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Dear Polly,

I have this guy friend, and he is without question one of the greatest men I’ve ever met in life. In the four years or so since we became friends he has been nothing but strong, smart, selfless, and surprisingly charismatic (the type that ALWAYS knows the perfect thing to say). Two years into this friendship, I got a haircut that was much much shorter than I had wanted, and I was FURIOUS about it. It made me feel silly and extremely insecure, and my female friends are the type that want me to feel pretty, but never ever prettier than they are. I asked him what he thought about it, and he said, “Well, it is short, and that’s weird, but I can see your face better.” Then he grabbed my hands and said, “You should never, ever, hide your face.” These are the type of things I usually go bonkers for, and although he hadn’t yet declared his intentions, they seemed to be clear. Unfortunately (because without the caveat this would be too good to be true), I just didn’t find him attractive. Obese, didn’t care about how he dressed, not really a slob but not put together well. One of the last nights before he returned to law school, he asked me why we weren’t together, and because this was a friendship based on candor, I told him that I wasn’t attracted to him. I very easily could have said that the distance would be an issue (it would have been) or that I wasn’t ready for a serious relationship (I told everyone I wasn’t but would’ve abandoned that mantra for the right guy in a flash), but, for some reason, I wanted him to know the things that made him less than boyfriend material in my eyes. He laughed and said, “Good to know.”

Fast-forward a couple of years, and he is at least 125 pounds lighter, is on his way to finishing law school, and has really invested in his appearance. I’m talking stylists and manicures and $700 suits. I’ve been treading water financially (working my way through dental-assistant school) and mired in a relationship with NO FUTURE (guy has no ambition, no drive and is a jerk), and he has become the talk of our social circle. He really took what I said to heart, because literally days after we had our conversation I noticed a gym membership card on his keys.

Well, this transformation completely took me by surprise, but it definitely made me more interested. I expected him to become arrogant, and he was, in some of our mutual friends’ eyes, “the total package,” but it hadn’t changed his personality one bit. We spent more time together this summer than in summers past, usually with a few drinks in hand, and I decided that I would bring the subject up again. I asked (via text) if he still felt the same way as he did last year, and he said, “Nah not really. Kinda gave up on you.” I was furious. What had changed his mind? Was there another girl that had caught his eye? I went to the bar with a couple of female friends, but after a few drinks could not get him off of my mind. I called him and asked if he wanted to smoke, went to his apartment, and after sitting on the couch together just hanging out, he made a move. We had hours of amazing sex. I was certain we were going to take the relationship to the next level. The man who had embodied so many of the qualities I was looking for now pretty much had ALL of them. The next few days went the same way. I would get off work, he would text me telling (never asking, TELLING) me to come over after work, and I would end up spending the night. I expected to see him more, but after a few days the texts stopped. Several days passed and I didn’t see or text with him. Had I scared him away? We communicated practically every day for years until that point, so I was pretty shocked by his silence. I got onto Instagram and saw a dozen or so photos of him at a few different outings with a girl who is pretty much the younger, dumber version of me. Same body type, same hair, on the body of a 19-year-old cocktail waitress.

After almost a week, we finally spoke again, and I asked him if they were serious, to which he replied, “Of course not.” But after a conversation of vague, ambiguous answers, I finally blurted out everything that I was feeling. I wanted him, and I felt like he was punishing me for not being interested in him before. He started laughing, then called me shallow. Saying that he could never date me because he “would have to get on a scale every morning” to determine if he was worthy of me. That his personality had not changed, and that a small change in physical appearance shouldn’t take my interest level from 0 to 100. He then went into lawyer mode, showing me Facebook posts from his heavy days and now; the same clever Facebook status that had gotten 30 likes when he was overweight got over 100 now that he was thin. He then became upset, near tears even, and told me that the saddest part of losing weight was that people finally complimented him on qualities he’d always had. Then he kissed my forehead and told me that my first instincts on dating him were the right ones. I’m absolutely smitten, and want to prove to him that my intentions are genuine. But are they? Should I be punished for not wanting the ugly duckling, then falling for the beautiful swan? And is he really upset, or just using my feelings for him against me?

Falling for Friend

Dear FFF,

Your story is perfect for a lighthearted romantic comedy. The formerly chubby, sloppy guy (Chris Pratt) is the protagonist and hero, of course, and you’re the super-pretty dream girl (Rachel McAdams) who would never date him. He rolls back into town all fit and successful, you swoon, and the two of you look set to live happily ever after. Except that there’s another lady in the picture, a down-to-earth librarian with a great sense of humor (Emma Stone in ugly glasses). He and she have always palled around together, and she has secretly loved him from afar this whole time. In the second-to-last scene, you two are bickering over something stupid in your car when your formerly chubby fiancé spots his librarian love in a nearby car, stopped at a traffic light. He realizes suddenly that she’s his true love. So he jumps out of your car and runs across six lanes of traffic, Frogger-style, to declare his love for her. You’re FURIOUS. You chase him down, wobbling on your eight-inch leopard-print heels and coughing on exhaust. You scream at him, but he just kisses you on the forehead and says, “I’m sorry; it just wasn’t right between you and me.” You tell him he’s a jerk and stumble away and one of your heels breaks off. Hot lawyer and secretly hot librarian kiss, smile warmly at each other, giggle. Roll credits.

Let’s never underestimate how dramatically our opinions are shaped by moronic pop-culture tropes. Because not only were you and your ladyfriends all swept up in this notion of the lovable, true-blue ugly duckling who suddenly transformed into a manicured Provider Swan, but you allowed that fairy tale to cloud your vision completely. All of your competitive ladyfriends (who don’t like you to be prettier than them) started gushing over your buddy being “the total package,” and you just couldn’t resist laying claim to him. “Hey, that’s MY guy! He’s always loved ME and now everyone wants him!” So you ignore his “Not interested” text, deliver some high-quality booty straight to his door, and then you were stunned that, instead of being awash in gratitude at your generosity in finally loving him, he wasn’t interested in living happily ever after.

Even though my first impulse might have been to say, “No big deal. You were indifferent, and then you were hot for him. Men are congratulated for their depth of feeling when they make that transition. Why should you be punished?”, there’s more to this picture. Your response to his turnaround was a little crowd-sourced. Your ideas about him shifted completely, just because he got in shape, looked destined for success, and started blowing cash on his looks. You can pretend that it was JUST the magic of attraction that was missing from the picture, but everything else you write suggests that you were influenced very dramatically not only by your own fickle tastes, but by also by the fickle tastes of your herd.

And let me be frank: The fact that you couldn’t tell whether he was genuinely upset when he “became upset, near tears” or was just manipulating you suggests that you’re not the right woman for him regardless. I think he recognizes that, even if you don’t. He was obviously attracted to you and saw you as someone he could never “get” before, but now he can see clearly that you two aren’t a real match. (Also: What happened to your jerk boyfriend? Have you been dating him this whole time?)

So it’s pretty easy to call this one, right? Shallow Hot Girl Gets Her Comeuppance, While Former Sloppy Fun Guy With a Heart of Gold Gets His Revenge, Then Rides Off Into the Sunset. He’s the hero driving away in a sporty convertible, you’re the bitch in the mud puddle with muddy leopard-print heels in your hands.

But if that’s where I land, then I’m just as susceptible to having my pea brain molded by a shitty rom-com plot as you are. Shallow girl bad! Lovable chubby guy good!

There’s more to examine here. I’ll admit that my heart IS mostly with your friend, because those were real tears he was crying — anyone who’s lost weight and been welcomed into a whole different world of love and attention (that they found haunting and upsetting) can attest to that. But I think we still need to ask more tough questions.

Question 1: If your lawyer buddy is far less shallow than you are, why did he follow you around and bask in your hot-girl attentions when he was overweight? Why was he always hoping to get into your shallow pants? Couldn’t he have turned his gaze toward the many underappreciated plus-size women in the world, instead of showering you with praise and reassuring you about your tragic extra-short haircut? And was that really the most passionate thing he ever said to you? “NEVER, EVER COVER UP YOUR GORGEOUS FACE?” Maybe you’re the one who should be weeping into your hands, that all anyone really cares about is your supreme hotness.

Question 2: If he knew you had a crush on his manicured ass and he knew he flat-out wasn’t interested (he texted you to this effect), WHY did he let you come over and hang out until you two fucked like crazy? Why did he do this not just once, but three different times? If he’s so pure and good inside, what’s with heartlessly revenge-fucking one of his closest friends? And for that matter …

Question 3: If he’s the salt of the fucking earth, why is he fucking a 19-year-old cocktail waitress and texting “Of course not” when you ask him if it’s serious? And how do you think the TEENAGER IN THIS PICTURE feels about being treated like a girlfriend just so a callous late-twentysomething can keep fucking her?

I’m not saying people of all ages shouldn’t have the sex they want with the people they want. I’m not saying guys are bad news if they merely date younger ladies or attempt to sleep with former crushes who once wouldn’t give them the time of day. And I’m certainly not saying your buddy is a BAD GUY. He sounds like a smart, sensitive guy who’s kicked his whole life into high gear and now he’s wondering how to draw a line from the life he had before to the life he has now. He’s wondering how to process his current popularity, given how dipped in shit he used to feel. I feel for him. I think he’s got a lot of work to do, to come to grips with his confusion over how fickle and fucked this world can be. I really hope he doesn’t run out and marry some empty Über-hottie who matches his $700 suit, just because his ego is running the show these days and he doesn’t know where to put all of the sadness at having to straddle two different realities.

You know what gives me hope? The fact that he resisted the urge to keep torturing you, and resisted the urge to yell at you, and resisted the urge to dismantle your value system, just to make himself feel better. I’m reassured by the fact that he opened up and almost cried to you and showed you how hard it is for him. And you know what? If you had recognized that this was real sadness he was expressing, if you were focused on him as a human being, and not focused on WHAT YOU WANTED TO WIN (the hot, total-package provider-man of your friends’ dreams), he might’ve given you a chance. I don’t mean to cast him as some kind of valiant good guy when I say that. I’m just saying, you didn’t love him for who he was. If you did, you would’ve gotten very quiet and shown him your empathy and acknowledged how hard it’s been for him, instead of thinking about your own disappointment at not getting the hot-best-friend-lover-hero-husband of your crappy-rom-com-shaped fantasies. You write, “I’m absolutely smitten, and want to prove to him that my intentions are genuine. But are they?” If you have to ask, your intentions probably aren’t genuine. You’re in lust with your friend, and you’re all worked up over this idea that he could be your prince charming, but you don’t really love him. You may recognize many of his good qualities, but until you’re also enraptured by his vulnerability and his disappointment — the heartbroken chubby boy hiding inside that slick exterior — you’re not ready to love him for exactly who he is.

And maybe he isn’t ready to love himself for who he really is, either. Maybe he’s fixed up his exterior, but his insides still feel messy and shabby, and he’s ashamed. Maybe he’s trying to keep himself happy with shallow rewards — hot teenagers and expensive suits — but he’s not all that happy. Maybe he doesn’t recognize how much you two have in common: You’re both young and ego-driven and bewildered and lost, following the dipshit herd, taking cues from our skin-deep culture instead of looking hard at what you really want and who you really want to become.

Here’s what I wish for both of you: a way to reconcile the injustices around you enough that you can give generously to the people who deserve it; a way to block out the idiotic tropes and insipid plotlines that make you ignore the richness and complexity of the real world and the real human beings in it. My wish is that you’ll learn to be vulnerable, learn to come in second or third, or better yet, not to compete at all. My wish is that you’ll learn to question your first impulse — to own, to conquer, to have more and more and more — and feel your way through life instead. When you feel your way through your life with vulnerability, without defensiveness, without grabby anxious greed over what you’re NOT getting — an embarrassment of real riches unfolds before your eyes.

Your friend told you, “You should never, ever hide your face.” But are you hiding? Are you hiding behind a bad boyfriend, or a career path you’re indifferent about, or a gaggle of competitive girlfriends who don’t genuinely listen or support who you really are? Are you hiding from what you truly want, which is much more soaring and special and might bring you far more satisfaction than being a lawyer’s hot housewife? What do you really want? Maybe you were furious about your tragic haircut not because your actual hotness matters that much to you, but because it matters so goddamn much to everyone around you. Maybe you’re sick of feeling like a pretty girl whose insides no one seems to see or care about. Maybe you don’t want to compete with your shallow herd anymore. Maybe you’re tired of feeling like a failure just because you aren’t on the fast track to pumping out babies to fill a big empty house in the suburbs.

I’m extrapolating, of course. Only you know what you truly love and what’s best for you. But I don’t think you really want to be with your friend. I think you want to be him: strong, smart, selfless, and surprisingly charismatic. What kind of a career, what kinds of friends, what kind of a life, what state of grace could you achieve that might make you feel that way about yourself?

For now, tell your friend you’re sorry for making him feel small, and give him your blessing to follow his own path. Then find YOUR path. Figure out what will make you feel strong and smart. Figure out how you can be selfless. This is your wake-up call. What do you want for yourself, so badly that it’s embarrassing to even say it? What dream breaks your heart just to think of it? Stop chasing mythical Provider Swans, and chase that dream instead.

Polly

Got a question for Polly? Email AskPolly@nymag.com. Her advice column will appear here every Wednesday afternoon.

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