HS Crush?

Ok so last night I came out to him lol. We we were having a realllllllly really super flirty conversation and he was being so cute haha and then we started playing the question game and we were asking questions that led to him asking who my last relationship was with. Having dated a guy I used to work with a few months ago, I simply told him "Someone I used to work with" but he kept persisting asking me what "their" name was, and if he would know "them", and why i was being so "secretive". (Notice the non-gender related pronouns he used. He knew exactly what he was getting at I assume.) He then told me that I could trust him and could tell him anything. So I told him that "his name was X) He seemed generally unsurprised about the revelation, just as I thought, and then told me to ask him anything I wanted. So I pretty much tried to get at the subject of if he was gay or not. He gave me answers that were very vague. Then, at the end, he asked that if i ever dated anyone from our high school if i would keep it a secret. I said "yes that I definitely would" he asked if I liked anyone and I said yes. I asked if he liked anyone and he said "I'm not sure idk" I asked why aren't you sure and he said "I'm confusing" Then he went to bed. Then, me being kind of pissed off that I opened myself up to be left with a lackluster return, I messaged him that "I, if anything else, am someone that he can trust with anything. I hope by the way I just confided a huge part of my life to you, that you can see that anything you tell me will not go anywhere, just as I know the same with you" and then i said something about how junior year was a transformative year for me and i hope it would be for him as well. Then i said goodnight and I would see him tomorrow. What do you guys think? Some crazy revelations in there but the gist is this:
He knows I'm gay
He continues to flirt with me and has asked me questions about relationship stuff
Although he does say that he dated girls in the past, he has deliberately been vague about his orientation

It seems he is not quite ready to come out to me. Perhaps he hasn't come out to anyone before. Do you guys think he still is gay, or do you think if he was, that he would have told me. Should I continue to text him and wait for him to bring it up again or should i try to go into that deeper level of conversation again and see what develops? Idk why does everything have to be so difficult haha

 

Thanks guys!!! I definitely agree and will follow that advice! Just wanted to clear one thing up because I read my post over and it is unclear. When I was asking him questions trying to figure out his orientation and he was being vague I was not asking things like "Are you gay?" but rather "What would you say your type is?" to which he gave a description that is applicable to either gender. I will continue to be supportive, any answer questions he might have about myself and then maybe he will work up the courage.

 

We have not talked since. Last night I texted him how his game went and he responded that it went well but he coulndn't talk because he had a lot of work. Idk what to think

 

I agree about that but then tonight I texted him and he just didn't respond, which I am kinda pissed about. I am just going to wait for him to hopefully text me first.

 

Two days now where I have waited to see if he will text me after he ignored me on Thursday. Nothing to report. This sucks...

 

Just thought I'd update even though there's not much to say. I ended up caving and texting him a few days after this and then we started talking for the next few days. I thanked him for being so understanding to what I told him last week and he said no problem! Then we started talking about the coming out process and how it was a shame that we lived in a society that forces you to hide a part of yourself. He said "I know it's f*ed up like there will always be that person who will judge you" Then we talked a bit more. After that, its been pretty light convo if we talk at all. I don't know what I can do to get him to open up to me more. Yesterday, I walked up next to him in line. He was ahead of me with his friend. He definitely knew I was there but didn't turn around or say anything. It's just frustrating and I don't know how to handle anything. A part of me wants to play hard to get again, but I don't know if that will get me anywhere.

 

Ahhh I don't have enough kahoonas to do that! Plus the lunch table I sit at now would wonder why I went to sit over there. Plus, one of the guys at my lunch table commented on how hot one of the girls the guy I like sits with is. He asked if that was her boyfriend sitting next to her (the kid I like). One of my other friends goes, no I know that kid and I'm pretty sure he's their gay best friend. Then another kid, who the kid I like plays soccer with goes, "Who X? Yeah I'm pretty sure X is bi." Another friend goes, "Wait, really?" and the kid who plays soccer with him goes. "Yeah I'm almost positive" Then the convo stops about that. I guess I could pretend that I was going to pick up the "hot" friend and my lunch table would appreciate that but after that convo they would most likely suspect that I was trying to get to know X, which would be exactly what i was doing, since I am sure most of them are at least a little suspicious about me. Anyway, it's a lot more complicated then just sitting there, especially since I don't know them. I could try to get to know one of the other people outside of lunch and then sit with them but idk about that either

---------- Post added 27th Sep 2014 at 12:57 PM ----------

One thing I was thinking about was maybe seeing if he wanted to get something to eat after the football game next week but I don't know if that is setting myself up for defeat

 

Oh I know bc I was also one of the those people and I am almost positive he is. With that being said, I don't know how to get him to admit it to me. I think only he can determine that himself

 

I am almost 100% positive that he is at least bi, but I totally get what you are saying. I have already kinda set myself up for this not working out. I have so much going on this year and there are so many other factors I just see it ending in a lot of hurt if I get too attached. I foresee it as either he somehow being straight, he not being able to admit his sexuality, he admitting his sexuality but not reciprocating feelings, or he being uncomfortable with starting a relationship while still in the closet. Any and all of the above are the most likely of the outcomes. There is still a part of me that think something is possible to develop but I don't know. For now, I am not going to text him for as long as it takes. I won't like his instagram posts, I won't favorite his tweets, I won't say hi to him in the hall. I'm thinking, if he does feel something, this will get him to text me even if it takes a week or two. It's just something new I am gonna try since everything else has failed in progressing anything forward.

 

Ok so I haven't updated this in awhile and that's because there hasn't been anything to update. I haven't talked to him in like a week and a half because I have been waiting to see if he would text me. Now that I see that that is not going to happen, I really want to text him, lay all of my feelings out on the table in one message and then see how he responds. If he rejects me, then that's fine I can move on knowing that I at least tried and know all of the information. If he doesn't reject me, well, that would be optimal. I'm just sick of this in between period waiting for something to happen. If I were to text him, should it be something like this?

Start it off by saying hi, then asking if i could talk to him or be honest with him for a minute and then say
Then say:
Listen I don't know how to best relay everything that I am feeling rn but I will give it my best shot. I just feel frustrated because I feel like this situation is so confusing and I don't know how to handle it. I really like you and I don't know if that is either reciprocated or even possible of being reciprocated, but I feel like I have been waiting for something to happen and I have finally realized that nothing is going to unless I put myself out there like this. It's just really hard in an environment that almosts forces us to not even say hi to each other at school because we, or atleast I, am trying to hide something. Honestly, I don't really know what I expect from saying this and I don't really know what I want out of it either. The only thing I know is that I really like you and like talking to you, and I hope by me sharing everything that I have with you that you will trust me. If I have completely made a fool of myself I am really sorry, and all I ask is that you honor your word when you said that I was able to trust you. If nothing else, i hope we can be friends, I just really needed to get that out in the open because it was a frustrating weight on my shoulders.

Thoughts? Will this end badly? Should I just send him a text without saying all that?