Hello everybody! I haven't been on EC is in a while, but I need some advice right now. You see, there's this guy that I've best friends with for a while now. He's one of the few people that I share similar interests with and we get along amazingly. A few months ago I started to have a romantic interest towards him, but I felt insecure and awkward so I didn't ask him out. Eventually he got a new girlfriend so I figured I had missed my opportunity until today when he broke up with her. I feel like I have a renewed chance now, but I don't know how to ask him out without being awkward. I don't even know when I should ask him out because right now he's depressed from breaking up with his girlfriend. If I ask him right now it's probably going to piss both of them off and ruin my chances, but if I wait too long then I fear he will find somebody else. If he does reject me then I'm afraid that will ruin our friendship. And of course I can't really match his girlfriend. While she can post hundreds of pictures and romantic statuses online to make the rest of us feel patheticly lonely, I'm still stuck in the closet thanks to my homophobic family so I can't even update my relationship status. I'm not very outgoing and flirty either like she is, and I feel like he might expect that. To sum it up, I really want this guy to be my boyfriend but I just don't know if the situation is good. I've never asked out anybody so I don't know what to do and I'm getting anxious.
Hey gaynerd64, Sorry to be a party-pooper, but do you have ANY reason to think he might be gay or even bi? IF he turns out to be bi or gay, you certainly don't want to be a rebound relationship. That would both probably not work out and ultimately ruin your friendship. From what you wrote he seems straight, but he also seems to be a valuable, good friend to you. If you need to resolve for yourself the reality that he either is or is not a bf prospect for you (even if he is gay or bi, you might not be some he likes 'that way' - and believe me, I've got a really great gay friend whom I love to death for his friendship, humor and personality, just not 'that way', even though he constantly makes it clear that he's always willing to 'hookup.' But reality rarely conforms to our fantasies (gay, bi, or straight). So, if he's a really good friend, if you Come Out to him and tell him that you have a crush on him you're taking a chance, BUT most guys these days - especially Millennials like you - are super open-minded and he would most likely just tell you that he's not interested in you 'that way.' Ultimately, though, it's your call. You know him. And only you can estimate whether or not it's worth it to be so totally open and vulnerable to him. Just some thoughts.
Cool. So why don't you just be a good friend to him for now while he recovers from his breakup? If he's no longer dating, chances are he'll have more time to spend with friends like you, so maybe see if he wants to hang out with you more.
You need more evidence he is into guys (you, in particular) before you start thinking about a romantic relationship. Have you come out to him?
Yes, what Resu said. I just was suggesting you go one step at a time, but he's right to warn you not to get too emotionally/romantically involved until you understand if he's even gay or bi.
