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‘Do I Self-Sabotage When It Comes to Dating?’

Photo: Angelia Stern/Getty Images

Dear Polly,

I’m a 28-year-old woman who has only dated one person, a man 14 years older than me, for over six years in my early 20s. I haven’t been with anyone else before or after that, apart from kissing a few people I’ve met on dating apps. Those dates never went anywhere, mostly mutually. It’s been over two years now, and I’m starting to feel like something’s got to change if I’m ever going to be close to anyone again.

My older boyfriend was a Ph.D. student, a TA in a summer workshop we took together. I was attracted to him immediately. He kept it platonic during the session, but we bonded over authors like David Foster Wallace (I know, I know) and soon enough were sending intellectual, flirty letters to each other over email. This was not an older-guy predatory thing. I initiated, and he was slow and careful to make sure I felt safe.

Getting together with him was transformative for my confidence: My insecurity around being inexperienced and undesirable went away almost instantly. I thought it would be a hot fling, but he was so kind and smart and sensual. Still, I was always open to connecting with other people, even as we moved in together, met each other’s families, got pets together. And he could tell; he’d get drunk sometimes and spout insecure (but true!) things about how I wanted to leave him to be with other people while I was still young.

In many ways, it was a beautiful relationship. We laughed a lot, respected each other, and were so tender and kind with each other. He told me that he’d want to marry me, if I were ready for that, and when I went to grad school, he offered to move to stay with me. But by the end of my master’s program, my attraction to my boyfriend had waned and I wanted the chance to meet new people, so we broke up.

I assumed meeting people would come easy. I’m reasonably confident in my appearance, and I can connect enough to meet up with people. By friends’ accounts, I come off as confident and fun in social settings. Yet here I am, two-plus years out from the breakup, and I feel stuck. Even when I’ve committed hours of free time a week to dating apps, and gone on over a dozen dates, I’ve only gone on one second date. I’m not really excited about the people I meet. I could label it and say I’m just asexual, or demisexual, or something in between, but I feel like that’s too limiting. I know I’m capable of being attracted to people! But the problem might be me and the way I approach this whole dating thing. I’m not (consciously anyway) tied to a monogamist fantasy of finding the right person and settling down. I want to be a person who can love a lot and can learn from lots of different kinds of people.

I’m fundamentally baffled by how meeting people seems easy for others. What specific things are they doing to make this happen? Am I doing something wrong? My first relationship was so intense, I don’t have deep networks of friends or friend groups my own age who are dating and getting married. Is that the problem? I just don’t know what it means to find people to hook up with and “have fun.” How is anyone so confident in what they want and what they like? How do I catch up for what feels like lost sexual time?

I want to get more experience, but it also feels important to me to love special, interesting people and not waste my time. I think when I shut people down, it’s out of a reaction of: No, not you. You’re not worthy of that level of intimacy. I don’t think we could connect, because you’re not smart enough —  or cool or funny or mysterious or kind or sensual or depressive enough. Or if you are all those things, then, well, I’m so in awe that I need to make sure I tread carefully in order to make a good impression.

Specifically, the romantic prospects I meet fall into one of three categories:

• Lame — Most common. Happens out at bar. Lots of online dates. Really not attracted or interested for various reasons and actively turned off by any moves made.

• Intellectually cute enough — Pretty common. Happens with many acquaintances, going out, online dates. I recognize this person is kind of cool and kind of cute. Physically though, I feel nothing beyond wanting them to like me, because I recognize they are an appropriate person to like. If they make a move, I will be flattered, but I will probably also panic a little and run because I’m not really that excited about them. Or if they don’t make a move, I’ll be disappointed, even though I was not really into it either.

• Actually into them — Very rare. I think someone is super cool, and I have secret pangs of attraction. I probably don’t know them that well. In person, I’m coy, I try to make eye contact and look for a subtle opening to talk. Once I’ve found an opening, I try to charm the hell out of them. Once I succeed, I don’t want to ruin the moment, which risks overstaying my welcome and undoing my charm. So maybe I move on and wait for something else to happen organically. I’m waiting for my charm to have been so overpowering that they make a move, I guess. Or for us to go off somewhere alone, where something can happen. I don’t want to freak them out, though, with signals that are too direct or obsessive. I’d rather end the interaction knowing I’ve made a good impression, leaving it open.

So I guess my question is, what is going wrong with my attitudes and behaviors in these situations that has resulted in so little romantic action in my life? Where should my focus go? Should I give “intellectually cute enough” more of a chance and work on my defensive emotional response in these situations? Should I make more active moves with the “into you” folks? What are tactics for making more active moves? Is my taxonomy for thinking about these things fundamentally fucked and skewed in some way I’m not able to recognize? I recognize how centered these descriptions are on having people like me vs. actively liking others. But is this unusual? Even if it is, it feels pathological, extending to all relationships in my life. I don’t even know how I would change this about myself.

Trying to Take Down My Walls


Your first and only relationship has led you to believe that only initial strong attraction, presumed to be unrequited, with someone you view as better or cooler or more mature than you, could ever lead to love.

When it comes to love, there’s something to be said for experimentation. Even short periods of getting to know someone who doesn’t seem quite right can be illuminating. You learn what’s attractive to you, what captures your interest, and how you might want to spend your time.

Personally, I spent years holding out for a certain kind of guy. My target demographic was mostly just reasonably attractive men who were more confident than I was. I wanted to be set at ease by someone else’s self-assured behavior. I wanted to be wildly attracted straight out of the gate. I wanted to be slightly ignored. I wanted a reason to work hard. I liked hard work! I liked running after someone who was superior! As the youngest child in a family of smart, aloof humans, that felt like home to me.

But being noticed by someone who seemed as uncertain as I was? That felt uncomfortable and unwelcome. When a guy actually appeared invested in what I thought of him, that was like being lost on Mars. What am I supposed to do now? I felt self-conscious and put on the spot. There was no hard work to busy myself with! My attraction would dry up around all that freezing red dust.

It all seems so simple now. I chased the same thing in friends; I went for aloof, too-cool types and ignored anyone who was actually paying attention to me and listening closely. I wanted to follow people around, cracking jokes, inserting insights, launching into extended monologues occasionally. It wasn’t really about being present and connecting so much as feeling half-invisible but useful. I put pressure on my friends, but I couldn’t withstand the slightest bit of pressure myself.

I’m bringing friendships into this because I think a lot of women put off tackling any friendship problems until they’ve sewed up their primary love relationship. And typically, a lot of the confusion and bewilderment that’s ruling your love life also dominates your friendships. But to be clear, the goal isn’t necessarily to change what you (instinctively, impulsively, or even dysfunctionally) desire. The goal is to understand and sometimes accept what appeals to you and why it appeals to you, and then to make a little more space to investigate, to remain open to new varietals of human being. That doesn’t mean fighting your truest desires. It means opening your heart to a wider range of humans, not just because that’s a noble goal and it makes your life more interesting, but because it will help to transform you into a less rigid person.

Being rigid doesn’t just affect how you view other people. Being rigid affects how you view and define yourself. You can occupy a rigid, unforgiving space for the sake of fun, or comfort, or creativity. I endorse that practice wholeheartedly. I love hating people, places, and things for fun and profit. But it’s important to stretch and grow, too. It’s important to reach past what you naturally love, what you were born loving. It’s important to open your eyes to the full range of human experience. It’s important to really hear people when they talk instead of letting your panic or distaste or disinterest color over everything. You don’t want to block out 99 percent of humans you meet. You want to see them clearly.

So dating and friendships and your life philosophy and your identity are all wrapped up together. Understanding the layers behind these things couldn’t be more important. It will bring you more self-acceptance and compassion toward yourself, and you’ll be better able to spread that compassion to others.

Now back to your taxonomy of mates: If I were you, I’d spend more time with your middle group, the “Intellectually Cute Enough” demographic, who are “Kinda Cute” but not “Super Cool.” Your goal here is to tolerate their interest in you instead of panicking. In my opinion, you’re not even clear about whether or not you’re attracted to these people, because you’re preemptively panicking before they make a move. And meanwhile, “making a move” feels like such a weird on/off switch here. Do you have to decide about them on the spot? What about just … seeing them again in another context and observing how they behave and how you feel around them, without pressure? Even if you’re online dating, it’s possible to tell the other person, “I’m trying to make slow decisions. I need a few casual interactions before I even know if someone makes the slightest bit of sense to me. If that sounds like a waste of your time, I get it, you can move on. That’s just how I’m handling this because I know myself.”

In my humble opinion, many online dating apps are inherently screwed up these days because they’ve been forcibly smashed into a pornographic shape by the patriarchal forces in play. It’s like a sea of douche bros decided simultaneously, “If I’m going to do all this talky talk, I’d better at least get my dick wet.” But, dude, it wasn’t like that a decade or two ago. If anything, online dating implied that you were truly, earnestly looking for a long-term commitment. Most dating apps have evolved into a kind of Door Dash for ass, and while that’s perfectly helpful to those who are looking for a quick lay before retreating into a Netflixian stupor, many of these apps no longer serve a huge percentage of the population. (That said, maybe there are decent dating apps out there? If you’ve had a decent experience with a particular app, please let us know in the comments below.)

But we tackled the absurdity of dating apps last week. Consider this chapter two of How to Date Without Losing Your Shit. The title of this chapter is “Screw Standard Practices.” Slow the whole process down to a crawl. Stop focusing on this “move” that’s going to be made or not made and gather information. Focus on remaining calm and observing the other person. This is true when you’re dealing with that last Super Cool category, too. Trust me, the members of that group are no more attractive than the dudes in the Kinda Cute group. They just happen to have the advantage of triggering your overachiever mode. Like me, you want to work hard. You loooove it, in fact. You sent me a letter with bullet points in it, for fuck’s sake. And when you’re working very hard, you’re turned on. Notice that.

And experiment with this: Work hard with the Kinda Cutes and settle back into your seat and get lazy with the Super Cools. I guarantee you the Kinda Cutes will start acting as aloof as the Super Cools (thereby possibly activating your desires!) and the Super Cools will start acting as interested in you as the Kinda Cutes (thereby buying you more time to step back and consider whether or not they really are all that).

Please note that these are experiments. The ultimate goals here are to (1) stay calm and open your heart; (2) resist the urge to perform, impress, seal the deal, or fix anything about yourself or them; (3) resist the urge either to work too hard or panic; (4) enjoy yourself. Are you hearing me about that last one? If you’re going to do this love thing, if you’re going to make connections, if you’re going to get in touch with your attractions and desires, you’re going to need to get out of your head and enjoy yourself.

Figure out how to enjoy this. Instead of putting all of your energy into SEEMING “good enough” for the Super Cools or DECIDING whether to tolerate or escape the Kinda Cutes, you’ve got to put your energy into JUST BEING PRESENT. Learn how to show up and be authentic. Learn how to relax inside your jittery body. Learn how to say “Not yet” instead of “No thanks” or “Yes, let’s do this.” Learn how to define the terms of this experiment, instead of playing along with some twisted patriarchal expectation that you either give up the booty or take a walk. You’re in control here. You have choices.

And by the way, if someone doesn’t have the time to make friends along the way when they’re dating or drinking and socializing or whatever they’re doing, then they’re not worth your time, either. A lot of my actions in my 20s and early 30s were guided by this assumption that I needed to demonstrate obvious value from the jump. “THIS WILL PAY OFF FOR YOU!” I practically shouted at every man I was attracted to. “YOU WILL REAP DIVIDENDS ALMOST IMMEDIATELY.”

The second I dropped that mind-set, everything became more promising. A guy would flirt and then neg me (“Hmm, you seem demanding”), and I’d laconically respond, “Yeah. I’m probably not your type.” Sometimes this shook off a bad seed. Sometimes this made a good seed more invested.

The biggest challenge is not attracting interested men. Once you relax and bring your true self to the table, that part is easy, whether you’re talking about Kinda Cutes or Super Cools or anyone else. The biggest challenge lies in locating and sustaining your attraction to interested men who also have the potential to keep you interested.

That’s true because overachievers not only like to do hard work while being ignored, we also want to work hard for a long time before we see our work pay off. Actually, that might be true for most people. In spite of the bizarre “Will this pay off in sex or not?” ticktock of online dating, lots of people love the chase. We love to struggle to impress someone who seems a tiny bit better than us. We buy into that rom-com formula: Two people can’t be together for a solid hour and a half of screen time, but their attraction grows until they’re both losing their minds with love and desire for each other and finally THEY SAY SO! THEY KISS! IT’S MAGICAL!

Everyone needs time to get there. I think it’s great that human beings have the freedom to be asexual or anything else under the sun that feels right to them. That’s how it should be. We should all be able to describe our experiences and our needs to others without feeling judged for what we are. But I also think that our hypersexual, fast-speed culture turns people off for a very good reason. It turns people off to the point where they think they must be permanently turned off, they must not have any desire in the first place.

And I just want to advocate for desire. As an overthinker who lives in her head most of the time, I want to say that desire takes time. Passion is sneaky. It’s a slow-growing vine. And panic and fear are drought conditions for that vine. Pressure sends that vine to Mars and plants it in the cold red dust.

When you can take possession of your own timeline and take up space with your authentic self, everything changes. When you show up and assert yourself instead of struggling to impress, when you say exactly what you think instead of saying what you think someone wants to hear, when you gather information instead of monitoring other people’s reactions to you, the climate shifts dramatically. You are transported from the high desert to a cool, fertile coastal plain. Patience and compassion — for yourself and others — fertilize your vine.

See for yourself. When there are no looming questions of “What next?” and “Right or wrong?” and “Is he about to make a move?” and “How do I seem?,” you can just tune in to another human being. You can take in the small things: The way he giggles at his own bad joke. The way he pulls on his lower lip when he’s thinking things over. When you’re calm, time slows down. You have time to think your own thoughts: What does he long for? What does he wish were different? What if we weren’t here, what if we were lying on our backs on a warm rock by the ocean, what if we were wandering through an open field? What strange and winding thoughts and feelings would unravel in the sunshine, over the course of an open-ended afternoon, if we were relaxed, if we could feel the full promise of the moment, if we could share in the glory and sadness and longing of a late afternoon in late summer?

Your body needs  time. Your mind needs time. Without time, feelings harden into panic. Your primary job right now is to slow down enough to wait for your most genuine self to arrive.

Do you deserve so much time? You do. Will anyone be patient and wait? They will. Will you be able to see the value in the ones who can slow down, and be patient, and wait? That part is up to you. But don’t blame yourself if you can’t feel anything at first. Keep experimenting. Enjoy those long morning hours, watering the soil without expectation. Try to enjoy the wait so much that eventually, you can hardly remember what it is you’re waiting for.


Polly’s evil twin Molly has a newsletter; sign up here. Order Heather Havrilesky’s new book, What If This Were Enough?here. Her advice column will appear here every Wednesday.

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Ask Polly: ‘Do I Self-Sabotage When It Comes to Dating?’