Ask Polly: Should I Make The First Move On My Dream Girl?

Appearing here Wednesdays, Turning The Screw provides existential crisis counseling for the faint of heart. “Spare change for when your stock hits a 52-week low.”

Dear Polly,

I’m a 26-year-old guy who has been most flatteringly described recently as “not unattractive” (I’m relatively short and quite skinny). I’ve been “enamored” with this 20-year-old friend of mine, who is on the opposite side of the sexual appeal scale. Not only is she very beautiful, she’s also very charming and fun, and has plenty of suitors due to these particular qualities. To put it bluntly, she’s way out of my league.

The problem is, I’ve been interested in this girl for over a year. Initially, I asked her out and she replied that she saw me only as a friend, but if I could accept that, she would like to hang out with me (we usually go to the movies). In the meantime we’ve grown to be good friends. I find her easy to talk to, which for me is kind of rare. My feelings for her have not subsided. And I’ve been finding it very hard to know how to deal with the whole thing.

I honestly took her seriously when she said that she saw me only as friend, but I would be lying if I said that in the last year I wasn’t trying to make her change her mind. A few months ago, she even texted me, telling me she liked me a lot, which I took to mean she liked me as her friend a lot, but nonetheless meant a lot to me as an expression of affection. When I told her all this, she said “but I do like you,” again making me wonder if I should read more into it than a mere expression of friendly affection. Given that she knows how I feel about her, the fact that when we hang out she doesn’t “make a move” tells me that she hasn’t changed her mind. If I ask her to hang out with me, she usually does, but it’s never her who asks (except once, when she asked “so, when am I going to see you?”).

She does, however, ask me to go out with her and a group of friends sometimes. But I’m what you would call an introvert, and although the prospect of spending time with her makes me want to say yes, the idea of being just one of a big group of people scares the hell out of me, especially because I dread the idea of going out because of her just to have her spend more time with other members of the group.

I even fear this is why she’s not interested in me, thinking that what she sees as my reclusive personality will be an obstacle to a relationship. The thing is, I do believe (although I might be wrong) that if I had a romantic relationship with her, I would find it easier to go out more often, as I would be going out WITH HER, even in big groups: having her there WITH ME would have a soothing effect on my social anxiety, or at least I would want to go, instead of preferring not to.

So, should I talk to her about this (I’ve often thought of doing so, but I fear it might be too uncomfortable for her)? Should I ask her if there’s any possibility of her seeing me differently, as a romantic interest, given that when she told me she didn’t, she barely knew me compared to now? Should I ask her if her reticence is motivated by pure lack of attraction (and therefore insurmountable) or by some perceived incompatibility, which could be “negotiated”? Should I just shut up and try to kiss her, like a friend of mine says? Or should I just shut up, end of story, and be happy that she is a good friend?

Guy Who Can’t Think of a Funny Way To Describe Himself


Jesus fucking Christ. You know you’re not immortal, right? This is your one chance to be alive, and you want to go down in history as the guy who can’t think of a funny way to describe himself (beyond “not unattractive”), who’s been waiting around for a YEAR for one girl? You really want to be the guy who says he won’t be able to go out with a group until he’s magically validated by the gorgeous, outgoing supergirl of his dreams?

You’re like one of those really bland princesses in the old-school fairy tales, a hothouse flower waiting in a high tower for your savior to arrive on her white stallion and whisk you away from this life of pining in isolation. But no one’s going to save you, buttercup, until you save yourself. She doesn’t like you, trust me. No one likes a human void.

You need an injection of flair and confidence and verve, stat. You need to stop feeding the scampering, scared rat parts of your brain and start nourishing the calm, swaggery lion lobes. You need to dare to describe yourself in a funny way, or a stupid way, or any way at all. You need to dare to make a mistake now and then. Rejection is part of life. Stop hiding out, fearing it. Extroverts don’t hold some special power, they just resolved not to let rejection (which they experience constantly, by the way) stop them from having interesting experiences.

I have a friend who is very reserved and not all that talkative. He’s so short and so skinny he’s almost like a miniature man. Women can’t get enough of him. He’s funny, and a good listener, yes, but he also knows how to hold himself. He exudes a calm, assertive energy — the kind of energy that the Dog Whisperer claims has the power to turn a jittery, growling attack dog into a submissive, servile puppy. I’m something of a fear biter, and I always feel relaxed if not downright giddy when he’s around. He’s confident without being arrogant, quiet without being dull, and he never says a thing about being small or short or any of that, because he just has too many hot girlfriends to worry about it.

I’m not saying you’re bad and he’s good, I’m just trying to shake you out of hiding away from the world and making excuses for yourself. I want to encourage you to envision a future self that does less waiting around and more diving in. I think you need to develop a different kind of relationship with yourself, one that leaves room for skepticism and doubt, but that doesn’t let second-guessing choke out everything else like kudzu. You need to work on calming yourself, trusting yourself, believing in yourself. You can hold your own in a group — anyone can — you just need some practice. That’s why you should go out with a group of her friends. Yes, it might be torturous and awkward, but it’ll help you to be less fearful of these kinds of situations. You should also start doing yoga, which will make you feel calmer — and, well, sexier — in your own skin. I can’t believe I just typed that. Ick. But it’s true, and you need it. You need to put on some sweats and suffer through the indignities of feeling like a giant dork in a room of sleek honey lambs.

I also want you to look in the mirror every morning and say to yourself, out loud, “Goddamn you’re a handsome devil.” I am completely fucking serious. When I went through a weird self-doubting phase, I started saying something totally absurd like that, and even when the words and my face in the mirror clashed egregiously, it put me in a kind of a giddy, fuck-the-critics mindset. The courage to drag your mediocre ass out the door sometimes comes from the strangest places. Maybe when you say it, you’ll feel a little chumpy. That’s ok. Chumpy is something. Chumpy is lovable, even. The point here is to fill the void. To be something. Dare to be something, motherfucker.

Look around you. No one knows what they’re doing, what they’re saying. Everyone is just as shy and clueless and worried as you inside. They’re simply forcing themselves to act, to speak, to claim their space on this planet.

I’m sure you’re much more appealing than you imagine. Go out there and meet some more women. Pack some yoga muscles onto that svelte frame of yours. Ask your lady friend who cuts her hair, then go to that haircutter and say, “Just make me look hotter.” (This actually works.) No more hunching, no more filling in every gap in the conversation. You have the right not to please everyone you see.

Learn to appreciate your uniqueness, and other people will appreciate it, too. It worked with this pretty girl. That means it’ll probably work with her friend, too. In fact, who knows? Maybe she’s actually been wanting to set you up with a cute-ish friend of hers, an introvert, and here you are mooning over her in your lonely apartment, wasting your time and energy on someone who very clearly stated she wasn’t interested and who hasn’t contradicted that statement since.

You need to start taking yourself more and less seriously at the same time. You need to loosen up and have some fun and stop obsessing about the things you do wrong. Just experiment in turning that part of your brain off. Ignore the voices, and live your life. This friend of yours might just end up falling in love with you — I’ve seen it happen. But even that will be doomed to fail if you don’t fall in love with yourself first. Goddamn you’re a handsome devil. Loosen up and have a little fun for a change.


Hi Polly,

I seem to find myself in this perhaps, not unique dilemma, of wondering if I only like boys if there’s a “challenge.” I’ve now been in this situation where I’ve had completely nice, good “boys on paper” like me that I haven’t pursued for reasons like “being too nice,” liking me more than I like them, or not being attracted to them. Objectively, I recognize these boys are good looking but sometimes I just don’t… feel anything. My head tells me I am being stupid for missing these opportunities to be with perfectly nice men, and my heart/gut/stomach or whatever organ that disagrees tells me I need to go with what I feel. Then I start to panic because I feel like as I get older, my opportunities for “nice boys” get fewer and fewer.

I wonder if a part of it, is because I feel like I’m only at my “best,” if I’m on my “A” game and constantly trying for something, whether it be, making sure I hit the gym 4–5 times a week, or that I look nice before I leave the apartment. Otherwise, left to my own devices and slight penchant for laziness, I would probably just sit in my messy room, overflowing with clothes, and eat cupcakes in bed. I can’t figure it out. Am I just not attracted to these completely nice guys because I am truly just not into them? Am I commitment-phobic? Do I not like guys that like me? The type of guys that I do like, aren’t even of the bad boy variety or aren’t even the best looking. I do tend to go for smart, sarcastic boys that are very “cutest guy in my AP calc class”-type so I guess that qualifies as my “edge.”

Help me, Polly! Am I totally overthinking this? Should I just give the guys who like me more than I like them a chance before fleeing?

Likes A Challenge

Dear LAC,

So glad you wrote in! Yes, you should give LW1 a chance before fleeing. Sure, he’s a little insecure and he startles easily. But once he takes up yoga and ignores the scampering-rat nodes firing away in his brain, he’s going to make an ideal mate: smart, thoughtful, a good listener, and damn funny, actually, if you’re paying attention at all.

What’s that? Your ideal guy is a lot taller and a lot snider than that?

Well, here’s a pattern I’ve noticed among heterosexual women: When you’re very young, you want a golly-gosh-shucks earnest boyfriend. About five years (and maybe two or three earnest boyfriends) later, you start to crave the very confident, snide types. Ten years after that, though, having burned through four to seven confident, snide, “I’ll settle down when I’m good and ready” types in a row, having bickered in circles with these guys, or moved in with them, or chased them around the country, you’re finally exhausted, and you want a golly-gosh-shucks earnest boyfriend again.

Even then, you can’t quite stomach the attention a golly-gosher will shower on you. You feel like there must be something wrong with him, to like you so much. He must be kind of a dud. Keep feeling that way, and watch as some really smart lady snatches him up, leaving you surrounded by snide boys whose mysteriousness seems to ferment into repetitive navel-gazing by the second.

So yeah. I would strongly encourage you to give the guys who like you a chance, be they short or tall. At first, not wondering all the time whether they like you or not will feel strange. You’ll think you must not be that into them. But the next thing you know, you’ll be totally in love and pretty damn happy. Mark my words. It’s much more relaxing to be with someone who likes your B or C self just as much, someone who’ll teach you that the whole world won’t end if you let down your guard every now and then.

There’s nothing wrong with laying around in a messy bed, eating cupcakes with a nice guy who adores you. It’s a lifestyle I strongly recommend. The A life — the clean apartment, the super-charged career, the snarky stud who’s always disappearing around the next corner — is vastly overrated and a little empty, like a pretty ad in a glossy magazine. Even when you have it, you can’t feel it. Don’t chase illusions. Find someone imperfect who really loves you. Open your heart to regular mortals. And let yourself be one of them while you’re at it.


Previously: Ask Polly: I’m Angry At My Mom And I Can’t Talk About It!

Write to Polly and she’ll solve your problems faster than you can say, “Goddamn, you’re a handsome devil!”

Heather Havrilesky (aka Polly Esther) is The Awl’s existential advice columnist. She’s also a regular contributor to The New York Times Magazine, and is the author of the memoir Disaster Preparedness (Riverhead 2011). She blogs here about scratchy pants, personality disorders, and aged cheeses. Photo by Cake Girl by Hyeyoung Kim.