How do I know I can tell a specific friend that I'm gay?
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So I'm way late to the party with answering your question, but here's my opinion. Nobody ever knows for sure whether they can tell a specific person they're gay, because everyone has a unique reaction to the news. It could be good, could be bad, could be "Don't give a fuck", could be "I know". I say if you don't want to hide it, just tell them.
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just tell him
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I would not tell if it is not necessary.
Friends, family, maybe colleagues, … I will say -
In my country, girls acpt more than guys
don't know how it is out there
but it can be a tip…check my public acts tumblr: aroundthere-vids.tumblr.com 
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Trynna use aleatory gay guys example to discuss wit him about dat! If u feel he's not friendly just don't tell! u don't have to tell anyone about your sexuality
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I never told anyone, but I'm not hiding in the closet. If they are close enough, they will know by themselves. If they don't know about me, it means they are not close enough. This topic is sensitive in some community so I don't expect to get into the awkward situation.
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If you scare, then do not tell them
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Maybe try and figure out what their general understanding and opinion about gay people is…
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I know this thread is pretty old, but it's been very interesting to read the responses. I hope the OP found the answer he was looking for.
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One thing I have learned is that straight guys can actually tell when someone has a crush on them… But it would be good to know about his feelings on the subject. But don't tell him that you like him... the end result WILL BE BAD.
