The Hook Up: Insecurities of the inexperienced and best friend crushes

I’m a 16-year-old queer female. I’m comfortable with my sexuality and am out to most of my friends. The problem is I’ve never dated either a guy or a girl and feel like I’m getting on a bit in terms of having my first romantic experience. I spent a lot of time putting my lack of dating down to not being comfortable with my sexuality but now that I am I feel like I’m running out of excuses. There are no (openly) gay girls at my school and I don’t socialize much with people outside of school. Yet even when I do I never seem to meet any girls interested in more than a drunken kiss.

I guess I’d like to meet some queer-identified girls but without going to anything as direct as a gay-youth group (mainly because this would be difficult to explain to my family, whom I am not out to). I’m worried that if I reach 18 and leave school without having ever had a relationship this will completely destroy both my confidence and weird out anybody I might meet in the future. Help for a lonely teenager?

Anna says: Dang, girl. If 16 is “getting on” then I am so over the hill that the hill looks like a shoulder pad on one of Bette Porter’s power suits. You are just a baby, darlin’! And I don’t mean that in a condescending way. You have so much of your life ahead of you, including all kinds of romantic experiences, delightful and horrific and sweet and meh.

Tina Fey didn’t lose her virginity until she was 24. Lisa Kudrow was 31. Matthew Morrison (aka Mr. Schuester on Glee) was 21. Ian McKellan (aka Gandalf the Gay, I mean, Great!) was 22. This is just a very small sample of people who didn’t have much or any sexual experience until they were in their 20s.

There are SO MANY 16 year olds who don’t have any romantic or sexual experience. I barely did at 16, and I can tell you that the experience I did have was pretty terrible because teenage boys aren’t well trained in the erotic arts, to put it delicately. I know that magazines and TV shows make it seem like all teenagers are getting it on like crazy, but that’s just not true. I mean, some of them are, probably the ones who are really vocal about saving themselves for Jesus. But plenty of teens are also simply sitting around watching Food Network and dreaming of the day someone will lovingly whip up a souffle for them (which has been my fantasy since the late ‘90s).

Not having a romantic partner by a certain age doesn’t make you any less of a person. It certainly doesn’t make you a weirdo or social pariah. What’s crazy is the belief that when you hit some magical age milestone (for you, it’s 18), that you will be deemed unlovable or unworthy or that your “confidence will shatter.” That is banana sandwiches, my friend! You will be SO loved, I promise. And sexual experience doesn’t equal desirability, or even confidence. Confidence comes from within, not from what goes in you, to put it not so delicately.

In terms of finding romantic partners who are queer and are teenagers who live near you and whom you can meet without joining your local gay-straight alliance (or equivalent), that’s a bit trickier. As you probably noticed, not many gay teens are out, for a variety of reasons. Sometimes they have unsupportive families, sometimes the social pressure to be straight is too strong (or the whole not-wanting-to-get-beat-up problem), sometimes they simply haven’t realized they’re gay — I was one of those. Didn’t get a clue until I was almost 21. And you know what? When I finally did figure it out, no one refused to date me for my lack of girl experience. It wasn’t an issue because I didn’t allow it to be one. I didn’t let other people provide the timeline for my love life, and neither should you.

But I will say that finding potential dates is similar to finding potential friends. It helps to go about it with intention, since odds are low that we’re going to bump into our soul mates while taking out the trash. To that end, meet as many people as you can. Meet and befriend people outside of your usual circle (as long as you click). Join clubs that interest you at school. If there aren’t any, then start your own.

The most important thing — far more than learning to unhook someone’s bra with your teeth — is to learn how to be comfortable with yourself, and to build a fulfilling life, one that’s free of silly deadlines or beliefs about yourself that aren’t true. You are awesome — I can tell by how much self-awareness you already possess — and you’re going to have an awesome love life, when the time is right.

I have been in love with my best friend for two-and-a-half years. We cuddle A LOT and are very close. We have life plans together. I tried everything (and I mean EVERYTHING) to get over her when she was unavailable. When nothing that I did on my own worked, I tried really really hard to get a girlfriend because I thought that it would help to focus my romantic and sexual energy on someone who could reciprocate.

About two months ago a girl started flirting with me, and I didn’t know how to handle it because I have zero experience. I hung out with her and texted her a lot, and basically just clammed up whenever she hit on me. Right now she is out of town for a couple of months, so that is on hold (although when she gets drunk she still sends me suggestive text messages).

However, about a month ago my best friend came out to me. I keep hoping that something will happen between me and my best friend, but no matter how erotic some of our interactions seem to me, I am afraid she only sees me as a friend. And while I don’t think I could ever make a move, I pair myself romantically with my best friend in every imagined version of my future. However, if she is not into me in that way, I would like to have sex at some point, and I do really enjoy Flirtatious Girl’s company. I am just afraid that any romantic relationship I have will be tainted by my love for my best friend. I cannot get rid of it, and perhaps that is unfair to Flirtatious Girl. What should I do? — Hopeless

Anna says:If you want to know how your crush/best friend feels about you, then ask her. It’s as simple as that. Really. I know you’re worried about the cards not falling in your favor, but it’s clearly giving you a lot of anxiety not knowing. And it appears to be tainting your other romantic interests, a la Flirtatious Girl.

I’ma be frank with you, Hopeless. Sometimes getting a straight-up rejection from a crush is the best way to get over them. Sometimes we need our No. 1 Perfect Soul Mate In Our Mind to look us in the eye and say, “Nope, don’t want to see you naked actually.” It does wonders at providing that soul-crushing clarity we sometimes need to get our head out of the clouds and back in the water where it belongs (Wait, this isn’t The Little Mermaid). Not that I want you to be rejected; I don’t. I’m just saying, you’re driving yourself crazy wondering about this girl, and cuddling with her platonically, and daydreaming about your future together. Wouldn’t you rather know for sure if there’s any potential to be together and either live happily ever after or move on already? I sure would. Hell, I have anxiety just reading your letter.

You don’t have to “put a move” on your crush. All you have to do is be honest. “Hey Best Friend, I’ve been having less-than-friendly feelings about you. Should I knock it off or should we play naked Twister already?” But please, do say something. If you think this all over and decide that you absolutely can’t tell your friend about your Big Feelings and the matching grave plots you’ve already picked out, then you must do everything you possibly can to move on. That means no more cuddling. That means pursuing Flirtatious Girl with intention (or any other girl, really! I’m not picky). That means spending less time together so your heart has room for someone who can potentially meet your needs and make you happy. But really, I implore you to just come clean. We try so hard to avoid any and all unpleasantness in life, not realizing that the unpleasantness is as inevitable as death, taxes, and hangovers.

Rejection, the thing you fear so acutely, isn’t the end of the world. It simply means that one particular person at one particular time in your life wasn’t right for you. That’s all. The sooner you learn to confront it, the sooner it will be just another blip on your long, amazing love life (and it will be really long — 50-80 years probably). I hope your crush has Big Feelings for you too, but if she doesn’t, I know some other girl is just around the bend, waiting to share some of those sweet life plans you’ve dreamt up.

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