Friend Needs Help and I'm Not Positive What to do...

***I'm warning you this is a long post***

Ok, I've got a friend, let's call him Joey. I've known Joey for about eh 9-10 months now. I know him because he dated a friend of mine Emmy (who's a girl) for about 2 months. After they broke up I was curious what happened so I started to talk to him on my own to try and figure it out. I always thought he was straight until I started to actually talk to him and became friends with him. It took me a while to actually start to think he wasn't straight (I think he's probably bi). I just started to notice patterns in his behavior and how our discussions went.

At first when we'd talk it was pretty normal we'd talk about the girl he dated and whether or not they could get back together. Then we started to talk more and he began to open up. He's extremely depressed. He's very lonely. And he's told me a couple of times I'm the only person who he's actually opened up to. Also, in the past he's randomly asked me about gay sex or brings it up. He'll talk about how he doesn't think he could ever do it. I usually joke about it and don't take it too seriously, but when I do take a more serious approach he seems taken aback and gets very anxious. Then after every time sex comes up he brings up Emmy. Even though we never really talk about her anymore. I've never brought up sex with him, he always brings it up.

Also on more than one occasion he's told me how he loves me and appreciates me. I'm not going to lie I like when he says this. But then he will end up talking about how he wishes I was a girl. How I'd "be perfect for him if I was a girl" (his words). The whole "wishing I was a girl" thing really bugs me and it shouldn't be too hard to see why. And after all that he will then bring up Emmy again. I actually sent him one of those kiss emojis and said no homo with it joking, then he replied yes homo, then said he loved me, and that I was like a girl he doesn't have sexual feelings for.

Then there's something that happened a few weeks ago: he was drinking and we were texting and I was just teasing him like I usually do. Then he didn't reply for a couple minutes then I get a text from him saying that "I only make fun of him because he's gay" then he called me an asshole. He didn't talk to me for a little over a week after that.

I actually talked to my friend who he dated and she's told me that she knows for a fact he's not straight, she's told me a few times she honestly thinks he's gay. She's very attractive and she said she'd try to go further with him and he wouldn't want to at all. That he was very uncomfortable with anything intimate. He's not dated anyone since her. And every time he's told me he has a date since then the date mysteriously cancels (shocking right?). He tries to keep up this womanizing appearance with other people, he tries to be the stereotypical dumb jock boy but he tells me that's not who he is at all and that he puts on a show for other people. He's so ridiculously insecure.

So. Basically to sum it up, my relationship with Joey is screwy and I get that. And he's probably "not straight." I just want some advice from anyone who might have been in this kind of situation before. How to handle it. And how I could create an environment where he's comfortable being open. As much as he has opened up to me I know that there's still a lot he's uncomfortable talking about. Gay, straight, or bi, he's my friend, I do really love him and I want to help him and be there for him. I don't really care what he is at this point. I'm very lucky to have him as a friend. He's very smart and has such a kind heart it really kills me that he doesn't see that he's a beautiful and unique person. Help me help my friend.

I did post this before in another section but I just want as much feedback/advice as possible...

 

I agree with you entirely. What they don't tell you in Harry Potter is that Snapes truth serum is actually just Ketel One Vodka...