Closeted gay & need help dating

Each Wednesday, I answer one of your burning questions on the blog. This week Closeted Gay Guy That Can’t Even asks:

Let’s get down to business, Doc. I’m gay and not out, but every asks if I’m gay CONSTANTLY. I’m a virgin. A senior in high school. And I am an ArmyBrat, meaning that I move around every few years.

The school I currently go to has a little over 300 people and I don’t know shit when it comes to dating. I haven’t dated in a while (obviously) and am having trouble with even approaching any crushes. I’m insecure about every possible thing when it comes to dating that I don’t even know. What could I try doing to help boost my confidence and dating?

I feel this so hard. I was miserable at dating and approaching my crushes in high school and college. I felt so insecure and so unwanted and bumbling. I was terrified of rejection and so I never directly asked for what I wanted, which left me perpetually disappointed.

I hope you’re strapped in and ready, because I have a LOT of thoughts on this. And it’s not going to be a how-to list of tips on asking someone out. But then, you wouldn’t expect that from verbose me. Here we go.

The fact that you listen to the show and wrote in with your question puts you lightyears ahead of many of your peers. So many people go into their adult years having next to no information about sex and how to talk about it, and you’re already learning and thinking about things most people haven’t.

Let’s talk about the fact that you’re closeted and identify as gay first, then we’ll talk about dating and confidence second.

Other people asking if you’re gay is, frankly, none of their business. Sure, folks are certainly welcome to be curious about you, but you don’t need to answer or come out until you feel like it’s safe and you feel ready. If coming out means potential bullying or a tough living situation with your folks, you don’t have to come out yet. Your safety needs to come first.

Which brings me to support.

As a young gay person, having support is a crucial part of feeling less alone.

From supportive parents or family members to Gay-Straight Alliances at your school to local sexual health centers, I highly encourage you to seek out some peers and groups who can understand exactly what you’re going through.

There are some super rad online forums and resources, too.

Scarleteen is amazing. Between their articles, their resources, and their forums, you will find no shortage of folks going through the same things as you. Be sure to check out the resources on the right-hand side of the page, too. There’s even a support line where you can text questions to a hotline staffed by queer teens!

The Planned Parenthood in Toronto has a sexual health initiative that was created by teens for teens and has ton of great resources on sexual identity, gay sex, and relationships. Check it out at

Having queer friends can be such a beautiful way to start having some of these conversations in a super safe space. Plus, as you get to know folks, you might meet some people who you want to crush on, too.

Speaking of conversations, getting clear on what you want and what you mean when you say things like “virgin” can go a long way in building your confidence.

For instance, when it comes to being a virgin, what do you mean by that exactly? What does sex mean when you say “I’m having sex with someone?” Will you no longer be a virgin if you give someone a blowjob? A hand job? If someone puts a finger in your ass? If you both are naked and touching but no penetration happens? (In my book, all of that is sex, but your book might look a little different.)

It might seem weird, but the clearer you get on your own experiences and terms, the more confident you’ll be communicating that to someone else when the time comes.

Autostraddle has one of the most incredible resources I’ve ever seen about talking to a partner about relationships and sex. I cannot stress enough how valuable it is for you to go through these questions if you want to feel empowered and confident about your needs and experiences.

Your future partners will thank you. Trust me. This stuff is so important.

Journaling your thoughts and feelings can be another powerful way to start finding your own truth. Write about what being gay means to you. Take the time to really put words to how YOU experience gay right now (I say right now because you may find the way you experience your sexuality changes over the years).

All of this brings me to the nitty gritty of dating. As you start getting really clear on your definitions, your experiences, your wants and needs, you will be positioning yourself to be a heck of a lot clearer on what you want and don’t want in a partner.

But so much of dating and sex is about actually trying stuff and figuring out what does and doesn’t work for you. Maybe you think you like a certain kind of sex because the fantasy is hot as hell but then when you actually try it, it’s not what you thought it would be.

It’s difficult to know what personality traits in a partner will drive you up the wall until you actually experience them and realize, nope…I just can’t.

Rejection, mistakes, regret, and being endlessly awkward is normal and it’s a part of life. Whether you’re 18, 38, or 80, dating and sex are always kind of tense or strange or uncomfortable.

People who are good at dating have simply done the work to have resilience and tolerance for those feelings.

Reid Mihalko likes to talk about embracing the awkward. It’s not about eliminating it, but instead just accepting that feeling awkward is normal and if you feel awkward, then you’re probably doing something right — like being vulnerable and taking a risk.

If there’s one thing I want to impart on you, Closeted, it’s this: rejection is normal and it’s not personal.

So, give yourself permission to get rejected. It’s OK to feel hurt or disappointed by it, but know that there are endless opportunities behind each and every rejection. In the moment, it might not feel like that’s true — especially if you’re at a really small high school — but take it from me, there are always new people, new feelings, new desires waiting to come to life.

The more you realize who you are and what you bring to the table in your own unique way, the more confident you’ll be. That’s why having a strong support network and having a really clear idea of who you are is critical.

You’ll also be much less likely to make poor choices — like falling in love with the straight guy in your math class or hooking up with someone on Grindr just to get the experience behind you even though it’s not what you really want.

Instead, by sitting down and mapping out your world and your hopes and desires, you can make much more informed decisions.

And that is one of the most attractive things you can offer in the world. People are drawn to folks who know what they want and can articulate it in a confident way.

Give yourself permission to do some of that work now, surround yourself with badass queer friends, and you’ll be surprised at how the rest starts coming together on its own.

What was dating like for you, dear reader, when you were in high school and college? Did it come easy for you or were you as awkward and invisible as me? Comment below and let us know.

Have your own question about sex, relationships, kink, or your body? Send it my way (there’s an anonymous option) and I may answer your inquiry on the podcast or in the weekly advice column, Wednesday Words. Post originally appeared on

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