The Hook Up: How to Overcome Shyness

Let’s see if I can explain this right. There’s this girl. I’d consider her my best friend. She’s kind of been my everything lately. I think I’m falling in love with her and I think she’s made it pretty clear that she has feelings for me as well. I’d really like us to be together but I don’t know how to make that happen. I’m really shy and hesitant so I don’t know if I could just lay everything on the table. And since she knows I’m so shy, she doesn’t want to make me uncomfortable so I don’t know if she’d ever make the first move. But I’m really scared that if I don’t tell her how I really feel soon she’ll lose interest in me or find somebody else. I can’t lose her. What do you think I should do? — Shy

Anna says: It’s hard to be shy. I empathize. I used to be quite shy myself (and still am in a lot of ways). Without the aid of the Internet and Miller High Life, I don’t know how I would’ve gotten laid at all in the early aughts. But I will say that being scared of acting on one’s feelings is a pretty unreliable life strategy. It leaves you with a lot of questions. A lot of “what ifs” and regrets and really high bar tabs.

You have Big Feelings for this friend of yours. It’s OK to express them. Armageddon will not occur because you told one person you feel less than platonic about her. So yes, Shy, tell this girl you like her. Tell her in whatever way you feel comfortable. Ask her out on a date. Tell her what you told me: Regardless of what happens, you don’t want to lose her. Face-to-face is best because no matter what her answer is, y’all will probably need to process. In the worst case scenario, she’ll say she doesn’t reciprocate, things will be a little awkward for a few weeks, and then you’ll get over it. In the best case scenario, you’ll have a swell lady to mack on who also happens to be a great friend.

Don’t close yourself off to new, potentially awesome experiences because of fear. Fear is an asshole! Here’s a quick litmus test to give yourself whenever you’re unsure whether or not to forge ahead into unknown territory: Does the risk outweigh the potential outcome of awesomeness? If you thought, for instance, that being honest with your friend would cause serious damage to your friendship or that it would make her really uncomfortable, then the risk might not be worth it. But in your case, you know each other well, and her feelings are “pretty clear” for you. Your risk is minimal. All you have to do now is suck it up and let it out.

And you can totally do it. Take a deep breath, adopt a power pose for two minutes to boost your confidence and lower your stress, and get ‘er done. Then come back and tell us how it went. Internet cosmos and high fiving will commence regardless of the outcome.

I’ve always had zero gaydar and a thing for straight girls. to the point where it’s become a running joke in my friend circles that the best way to spot a straight girl is to see if I find the girl in question attractive. At the moment there’s this girl who I’ve been infatuated with for almost two years now. We’re at the same uni doing the same course, so I see her at least twice a week when school is on. I’ve been half in love with her since the second week of uni and thought my feelings would go away during the summer break but we’re back now and they’ve only gotten worse.

The problem is, despite the fact that she walks like a straighty, talks like a straighty and has her preference for men declared on Facebook like a straighty, there’s a little part of me that refuses to believe it. (I’m pretty sure it’s the same part of me that’s infatuated with her.) There’s is zero indication that she’s even slightly interested in girls but then we make eye contact or get to talking and I can’t shake the feeling that she’s not 100% straight and that she likes me, just a little. It’s a gut feeling, but my gut feeling has led me astray before. (And before you ask, I’m not good enough friends with her to just ask her about it outright.)

It occurred to me recently that I probably refuse to believe she’s straight because I’ve been there before with straight girls and it always ends with me being sad and heartbroken, and for once I just want to NOT be making the same straight girl mistakes over and over again. But acknowledging that hasn’t helped me get over her at all.

So I guess what I’m asking is, is there anyway I can quit my straight girl tendencies or at the very least is there a way I can stop obsessing over this girl? Help!

Anna says: I used to have a similar problem. Except not only were my crushes straight, they were also married to men. This became a humorous barometer by which I would measure someone’s sexual identity, much like your friends do to you. The trouble with having a straight girl crush is twofold: One is that you might be wrong about her straightness, since “looking straight” doesn’t mean that she is absolutely-never-even-wore-flannel-let-alone-looked-at-another-girl straight. It’s hard to tell where a person falls on the sexual spectrum from appearances alone, unless you’re relying on stereotypes, nametags, or very literal conversations. The second problem is that being attracted to women doesn’t mean that you’re ONLY attracted to queer women. Many queer girls fall for straight ones. Sometimes this works out, and sometimes it doesn’t.

That said, pursuing your particular crush doesn’t seem all that promising, given how little you know about her and the markers you described (identifying as straight on Facebook, for instance). It’s possible that your crush isn’t 100% straight–very few people are, after all — but how much time and effort are you willing to devote to figuring out how possibly not-straight she might be given the right situation/person/number of Smirnoff Ices consumed? You’ve already spent two years crushing on this girl. That’s a lot of time for not a lot in return. Is this girl preventing you from pursuing other potentially amazing girls who you are sure like what’s in your pants? If so, then abort immediately. It’s definitely not worth it.

However, I will say that you’re in school, so you’re probably in your early twenties, meaning now is the time when you should be pursuing people who are inappropriate/wrong for you so you can get it out of your system. Yay, learning things the hard way! I won’t be shocked if you do decide to endlessly speculate about this girl’s deep-rooted desires. If the mystery is really driving you crazy though, then devise a way to find out. I know you said you don’t know her well enough to outright ask, but it’s not THAT hard.

You don’t have to be all, “On a scale of 1 to 10, how much do you enjoy penis?” You can be subtler than that. Bring up a bisexual celebrity as a topic of conversation — Anna Paquin for instance, or everyone’s favorite mother of adopted African children, Angelina Jolie. Then ask her if she’s ever “experimented” or if she would. Talk about girls you like and see if your crush gets squeamish, or intrigued, or changes the subject. There was a while that I became obsessed with knowing about my co-workers’ pasts and would ask all kinds of nosy questions. No one ever refused to talk about it, except one girl who didn’t discuss sex at all, ever.

Again, I’m not saying you should pursue this girl. I’m exhausted for you just thinking about it, but if you’re hell bent on bending her over, then I won’t stop you from trying. But — shhh, you heard it here first — it’s probably a waste of time.

Hailing from the rough-and-tumble deserts of southern Arizona, where one doesn’t have to bother with such trivialities as “coats” or “daylight savings time,” Anna Pulley is a freelance writer living in San Francisco. Find her at and on Twitter @annapulley. Send her your Hook Up questions at