Help Flirting With A Guy

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So I’ve been messaging this guy from school that I used to have a crush on and now he is even hotter and I want to shoot my shot, problem is, I don’t know if he is gay or not. Can I get some help?
 
So I’ve been messaging this guy from school that I used to have a crush on and now he is even hotter and I want to shoot my shot, problem is, I don’t know if he is gay or not. Can I get some help?
What have you been messaging him about? Does he know you‘re gay? Has he been acting flirtatiou?
 
What have you been messaging him about? Does he know you‘re gay? Has he been acting flirtatiou?
He knows I’m gay and we’ve just been talking about random things
 
He knows I’m gay and we’ve just been talking about random things

do you THINK he’s gay?

there are so many opportunities I missed when I was single. That my opinion is SHOOT YOUR SHOT.

You’ll regret the not knowing more than a rejection.

he knows your gay…. So he shouldn’t be offended and stop talking to you just because you’re flirting. He won’t be shocked you’re into him even if he isn’t gay.

I say you have MORE to lose by NOT flirting
 
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do you THINK he’s gay?

there are so many opportunities I missed when I was single. That my opinion is SHOOT YOUR SHOT.

You’ll regret the not knowing more than a rejection.

he knows your gay…. So he shouldn’t be offended and stop talking to you just because you’re flirting. He won’t be shocked you’re into him even if he isn’t gay.

I say you have MORE to lose by NOT flirting
I guess I’ll try then
 
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I like to be straightforward with room to wiggle lol. I would say something like this.

"Okay, bare with me. This is going to be slightly awkward/embarassing but it all falls on me haha. I just have a confession that i've always wanted to tell you. Ever since I met you in school, gotten to know you, you instantly became a long term crush of mine. I know it may sound silly but you honestly made my school year great by just being yourself and getting to see you on a daily basis. I hope I get to meet someone out there just like you but you know, gay and well, feelings reciprocated haha".

Now the ball is in his court. I don't have to ask him his sexuality nor have him feel pressured into telling me. If he wants to pursue anything he can bring it up, if not then we can stay friends. If he has a problem with another guy having a crush on him then he's really not good for you haha. I just don't know the extent of your relationship with him as a friend to help with any other scenarios.

Hope it goes well! Don't forget to just be yourself!