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How to approach a cute guy.
#11
Usually alcohol helps... takes away some inhibitions.

Back in my single days... I was sitting at the bar at a Gino's East Pizza place in the Chicago area hitting on really cute guy who turned out to be straight. I think my opening line was - please don't be offended - but you are cute as hell! While he didn't run away he ultimately turned me down.

As far as random encounters - walking through the mall, you need to make eye contact, look them up and down, (if your really bold - wink), then as they pass, turn quickly to see if they also turn to check you out. If they turn to check you out, chase after them and introduce yourself.

Usually that's pretty obvious...

I find (for the lack of a better term) flamboyant personalities are sometimes better at meeting people on the street. Me, I'm very masculine or straight acting. If you talk to me you'd wouldn't guess I'm gay unless I told you. My partner on the other hand, I think you can tell just by talking to him.

At a gay bar / club / event - it's much easier. One more story then I'll shut up.

Went to Chicago's Gay Pride with a bunch of friends. One friend owned a Limo company so we parked out in the burbs then took the Limo into Boys Town. We watched the parade then hit the Bars. Roscoe's on Roscoe & Halsted is one of my favorite bars. Anywho, our whole gang went in there to drink and dance. Well somehow I hooked up with a guy from out of town checking out Grad Schools in the area. He had a hotel and he wanted to get out of there.

Once again - I think I used the same line - Damn you're cute, want a drink? Want to dance? Want to go back to your house or mine?

My friends were a little shocked, when I said that I was leaving and would catch a ride back to the burbs while holding this boy's hand as we left.
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#12
Offhand...

Mall, can't say. Clubs/bars, ask him what the good drinks (or whatever) are. At a gym, maybe you could ask him (or offer to) spot, if it can be done casually (note that some gyms only allow staff to spot), but from what I picked up it would be a very bad idea to say much of anything to a guy in the sauna (they talk a lot in TV shows, and also a homemade sauna I used to go to, but men and women both seem to spook easily if someone is too talkative, generally speaking, and the gyms I went to all have STRICT "sexual harassment" policies that you shouldn't violate). Museums, comment on something there beside him and see if he continues it. These all give him a chance to say something and an exchange can begin...assuming he isn't terribly shy, of course.

He might not be in the mood to talk to anyone. I wouldn't take it personally. Maybe he's having a bad day, he's thinking about something he needs to figure out and doesn't want to be distracted (yet), or he's expecting someone. So if it fizzles out or he's even rude about, then shrug. Who knows, maybe next time he sees you he'll be in a better or more social mood (might even feel bad about the last time) and be the one to start talking to you instead.

But unless you have good reason to think he's into men that way, I wouldn't come on too strong, just keep it casual and feel out the waters. Think of him as a potential friend, or at least as someone who deserves to be treated respectfully (and respecting his boundaries), it can help avoid the creepy vibe some men give off that can be uncomfortable (even if they're into men). Don't cling or demand a lot of time at first as that's also a red flag that can make people run. Also, if he's reading, then he'll probably be irritated if you interrupt him, even just to ask what he's reading.

If I were shy and awkward who wanted to meet guys, I'd go to a meetup or join some club (conventions might work as well) that focused on an interest or hobby of mine. That way, there would be plenty to talk about and people would generally be expected to talk. It should be easy to gravitate to potentials there. Even if nothing panned out, it might later, and in the meantime I'd work on my conversation skills and try to overcome my shyness, probably making new friends in the process (and who knows, maybe when they learned I was looking for a guy then they might know someone...'course that has it's own risks).
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