9 Flirting Tips for Socially Awkward Gay Men

Nothing sucks more than being an awkward person in an outgoing world. From my experience, it’s like constantly taking a Pop Quiz without notice. The nerves come out and assumptions go in. Needless to say it’s a fall down mess.

But there are psychological and emotional tools everyone can benefit from. In the gay community, we have to use what we got. If we’re awkward we need to find ways to sift that into gold. Here are a few that can help:

#1) Never pretend.

You won’t get anywhere if you aren’t yourself. One of the biggest reasons we feel awkward is because we pressure ourselves to “act” like something else and we don’t know what to do about it. Inauthenticity is unfamiliar for us, and when we feel it coming like word vomit we jump into a shell.

We are enough, exactly as we are. Chill. Breathe. Smile. Relax. There’s no reason we need to put on a show for anyone. Admire the surroundings and allow yourself to have a normal conversation. If you feel awkward, use it and turn it into something funny. Be authentic in what you are and stay grounded to your personality and point of view. Be comfortable first, and awkwardness fades away.

#2) Have a drink (but don’t go overboard).

A drink for an awkward person is enough to let the screws loose a bit. It’s all about being comfortable with your surroundings and getting out of your own head. Look (and think) straight and linear, not peripherally or invisibly. All that exists is what’s in front of you.

Whatever you do, don’t have more than three strong drinks. This will have the opposite effect. It will make you overthink and become stimulated by your feelings that your personality reflects it. Let the alcohol do what it needs to do, no need to force it.

#3) Don’t depend on the kindness of friends.

In other words, don’t let flirting be a game of “Telephone” by telling your friend to tell his friend’s friend to tell his friend to tell him you think he’s cute. It’s not wrong necessarily to say, “He’s hot. What’s his name?” but you should never depend on it the whole night.

Practice the art of small talk. All it takes is observing him, your surroundings, maybe what he’s wearing or reading, and slide in from there: “I can’t believe you’re reading Harry Potter, I’m the King of Potter Trivia. I’m a Griffindor by the way.” “How do you know ______?” “I think ____’s dog has a crush on you.” “Nice shirt. You like the Rolling Stones?”

#4) Stop thinking he’s “too hot” for you.

Our biggest excuse not to approach a man is convincing ourselves he’s out of our league. Trust me, assumptions are your worst enemy. You’re not approaching him because you think he’s hotter than you. You refuse to do it because deep down you feel you don’t deserve him.

You do deserve him. You deserve anything you want so long as you believe it. There are countless of excuses we tell ourselves to not go through what we want to accomplish. We can talk our ears off most of the time, but at the end of the day we have to filter truth from the lies. And the truth is we hold ourselves back due to assumptions based on fiction.

#5) Is he worth approaching?

As an awkward person, you need to save your energy. It takes a lot to approach someone, so you shouldn’t do it willy nilly. It needs to be someone you know is worth it, a person you won’t regret approaching afterwards.

Don’t waste your time flirting with a guy because your friends pressure you to. Save energy and efforts for a man of your choosing. Flirting with a guy you don’t like is always going to be awkward, even for the most social among us. The last thing you want to do is traumatize yourself to the point of no return.

#6) Never self deprecate.

It’s easy to deprecate yourself in front of him because it’s easy access to comedy. Most comedians rip themselves to shreds, and it’s funny because we as an audience can relate. But when it comes to flirting, he needs to know that you respect yourself. If you respect yourself, you can respect him.

In a way, we train the world how to view us. If we tell the world we’re not good enough or we’re stupid, it’s only a matter of time before they rise up to meet us. Give him the first lesson.

#7) Know what you want.

When you know exactly what you want in and from a man, when you see someone close to it, the words magically appear. I don’t know how it happens, but it does. Use your emotional intelligence to dig deep and discover what it is you really want in a partner to decide your non-negotiables. This will make you feel more comfortable in situations because you’re grounded on foundational awareness.

#8) Play Cupid.

There’s nothing like right place, right time scenario to let love bubble. If you happen to be in the same restaurant at the same time, uh oh, what a coincidence (right?). If you’re in the same elevator at the same time in the morning, that’s merely fate (is it?). Use your noggin to think outside the box and play Cupid – take matters in your own hands, that way awkwardness will be in your control

#9) Know when to back away.

Don’t force something out of him that isn’t there. Be graceful when letting go of something that isn’t meant for you – never ignore the signs. Don’t be that desperate. If he isn’t into you, he isn’t into you. Move on.

On the same note, if he isn’t what you expected he was and you lose interest, back away slowly and be proud of yourself that tried. You can’t fake chemistry. If it isn’t there, it isn’t there. It’s not your fault.

David Artavia


David is an award-winning journalist and editor at The Advocate, Plus, and Chill magazines. His work also appears at Pride.com and OutTraveler. He lives in Los Angeles where he lives vicariously through his friends.

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