Ask Polly: What Am I Doing Wrong With Men?

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Dear Polly,

I used to be very overweight. I finally lost the excess pounds, and I started dating later in life. This was after earning multiple advanced degrees and getting an amazing job. I’m 30 now, and while I’m not the most attractive person to ever grace the earth, people have historically gone out of their way to compliment me on my looks. Okay, mostly my grandmother. Kidding. More importantly, I have many deep friendships with salt-of-the-earth humans that give me confidence in my ability to love and connect with others. My problem is that while I seem to occasionally be able to convince funny, interesting, intelligent, and attractive men to date me briefly, they all end up giving me a very similar response when it’s time to end things.

My first relationship was a bit tumultuous but largely one of the happiest experiences of my life. However, my boyfriend told me in the beginning that he wasn’t sure how he felt about me and had emotional baggage from his past relationship, but that I was the “most amazing girl he’s ever met,” so he wanted to try dating. When he ended things a year later, citing not wanting to be tied down, I asked for more general feedback on whether I could have done anything different in the relationship. He told me I was a “close to perfect” girlfriend but eventually conceded that I “shouldn’t date people who weren’t super into me from the start” nor people who “wanted to be single.” Okay then.

In the breakup conversation with the next guy I dated, he gave the following soliloquy: “It’s hard, because there’s this person I find so fascinating, I can talk to for hours on end, she is funny in a way that is so rare to find, and I think she’s beautiful … but I just keep waiting for the romantic feelings to come, and they never do.” (The person was me.)

The sad thing is that many of these guys seem incredulous at themselves for not wanting to pursue things with me — apologetically and half-heartedly wondering aloud if it has something to do with how bruised they are from past relationships. Meanwhile, I have to bite my tongue to not reassure them that it’s probably not their fault — it seems to be my pattern.

I have two separate hunches. One is that while my features may line up somewhat symmetrically, my less-than-perfect body and general quirkiness render me less “hot” in a way that induces romantic feelings. Period. Some girls have more of the X factor than others, and while I like to think I’ve got it, the data suggests I don’t.

My other hunch is that my friendly and kind disposition punctuated with a readiness to text back without waiting a few hours doesn’t provide the scarcity that people need to induce desire. My first boyfriend once told me that he preferred “girls who are more quiet and mysterious.”

I can always wait longer to text back, but being openhearted is core to who I am.

What do you suggest, dear Polly?


Pattern Recognizer

Dear PR,

It’s funny that your pseudonym, “Pattern Recognizer,” has the initials “PR,” because while recognizing behavioral patterns that don’t serve you well might be seen as practical and proactive, asking guys who just dumped you why they were less than 100 percent satisfied with the experience of dating you feels more like PR — as in public relations.

And that points directly to a problem you might be having with men: You operate like a publicist. Sure, you text back too quickly. Sure, you’re openhearted and don’t always hide your feelings. But you’re also very attached to sealing the deal. You want good press. You want good reviews. You want your pretty face, blown up to skyscraper size, to attract more potential clients to your door.

It’s not unusual to want these things. But the way you want these things is intense. Because you are not someone who half-asses anything. You are an overachiever and a perfectionist. Your letter is dynamic, crystal clear, and concise. You set your mind on losing weight, and you lost it. You set your mind on attaining multiple advanced degrees and an amazing career, and you achieved those goals. You know exactly how many points above average your face rates, and how many points below average your body rates, and you carry these estimates in your head at all times and use them to explain the tiniest whiff of disapproval or disinterest. You are selling hard because in your mind, you are working with flawed goods. You’d better be convincing. You’d better play up your strengths and downplay your flaws.

You are on most of the time, and you know when to backtrack or throw in a wry joke. You take a potential client’s temperature early and often, and you analyze new feedback constantly, to see what’s working and what isn’t. Your brain never rests. You can tell the second you’ve wandered off the optimal path. You can tell when an anecdote is suboptimal and must be cut off halfway through. You can see a look that says “Almost” and “Not quite” in your partner’s eyes. You know when he’s not paying enough attention. You know when to amp up the charm. You know when to back off. You say that you don’t hide your eagerness, but you do. You hide it as much as you can, but you’re so anxious to please that even when you dial it down, you’re still coming in hot, Striker.

Even your letter is, I suspect, a carefully edited, smoothed-out, chill-sounding version of the first draft you wrote, which sounded more like SERIOUSLY THIS IS KILLING ME and WHAT THE FUCK IS HAPPENING and I HATE THIS. You feel rejected. You can’t shake the suspicion that you will always be an overweight girl inside the slender girl. You can’t shake the suspicion that you can overachieve and polish and fluff and primp yourself, you can charm the living hell out of the most funny, interesting, intelligent, attractive men, you can convince almost anyone to do anything, in fact, but you will never be good enough. You will never be able to just relax. You will never be loved for exactly who you are.

Listen. You have to stop polishing yourself so vigorously and accept who you are right now, with no analysis and no improvements and no sales pitch.

Because you’ve let your hardworking, perfectionist self take over your love life, and it’s turned you into a publicist. You have to stop being a publicist. I get that you’re down to earth, an oversharer with lots of friends. I get that you see yourself realistically. But you still, deep inside, want to be better. You want to erase your physical flaws. You want to be perfect, and you want to date someone perfect. You see yourself as constantly improving, forever approaching infinity, better and better and better. If you keep asking for feedback, you will crack the code. You will satisfy your clientele. You will win the big prize of Happily Ever After.

I want you to embrace where you are right now instead. That means not analyzing whether it’s your imperfect body or your subpar ability to appear super-chill that’s fucking things up with guys. I’m beyond certain that your body is not the issue, just to be clear. I’m sure you’re too eager in the totally mundane ways that many of us are too eager, and that you’re doing your best to squelch it, yet you’ll never really succeed at coming across as chill.

I want you to consider the possibility that the more chill you seem to guys, the less likely you are to find a guy who loves you for exactly who you are right now. I want you to consider the possibility that you’re aiming to find the best possible mate on paper — the most handsome, the smartest, the most charming, the most objectively amazing — simply because this is what an overachiever does, when you should be aiming to find a guy who is utterly attuned to your particular mix of flaws and charms. Your insecurities feed your need for a “perfect” mate, someone who seems a little “better” than you (which mostly means someone who already believes himself to be better than you). Instead, look for someone who understands and values an open heart.

I’m being very direct with you because I believe that you’re strong enough to take it. But I’m also being direct because I need you to know that you’re prone to believing that you’re more in control of your world than you actually are. You’re someone who’s not going to see a therapist until you’re in a crisis. You’re not going to ask for help until you’ve needed help for a long, long time. You’re not going to admit that you feel vulnerable until your toughness drags you into a deep, dark hole. I want you to look closely at the ways that you control your own narrative in order to make it sound cheerful and victorious, and I want you to try to let go of those controls a little bit. What if you don’t have to improve anymore? What if there is no way of measuring where you stand relative to other women? What if you’re beautiful and also a little ugly, gorgeous to some and monstrous to others? What if you are incredible and also scary, exciting and sexy and also a little bit too intense to tolerate?

Because you are. We all are. And the guys who want more mystery, who want more quiet, who want a better body, who want more suspenseful waiting time between texts? Those guys can go chase one of a million self-made shadows, shiny ghosts that are always disappearing around the next corner, harpies who shriek in eerie minor chords that make every threatened, mystery-addicted dick for five square miles grow rock hard in milliseconds.

We don’t want those dicks.

We want to be complex and concrete and unnervingly real instead. We want to be monstrous and glorious and openhearted and deeply wrong. We are not publicists, and we don’t need to hire them, because we are not looking to draw in as many clients as possible, into the theater/the bookstore/the auditorium/our beds/our lives. We are not looking for the best possible human male specimen that we can find, one that matches our advanced degrees and our amazing jobs and our salt-of-the-earth friends. We are just looking for someone who makes us laugh and sees us clearly.

When someone sees you clearly, PR, you won’t think of how many standard deviations you are from the norm. You won’t consider where your face falls on an objective numerical scale of beauty, if such a thing has ever existed. You will be sparkling and lit from within. You will have way too much to say and you will say it all, and he will ask you to say even more, drunk on your scary, idiotic, gorgeous, brilliant words and your delicious, unreal, elastic body.

That is the magic you seek. It’s a sloppy kind of magic, one that does not require strenuous self-improvement. So: Do not refine your product-testing procedures. Do not edit and clarify your questionnaire. Do not sharpen the core message at the heart of your brand. Admit that you are a little odd (in ways that are neither adorable nor “quirky”). You will always care too much, and that’s not attractive to most people, because most people are really fucking weak and frightened. But seriously? Fuck them. Stop looking for hot, frightened guys because you think you’re scary, because you think you require another gold star, because you love an impossible challenge.

It should be easier than this. And it will be easier than this, the second you’ve decided that you’ve already arrived. And you have! You are perfectly cooked. You don’t have to work so hard anymore. You don’t have to convince anyone of anything. You can just be. You are already enough.


Order the new Ask Polly book, How to Be a Person in the World, here. Got a question for Polly? Email Her advice column will appear here every Wednesday.

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Ask Polly: What Am I Doing Wrong With Men?