Dear Captain Awkward,

I am a twenty-five-year-old introverted, socially-awkward, geeky fat girl who has never been kissed. I feel weird about this, because it feels like there is something terribly wrong with me, and all of my friends are way more experienced than I am.

I don’t really know if I have the energy for a relationship right now, and have had terrible luck in dating — mostly I end up meeting guys who have fetishes for inexperience or fatness or smart ladies, and I am the only fat/virgin/geek girl they ever met, and they MUST HAVE ME or they will be ALONE FOREVER! and they tell me that clearly they are the only person who could ever like me anyway, and then I block them on AIM and don’t answer their calls. Or people who I am into are clearly not into me, and if they’re nice about it we end up as friends, and if they’re jerks about it I’m magically not into them anymore, because I’m not into jerks.

At any rate, sadness often causes me to whine to my friends about how awkward I am and nobody loves me except for creepy dudes, woe, angst. My friends are lovely, but usually they pull out the old story about how I’m just really intimidating, because I’m smart and funny and awesome, and CLEARLY dudes don’t ask me out/get weird and distant or jerky after I’ve asked them out because I am JUST TERRIFYINGLY AMAZING.



I think at this point I just need to get out more and Be Social, but I am asking if we can please get rid of telling women that they’re just too intimidating to be someone’s girlfriend? Firm in the belief that I was too intimidating to date, here is what I used to do on the few dates I got:

1. Not make jokes, because funny women are intimidating.

2. Not talk about my own interests, because women with hobbies are intimidating and also showoffy. Especially if their hobbies are things that require talent or lots of hard work! Women with talent or who work hard are especially intimidating.

3. Not have opinions, because opinions on women are *so gross,* amirite?

4. Ask the dude all about his interests, even if I didn’t find them interesting, because that made me less intimidating, and who cares about whether I’m having a good time on this date, right? It’s all about the guy.

5. Keep going on dates even after it was clear my heart and groin were not into this dude, because at least he wasn’t intimidated, and this might totally be my last chance at ever! finding! love!, because I am so intimidating!

Here’s the sad thing: being as bland and inoffensive as possible actually *worked* in the short run. And it would have worked for longer if I could have overridden lack of heart/groin and kissed any of the guys who I ended up doing this with. Just think — I missed out on so many passionless, boring relationships!

But I don’t want to date just ANY guy. I want to date a guy who is into the real me, and I want to date a guy who I’m into. Also, those dates were horrible and no fun, and thus I have avoided dating as much as possible for years.

So that’s my argument for losing the Intimidating Ladies Never Get Any trope. What do you think? Also, do you have any advice for a girl who went about dating All Wrong for years, and has finally learned to be herself on dates? I finally was myself on a date, we had fun, he just wants to be friends and I think I do too, but I’m worried about slipping into my bad bland habits next time I go out with someone new.

Also, is there any good way to answer questions like “What was your last relationship like? What do you mean you’ve never been in one? Why not?” I have a feeling questions like this are probably just too nosy for a first date and a sign that this guy is not for me, but maybe I’m wrong? It just feels too much like a job interview question.

–Intimidated By Dating

Welcome to the SECRET ORDER OF THE TERRIFYINGLY AMAZING, Letter Writer. I love you so hard right now, you don’t even know.

Looking at my own checkered past and the collection of mostly happily partnered 30-something Valkyries and awesome geeky dudes who surround me, I’m here to say:

There are smart, cool, heterosexual dudes who like fat girls, smart girls, introverts, talented, funny, sarcastic girls, geeks, sluts, virgins – all of it. You know what? They just LIKE WOMEN, period. They were raised by awesome Feminists and/or they’ve done some work on their own privilege and on understanding sexism and/or they’ve grown up in our time when men and women can be friends and it’s not a big deal (which is one of the things that makes this such a great time to be alive). They see us as people, and they laugh at our jokes and they root for our creative and professional successes and they tell us to piss off when we deserve it and we don’t have to make ourselves smaller to be with them. They like women.

And behind closed doors there are a lot of us who look like we rolled out of Hobbiton this morning to walk our hairy feet to second breakfast…who are having white-hot sex. The best kisser in the Midwest is a nocturnal (and therefore extremely pale) dude who owns so many books you’re kind of afraid they’re going to fall on you when you’re in his apartment, and introvert doesn’t even BEGIN to describe…ahem. I digress. Someone who acts like his manly attentions are like some kind of amazing favor because you are (fat)(geeky, which just means really passionate about things you like and is a GOOD quality)(smart)(a virgin)(too awesome) has internalized a lot of toxic bullshit about what is desirable in this culture, and you don’t want him getting any of that on you. Think of it as him speaking in code, and if you were to decipher that code it would say “I have no idea where the clitoris is.Have you read The Fountainhead? It’s my favorite book.” You are correct to banish That Guy whenever he pops up.

Some of we TERRIFYINGLY AWESOME folk go a long time on our own without a partner or between partners, and we learn how to be happy in our own company in between bouts of making ourselves vulnerable on the dating scene or moments of dumb luck. It doesn’t seem fair, like when you are riding the Brown Line at rush hour and it’s full of couples who stepped out of a De Beers ad fondling each other and you’re periodically blinded from the way their engagement rings catch the morning light. Then you overhear some of their conversations, like an intense 40 minute conversation about the best smoothie place or celebrity weddings or “good carbs vs. bad carbs” or “where should we get our teeth whitened before the wedding?” while the old Second City “Mainstream-Impaired Guy” sketch runs through your head. “I sold my boat and bought another boat!” “16 shots of Jaeger.” “Sports!” Maybe that’s just me?

I recently re-read The Rules (because I wanted to make fun of it here, and holy wow is it garbageterrible) and your list of stuff you’ve done to make yourself less…less funny, less interesting, overall less awesome…in order to have short-term “success” at dating at the expense of self-expression and self-worth and being accepted for who you are is right out of what they say you should do before you even start looking for love. Smooth off all your rough edges, ladies! Oh, and by the way, you’re going to have to maintain that bland, shellacked facade and act like a Bachelor contestant even after you’re married in order to “keep the spark alive,” because if your husband doesn’t feel like he is “chasing” you all the time it will kill his bonerz dead.

It’s literally in the book that “men don’t like sarcasm” and “men don’t like women who tell jokes” so you should never be sarcastic in front of them (sarcasm and jokes kill bonerz). If my goal in life was to marry some generic dude who wants a ladylike thin woman who is never sarcastic and who only asks him about his own hobbies and interests and is never competitive with him or funny, I would be SOL and the room around me would be littered with sad, deflated boners. Fortunately I want to marry someone* in the hilarious, awkward bear category, and I think he will be okay with what I’ve got going on here.

Listen, my young Padawan, you are doing everything exactly right, and to describe your awesomeness as somehow “intimidating” is a very…Rich from Marie Claire kind of move. You don’t need to slow down for other people, you need to find other people who can keep up with you. Every now and then a random online dating site dude will tell me “Wow your (sic) kindof (sic) intimidating” and I usually respond with “Wish I could say the same about you!” DELETE BLOCK REPEAT.

I think your instincts to be more social in general are correct. Go on more first dates. Find some regular activity that will bring you into contact with people more than once in a casual way where you can get to know them. Do your part to call out and take down sexism (and racism) in the Strong Successful Women Intimidate Men So They Will Die Alone (And It’s Their Fault) trope, like you did with your awesome rant. Do a little less crying on the shoulders of your friends where you wonder aloud what’s wrong with you and therefore invite them to try to invent something that could be wrong with you. Go forth and intimidate the bonerz off of people who see strength and confidence as intimidating, because you are TERRIFYINGLY AMAZING. You may wither bonerz of the unworthy with your steely gaze, but the good news is you will create desire in cool, fun, smart worthy men who actually like women.

Finally, in answer to your last question, that “What was your last relationship like?” question is so job interviewish – “Why did you leave your last position as Mike’s girlfriend, Jessica? Where do you see yourself in 5 years?” I can hear the hum of the Starbucks frappuccino blender behind it, so we’re already in deeply unsexy territory. It’s not a totally ridiculous thing to ask, but it’s not really for the first-ever conversation you have with someone either. I’d suggest answering honestly in a low-key way “I’ve gone on a lot of dates, but no real relationships so far” that indicates it is not a big deal or source of shame or discomfort for you, and then turn it back at him. If he is weirded out by that, it’s his issue, not yours.

Good talk everyone.

*2019 note: Initially listed as “Louis CK or a reasonable facsimile,” holy shit did THAT not age well.