychologist Kevin McCaul demonstrated this in a fascinating experiment. They took students who had a particularly hard test coming up and divided them into different groups. They asked one set of students to share their target test score with their group. They instructed a different group of students to keep their goal private. They found those who had shared with others felt more committed to the goal, spent more time studying for the test, and were 20 percent more likely to reach their goal and earn their target score.
Tell two to three of your closest friends or family members that you’re going to start dating. Share your deadline with them. You’ll feel more motivated to act once you’ve made this public pronouncement because now your reputation is on the line. (Bonus benefit: Sharing your dating goals with your community opens the door for people to set you up on dates. In Chapter 9, you’ll find practical tips on asking to be set up.)
We all have different identities: daughter, friend, Beyoncé fan, runner, and so on. We act differently depending on which of those identities we lean into at any given moment. A group of Stanford and Harvard researchers found that we can actually shift people’s behavior simply by reinforcing one of those identities. They surveyed registered voters the week of an election. They asked one group: “How important is it to you to vote?” For the other, demographically identical group, they phrased the question slightly differently: “How important is it to you to be a voter in the upcoming election?” They later analyzed voting records to see who had actually shown up at the polls. They found the people who had been asked about being a voter were 11 percent more likely to have voted than those who were simply asked about the act of voting.
While people in both groups may have intended to vote, the people who were nudged to think of themselves as voters were more likely to follow through on their plan. They considered themselves voters, not just people who vote. Once that identity was reinforced, they were more likely to show up and vote.
You can use this lever to motivate yourself to start dating. Reinforce your own identity as a dater, not just someone who goes on dates. Stand in front of a mirror and say out loud: “I am looking for love. I am a dater.” Does this seem ridiculous, especially before you’ve been on a date? Of course! But you should do it anyway.
I once worked with a client named Jacob who described himself on our first call as “very fat.” He told me, “My mom is fat, my dad is fat, we’re all fat.”
He worked at a nonprofit on their learning and development team. He welcomed new employees to the company and trained them during their first week on the job. “I meet new people all the time. That’s not the problem. I just hate the idea of dating because I can’t imagine getting naked in front of anyone. So what’s the point?”
Jacob said in the past he would try to lose weight, but then he’d fall off the wagon and end up right back where he started—unhappy with his weight and still single. Every week I tried to help Jacob see himself as a dater, not someone who would start dating once he lost weight. He did the mirror exercise. He hated it, but he did it.
One day, instead of our normal session, and perhaps inspired by a recent Queer Eye marathon, I took Jacob shopping. It was time to show his body some love.
He walked out of the dressing room and said, “Wow, I almost look good.”
I laughed. With the help of a trendy teenage sales associate, we learned that he’d been buying his clothes two sizes too big. He bought some flattering new jeans, jackets, and shirts.
Over the months that followed, we found ways to improve his self-esteem by focusing on his best qualities—like his beautiful eyes and wicked sense of humor—instead of waiting for a new body that might never come.
With time, his identity as a dater grew stronger. He continued to do the mirror exercise and started to hate it a little bit less. He downloaded a dating app and tried to go on at least one date a week. One weekend, he reconnected with an old friend from college who was visiting San Francisco from Denver. When they went for a walk, he told her stories about his dating adventures. For the first time, she saw him as a potential romantic interest.
During her next trip to San Francisco, they went on a date. And then another. He visited her in Denver. And she came back to San Francisco. Fast-forward one year: He had just relocated to Denver to be with her. The last time we spoke, he was elated. He finally had the one thing he never thought he’d find: a happy, healthy relationship.
He didn’t lose weight; he lost a limiting identity. He saw himself as an active dater, not a future one. The trick was changing how he saw himself.
Start thinking of yourself as a dater, and the world will see you that way, too.
You’re not the Beatles—you don’t have to go on eight dates a week. (Get it? Like the song “Eight Days a Week”? Forgive me my dad jokes.) Psychologists Edwin Locke and Gary Latham found that setting specific goals not only makes you more likely to achieve your goals, it also leads to greater motivation, confidence, and self-efficacy.
In general, I recommend that clients go on at least one date a week. You should proactively save time in your schedule for dates. One of my clients has a goal of going on a date every Wednesday after work. It’s consistent, breaks up the week, and gives her something to look forward to. Plus, if the date goes well, she can meet up with them again that weekend.
Look, I know this is hard. You’re putting yourself out there, perhaps for the first time. It’s scary. You might get hurt. Or hurt someone else.
When a date doesn’t turn out how you hoped it would, talk to yourself the way you’d speak to your best friend. Imagine that friend called you and said, “What’s the point? This will never work. I’m just not good enough.”
How would you respond? You wouldn’t pile on the negativity, right? You’d try to give a pep talk: “Come on. It’s just one date. Good for you for getting out there. I bet you learned something, even if the date sucked.”
Learn to be your own cheerleader. Learn to use that compassionate tone with yourself.
This was the key for Shea, our Hesitater from the beginning of the chapter. Through our work together, and his weekly sessions with a therapist, he learned to accept himself for who he is now instead of focusing on the person he hopes to be in the future. He’s currently single and dating. (And if you know anyone special who might like a tall, thoughtful amateur guitar player, let me know!)
Now it’s your turn. Start today. If not now, when?
EXERCISE: Complete the Getting Ready Checklist
One last thing—I’ve found that many of my Hesitater clients struggle to commit to dating in earnest because they’re hung up on an ex. But this advice holds true for all daters: Stop talking to your ex.
We can think of keeping in touch with an ex (in a romantic or potentially romantic way) as keeping a door open. You want the option to change your mind about the relationship. That instinct, like so many others explored in this book, is wrong. Keeping our ex around makes it harder, not easier, to move on.
Research bears this out. As part of an experiment, Harvard psychologists Daniel Gilbert and Jane Ebert created several two-day photography workshops for students. Students shot photos around campus and developed their film with the help of an instructor. At the end of the workshop, the instructor told the students they could choose one of their developed photos for a special art exhibition in London. One group of students were told they had to choose a photo to send that day and couldn’t change their minds later. Another group was told to choose a picture now, but that someone would phone in the next few days to see if they wanted to change their selection.
When the instructors asked students in the second group if they wanted to change their photos, very few of them did. But when the researchers surveyed the students, the group that couldn’t change their minds about their pictures was much more satisfied than the group that could. Why would those students be any less satisfied, especially since most of them stuck to their original selections?
While we instinctively prefer reversible decisions to irreversible ones, this flexibility often make us less happy in the long run. We’d rather be able to change our minds—return our new phone, switch our flight to a different day, reply “maybe” to an event. But it turns out, just like the students who could switch their pictures, we’re less committed to choices we think we can reverse, and commitment is crucial for happiness.
As we discussed earlier, once you commit to something, your brain starts the magical process of rationalization, convincing you that you made a good choice. You retroactively ascribe more positive traits to things you chose and more negative traits to things you didn’t. The students who had to choose a final photo committed to their picture right away, immediately launching the rationalization process. Those who had the chance to change their selection spent the week going back and forth, weighing the different options. This led to feelings of doubt, so that even when they stuck with their original photo, they felt less sure about it. When your brain accepts something and you move on, you aren’t left agonizing over the decision.
In other words, we want reversible decisions, but irrevocable ones make us happier in the long term. Keeping your ex around as a potential love interest turns your breakup into a changeable decision. Allow yourself to move on by making it an unchangeable one.
So, did you slide into your ex’s DMs last night? If you’re still carrying a torch for them and secretly wondering if you’ll get back together, try these Seven Simple Steps to Block ’Em Like It’s Hot:
Maybe this seems like too much. How harmful could it be to check their Instagram or Facebook once in a while? Here’s even more evidence from psychologists Tara Marshall and Ashley Mason. In one research paper, Marshall wrote that “exposure to an ex-partner through Facebook may obstruct the process of healing.” Mason found that talking to an ex worsens your psychological health. And for goodness’ sake, don’t sleep with your ex! Mason also discovered that “having SWE (sex with ex)” makes it harder to move on. In other words, creeping on (or sleeping with) an ex only slows down the process of getting over them.
So do yourself a favor and shut that door. Stop talking to your ex! Make your changeable decision unchangeable.