Question #144: I am tempted to get a makeover so I can ask out my crush.

Mannequin Practice - Actress Devon Carson poses like a mannequin behind the scenes of the short film The Wardrobe
Production still from my film, The Wardrobe.

Captain my Captain,

I’m twenty years old, I’m in my third year of college and for the first time I have a fat – no – a phat crush on someone. I’m not new to dating or youknowwhat (well, not extremely new anyways..) but I’ve never felt so hopelessly into someone before. I guess you could say this is my first real crush.

The problem isn’t that he *doesn’t know I exist* because he does, we talk in class and around school. I just don’t think he’s into me. I’ve seen the girls he’s dated and I don’t think I’m his type. Also we only chill at school, we’ve run into each other at parties once or twice but were really just classmates.
My brain is telling me “let him be! Find another boy! You can’t force these things!” but another part of me is ready to bend over backwards to become this boy’s type. All of the sudden I have urges to get new clothes and a haircut. 

Also, I have a class with him and his recently ex girlfriend. Anytime I want to chill (…or flirt…) she comes swooping in…

Its silly. I want to either shut this whole thing down so I can concentrate on more important things (what I usually do, but this one has me hooked) or convince him that I’m actually a cool kid and move on to the next level. This secret longing bullshit is getting old. I met him a year ago! How do I move on? Or, is it wrong to change somethings about myself in order to get a dude??

– Hopeless Nerd

Dear Nerd,

I love everything about this question, because:

1) Helping geeks ask people out is one of the reasons I got into this advice-blogging business.

2) Your question allows me to directly attack the dominant cultural meta-narrative around women, desire, appearance, and agency, which is one of the reasons I get up in the morning.

You’ve committed a couple of critical errors by getting way invested in this guy, doing research about what “type” of girl he likes, and letting this crush fester for a year(!) without speaking up, but some hope remains to you. Next time you see him, say “I always run into you in class or at parties, but we never get to really hang out. Would you like to get a drink with me this weekend?”  “A drink” could be a diner breakfast, or coffee, or a movie, or an art show, or a study break, and “this weekend” could be after class – as always, choose your own adventure.


If he says no, you breezily say “Okay! I’ll see you around,” and get out of there. The timing could not be better – it’s close to the end of the semester, so you’ll have a few more weeks of awkwardly running into him and then a whole month or so for everyone to revert to the time before you dared disturb the universe.

If he says yes, you will possibly find yourself in a sexy adventure. Or you can start nervously torturing yourself with pre-date jitters. Up to you.

Either way you earn the “Finally Asking A Cute Person Out” badge (Intern Paul – we’re going to need another badge).  Walk a little taller.  You are now a woman who asks out sexy men that you like.  You don’t need a makeover.  You, my friend, do not give a fuck.

If you want to cut your hair?  Cut your hair.  If being at college has opened your eyes to some cute fashion ideas?  Awesome – experiment with your own personal style. If you want to put on a flattering outfit in a pretty color on the days you have class with this guy because this crush puts a little sparkle in your eye?  That’s what crushes are for, even the unrequited ones – they make you wake up and feel alive. You’re not ruining Feminism.

But you don’t need to do any of that to be worthy of this guy or any other guy, and your letter stank to high heaven of the Hollywood-Beauty Magazine-Advertising-Sexism Industrial Complex message that has been playing on every single channel of every single medium since before we were born:  “You are not good enough, but you can be, if you hate yourself enough and buy enough things.” At least Procrustes had the guts to chop off your legs himself instead of using psychological warfare to torture you into doing it for him.

It’s totally understandable that you would fall into this trap because it’s so pervasive and automatic that it’s not something you can really outrun or outsmart even if you know what to watch out for. As soon as you get a healthy level of self-esteem some advertisement or TV show or anonymous Internet asshole will try to pull you back down, and you’ll watch the billionth narrative about how women don’t ask men out, they make themselves pretty so that they will be special and chosen or the billionth discussion of whether a powerful female leader has “cankles” just to remind you of where your place is and how you should lie down in it.  To like yourself fine as you are can be a radical, powerful act. I recommend it highly.

You’re worthy if you think you are worthy.  He may not like you back (even if you did undergo a transformation), but that’s not about your worthiness, that’s about his preference and agency because he is a separate person from you and you can’t know or control what’s going on in his head. Maybe your research as to his “type” was exactly correct and he only likes that one type of girl. Whatever! I only like people who are as least as intelligent as me and who have a little bit of sexy arrogance around it.  Give me someone who is brilliantly competent at something (and knows it) and I’ll give you one ladyboner. You have “types” too.

Here’s the story I’d like to write for you:

Hopeless Nerd is cool, and smart, and nice, and she likes a guy in her class, so she asks him out because she is confident and sexy as hell.  He says yes or no, and then some other stuff happens.

No makeover required.

56 thoughts on “Question #144: I am tempted to get a makeover so I can ask out my crush.

  1. hey, nothing is wrong with having a type. also? nothing says that people won’t date out of their type. i’m kinda into tall curly haired boys with glasses who read a lot and watch foreign films. so, naturally, i’d end up with a shorter, black dude from the mountains, right? yeah, well, these things happen.

    so, the ex-girlfriend trail…they are all EX-girlfriends. just sayin’…

    1. Purely observational evidence about someone’s “type” — especially if we’re talking physical type — is highly untrustworthy. Empirical evidence would suggest that my “type” is limited to round, white brunettes with glasses. But I could point you to plenty of blondes, skinny ladies, and women of color who I think are way hot. (Even the glasses thing is negotiable.) If you’re into someone, don’t torture yourself over whether you’re their “type” — just ask them out or decide to forget the whole thing and move on.

      1. Yup, I wanted to mention this! Also LW please don’t assume the ex-gf you know represents this dude’s “type” and start biting her style, that would just be too awkward for words >:|

    2. Did I ever tell you about the time my ex-boyfriend showed up at my birthday party with basically my Doppelganger?

      Reader, he married her. And she is fantastic and I love her and I love them together. But that was a weird, weird night.

      1. Jane Eyre! Yay!

        Yeah, I’ll bet that was. Glad you like your Doppelganger, I had this one girl decide she hated me because we looked a lot alike and had the same interests and her secret crush asked me on a date. It begged the question, “What? I should apologize for existing, now?” It was also a shame because aside from her unrelenting pettiness we totally could have been BFFs.

      2. At a place I used to work, we called that the “Ross/Russ” phenomenon. It happens more often than you’d believe it seems.

  2. “I just don’t think he’s into me”? He’s not. I think that if Hopeless Nerd were a guy crushing on a girl, it would be an obvious case of creepy For God’s Sake Leave Her Alone.

    “[Ex] comes swooping in…”? Maybe she’s not really his ex; this sounds like one of those annoying relationships where they keep breaking up and getting back together. This is probably why he keeps letting it happen; or it’s possibly because (see first line above).

    1. I think the difference is that when the LW says “I just don’t think he’s into me,” she’s basing that on his perceived type rather than his actions.

      1. If it is true that he’s not remotely interested and is trying to shrug her off (which doesn’t sound the case given the LW’s description, but is possible: I suspect a lot of us awkward geeks both fail to pick up on others’ social signals and are bad at hiding our own feelings) then it’s best that she openly ask him out, so he can refuse gracefully and they both know where they stand. Asking once and pleasantly isn’t creepy – not asking can verge on creepy depending on circumstances, but to be truly creepy takes asking and then ignoring the answer.

        So yes, LW, ask! Even in the worst-case scenario asknig makes things better.

    2. I don’t think I agree. The thing is, it’s true: people can’t always tell that you’re interested, and people don’t always approach attractive people who seem uninterested. They’re both fairly young and she seems shy.

      Creepy Guy is someone who has been trained to ignore social signals: someone who is in a situation that is not really ambiguous, but who has decided to treat it differently. It’s not, “Woman seems oblivious–must reveal my love!” it’s more, “Woman seems uncomfortable–must try harder!” And there is some overlap with signals and body language and other potentially subtle things, but not that much.

      It does sometimes happen that men are all, “LOVE!” and women are all, “THE HELL?” and men are all, “But I thought maybe you thought–?” and women are all, “FOR THE LOVE OF GOD, WHY? WHY DID YOU THINK THAT? WHAT DID I DO TO MAKE YOU THINK THAT? WHAT?” but that’s just one subset of a broader cultural insistence that men read assent into silence. That they don’t ask up front, and then don’t listen to the answer when it comes. And if the guy takes the rejection in stride and backs off, he’s not Creepy, just Incorrect.

      So I think she should go ahead and take Captain Awkward’s advice, ask him out, and if he says no thanks move on to some other nice young man. That’s not Creepy, either. It’s Enterprising.

    3. It’s not creepy to ask someone out. It’s creepy to perform a weird Vertigo-like makeover on yourself where you try to transform into someone’s dream girl but never speak up about it and hope that he’ll magically fall in love with you.

  3. The Captain is exactly right. Imagine the worst possible thing that could happen, which is this: you manage to totally make yourself over to be what you perceive his ideal woman to be. He falls head over heels in love with your construct, and you have to spend the rest of your days being someone you are not, until one day you snap in the middle of the night, and smother him with a pillow. No one wants that. Particularly not the pillow- it did nothing wrong.

    Neither you, who should be the best, most you you that you can be, nor he- he’s either into you, as you, or he’s not. There is, however, a way to find out. Ask him out. As you.

    1. Poor pillow, encased in plastic and shoved into a dark evidence locker until it is finally purged and incinerated; never again to feel the caress of soft tresses or to be lovingly, joyfully flipped to the cool side during a long summer’s nap.


  4. “I just don’t think he’s into me”? He’s not. I think that if Hopeless Nerd were a guy crushing on a girl, it would be an obvious case of creepy For God’s Sake Leave Her Alone.

    This is possible. Though I don’t know how just crushing on dude secretly, without even ever having asked him out, puts her all the way in creepy territory. We don’t know any better than the LW does where he’s at. So as the Captain said, she gives him one ping–one ping only, Vasily–to determine his position w/r/t getting a drink or a coffee or something with her. Either way, she’ll come away with evidence rather than speculation: If he turns her down flat, she knows she is a person who asks out men she likes, and now knows there will be nothing with this one. If he accepts the invitation, she knows she’s a person who asks out men she likes, and has scored a date out of it. If the date then goes nowhere, the LW still knows there will be other dates, as she is totally a person who will ask a fella out if she likes him. It beats drifting around in the dark, wondering if what sounds like tectonic activity could really be the Caterpillar Engine of Blossoming Romance.

    1. I’ll second that, being rejected (if that’s what happens) will make it waaaaaay easier to get over him because finally you know.

      On another note, if we’re the Awkward Army, shouldn’t we have medals?

  5. Just to jump the gun a bit, when you ask him out don’t use the word “sometime.” I used to do that all the time with crushes and they’d say yes and then I’d realize suddenly fifteen minutes later that I had to fucking ask them out again.

    Set a date.

  6. Aside from the fact that needing to change yourself for a guy is a clear sign that he’s not the right guy for you, here’s the thing about makeovers: men, in general, are not as stupid as romantic comedies make them out to be. If he did not want to be with you when you had long hair and wore jeans, he is not going to suddenly realize he was in love with you all along because you chopped off all your hair and started wearing leather pants to class every day. By all means, put on your favorite outfit and some lip gloss when you ask him if he wants to get a drink sometime. Just don’t expect that you can pull a She’s All That staircase move that will make him magically begin chasing your affections.

    1. I really like this point! Because women get so screwed in cultural expectations and narrative, we forget that men get screwed, too–represented as simplistic doofus stereotypes instead of complicated individuals–who maybe aren’t solely focused on looks.

  7. May I delurk to tell a sad, sad story? When I was 20, there was a boy I worked with who was oh so dreamy. He was incredibly hip, tall, dark, and brooding, and he was the lead singer in a garage band (of course he was). I crushed HARD on this guy for the better part of a year, thinking the whole time it was a big secret. Turned out I wasn’t as subtle as I thought I was and everyone knew, but anyway. He had a type, and I wasn’t it. I finally got bold once I realized everyone knew I liked him anyway, and I succeeded in dating him for about a month, but he warned me from the beginning that he wasn’t looking for a relationship (read: he wasn’t looking for a relationship with me). It broke my heart when he called it off, and it came as no surprise at all when he immediately started dating another woman who was EXACTLY his type. They were together for several years.

    The moral of the story? More than a decade later, I can look back with compassion for younger me, drowning in lovesickness over this hottie, and also with the clear knowledge that while he was a great guy (and I was a great girl!), we were totally wrong for each other, and that’s perfectly OK.

    Ask the guy out! If he says yes, then awesome! Have fun! And if he says no? That’s cool, too. You’ll have plenty of time to find other great guys who adore you for you. They’re out there! Believe me, you’ll like them just as much as this one, and asking them out will be easier now that you’ve had some practice.

    1. I just want to say that I like this story because it ends with you giving a nod to the fact that “that while he was a great guy (and I was a great girl!), we were totally wrong for each other, and that’s perfectly OK.” Whenever a rejection happens it’s so easy to fall into the trap of thinking either that there’s something wrong with the rejecter for turning you down, or that there is something wrong with you (and trying to figure out if it’s something you can change and how).

      Sidenote: for a while I had some close friends who really, really enabled this kind of weird overthinking on my part, by armchair-DSMing gentlemen who’d rejected me (“He does have some other symptoms of depression…”), and in some cases also by listing reasons I might not be their type. (One lady friend told me I might be “too hot” for the guy I’d been mooning over, adding that she herself preferred to date less attractive people because they weren’t conceited. I didn’t really know what to do with that information than feel both flattered and terrible.) A little you-go-girl-what-the-hell’s-his-problem solidarity is fine, but we all tended to go way further than that. I don’t know if this stuff is familiar to anyone else, but these types of conversations were such a big part of my life for a while that I just look back and want to write a big old PSA to my past self and all her friends: People aren’t jerks just because they reject you (or your friends)! And getting rejected is not automatic evidence that you (or your friends) are horrible or too hot or not hot enough or too smart or not smart enough or otherwise in need of a massive self-improvement campaign!

      1. Well, you know, that’s the warm, rational glow of retrospect talking. At the time, what I actually did was lock myself in my room and record an entire album’s worth of depressing indie songs about heartbreak and rejection on the used four-track I’d bought from him and tried not to act too weird when I saw him at work. Rejection is never fun, but we grow and we learn, right?

  8. When you use your words, it encourages the potential love object to use his words back and then you know where you stand. For me, knowing where I stand trumps the grand potential for rejection.

    I do remember the first time I asked out a guy I didn’t know at all, though. I’d seen him in a student-written play, and I’m pretty sure he was younger than I was (undergrad to my grad student). But we weren’t likely to run into each other on a large university campus, so when I saw him at an open mic night, I went to talk to him. Told him I’d loved the production, and then asked him out. He politely turned me down. And then not 15 minutes later got up on stage with his girlfriend to sing.

    Sigh. It was SO awkward, but I knew I hadn’t passed up a chance there.

    And the Army needs epaulettes.

  9. If pretty is your armor, then go ahead and get a haircut and a new shirt! Whatever makes your throw your shoulders back and think, “Aw, yeah- hot stuff coming through!”

    Just don’t let it have anything to do with him. And if he says yes, I guarantee he would have done so regardless of whether you even HAVE hair, but sometimes feeling like you are looking fine can make you do things you might be too scared to do otherwise, like put yourself out there and maybe have someone say yes and maybe be rejected. Go and get it!

  10. Dear LW,

    The Captain is spot on, but because I’m an opinionated so-and-so I’m going to throw in my two cents. I hope you excuse me when I add to the answer to your question with a load of questions for you to ask yourself:

    1. Let’s say you do the makeover. Will that give you the confidence to ask him out?
    2. He asks you out post makeover. YAY. You date, fall in love and stay together forever and ever. Is this new look comfortable? Is it something you wish to maintain forever and ever?
    3. If it wasn’t for your perceived ideas about his ‘type’ would you have ever thought about experimenting with this style?
    4. Try on a few sample of this new style – do not buy – do you feel like you’re playing dress-up, or do you feel like ‘you’?
    5. You have your first fight as a couple. Insecurities abound. Are you sure that you would never throw “well you only asked me out because I turned myself inside out and changed my appearance for you” at him?
    6. Are you sure you will never even think that he asked you out just because of what you wear and not who fabulous you really is?

    If you answered no to any of these questions, then that’s your answer. NO MAKEOVER.

    If however you’re feeling a little uninspired in the fashion/hairstyle department, think about what you find hot on you – not what you think a guy or this guy finds hot on you – and makeover accordingly. Putting on a new outfit, cutting your hair and experimenting with make-up does not make you a bad feminist. Nothing you do to yourself will make you a bad feminist, but some stuff you do may not be good for your own self-esteem and feelings of self-worth.

    So get a good night’s sleep, have a shower, put on something that you’ve always felt good in and ask that hottie out. Who knows, maybe his type is ‘girls with confidence who come striding up with their heads held high and ask me out’.

  11. I have to admit, it’s pretty hard to not be “into” someone if they aren’t your “type” IF you are the sort of person who must abide by your “self-set standards”. I myself have a pretty specific “type” I am attracted to and it’s a rare, likely non-existent, one to find in my dominant social circle; however, in some of my alternate social circles, there’s a decent number of them so I’m not terribly lonely or desperate.

    I’ve had a good handful of people who are definitely not my “type” ask me out, I’ve even gone out with a few of them (due to peer pressure and other factors like not knowing it was a date!). In the end, I seriously wished I hadn’t because it ended up being an ugly mess where they thought they were “THE Special ONE”. Why? Because they thought that they were awesome enough to change my standards! In the end, I got angry because they weren’t clear enough that they wanted to date me, and they got angry because I was still obviously looking at other people who fit my standards. Breaking the news to them that our “date” wasn’t actually a date was absolutely horrible for all parties involved.

    The point of me sharing this is to say that I feel people as a whole should not be pressured to date outside of their standards. And also, NO ONE should have to change any part of themselves to get a date! If person-of-interest can’t take the package as it is, he/she probably won’t be compatible with it in the long run. Now, if someone felt like changing simply because he/she wanted to, that’s fine. I’ve been through enough “image” changes myself just because I felt like it; it’s never been for anyone else but me.

  12. I agree with everything that’s been said. But I want to note that easy as it is to /say/ “once I know it’ll be better,” and it’s true, that sort of sentiment can be very difficult to believe.

    Here’s a line of thought that helps me believe it.

    What I want is some sort of silver bullet: a way to magically find out about what the other person thinks while leaving no trail.

    The thing about silver bullets is, they exist, but once they’re discovered they become ubiquitous almost instantly. Penicillin? Silver bullet of bacteria, so it’s in every drug store. Saline? Silver bullet of dehydration, so bags of it are anywhere medicine gets done. Lightbulb? Silver bullet of darkness, and also there is one within ten feet of you. Bullets? Silver bullets of not shooting things, and also used in every war and action movie.

    If there were a technique, no matter how complex, difficult, obscure it was, that solved a problem as large as secretly diving accurate knowledge of a romantic prospect’s feelings, it would be universally known.

    So no, there isn’t any middle way to squeeze through. If it existed, everyone would be there already.

  13. My honest, honest opinion is that he will reject you and you should ask him out anyway. You should do this so he can stomp all over your admiration for him and kill it dead, leaving you free. Like what you like! Be who you are! There is no pot so bent you can’t find a lid to fit.

  14. I am so glad you pointed out, Captain, the pressure that the media is putting on women– every day of our lives, hundreds of times a day– to be beautiful. We are told in so many ways that if we just buy this, or do our hair this way, or get rid of this feature we have, that we’ll be acceptable, loveable, even admirable. It truly makes me sick to think of young women feeling that they have to look a certain way to get attention from the people they find attractive.

    On the other hand, totally agree that getting a great haircut– one that makes you feel sassy and fabulous– and maybe even purchasing garments which YOU find appealing and feel you look great in just because you are you, not because you need to pretty yourself up to find a mate.

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