I can’t tell you how many times I’ve had minor crushes on guys I didn’t know were gay or straight. Nearly every time, I chicken out and fail to rake up the courage to hit him up. These kinds of situations are tricky because a) it’s basically all up to you, and b) you never know how to begin. In my personal experience, it begins with a connection.
The connection comes first before anything else. All the rest comes after a short (or long) series of conversation. Sometimes it’s easy, but other times it’s not. The one thing you always should do is to keep your pace. Here are a few tricks that help me:
#1) Make it clear that you, in fact, are gay. You’d be surprised what happens as soon as you make it clear that you’re gay. There is a lot to reveal from a person whenever it’s clear they’re talking to a gay guy. They’ll either become more comfortable or a bit intrigued – whether it’s an intimate or curious kind of intrigue is up to you to interpret.
#2) Invite yourself to sit next to him. Initiate the conversation first until you’re sure it’s worth moving forward. You never want to come off as flirting at the beginning because he might be straight and it’s always going to be an awkward feeling for him if that’s the case. So, go with the flow and become an aggressor. If you’re at a coffee shop or bar, sit next to him. If you’re at a party, ask him if he wants a drink (then go get it yourself). Do nice things for him and he’ll soon grow more comfortable to open himself up.
#3) Small talk first. Don’t jump the gun and start to sex-investigate him right off the bat by asking questions related to sexual positions or roles (yes, it happens more often than you think). Pretend like you’re talking to your future best friend – this always lets off some serious anxiety for yourself at the beginning.
#4) Ask HIM to recommend places to go to. This sets him up to nonchalantly ask you instead: “Oh, there’s a bunch of cool places you can check out around here. My favorite is ____, _____, or _____.” “Oh really? Where are they?” “Just near downtown area. I can show you sometime if you like.” “Oh yes, I would love that…”
#5) Invite him to a social, yet intimate, get-together. The beach is always a great place to invite him to because it’s public, but intimate at the same time because you will see each other shirtless (that’s always a plus). It’s a great way of creating an atmosphere that’s personal without it being awkward. Places like the movies, hiking, even bowling (public, yet private), are great ideas too. When there are people around, it’s going to inspire activity. But at the same time, you don’t want to lose your personal time.
#6) Make an effort to pop his space a little. Not in a creepy way, but in a manner that shows how interested you are. The trick is to lightly pop his bubble without actually entering it (let him do that). Studies have shown light touching, whispering in each others ear, and laughing while making eye contact unconsciously brings people closer to you. Work it to your advantage.
#7) Start the fun, then casually invite him on it. Find what your strength is, i.e. joke telling, magic tricks, board games, political debates, dancing, etc., then find a moment to do it. After a few minutes, point him out from the crowd and have a bit of fun with him. Who doesn’t like to be a part of a cool magic trick? Make sure he feels like whatever it is you’re doing, you’re doing it for him alone. He’s your audience. Make him feel important and who knows. Eventually he’ll open himself up to it. Once that happens, you have wiggle room to ask him out.
Let me explain a bit of caution for you. I know how easy it might be to get your hopes up, but in cases where you don’t know the person’s orientation, you have to enter it with no expectations. Have fun and loosen yourself up first, but never throw all your eggs in one basket.
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