should I or should I not?

I think the kid that I like likes me. So I don't know if I should or shouldn't ask him out. I mean like I think he likes me because of the way that he acts around me and that he keeps dropping hints that he might like me or that he might not. Like the one moment that sticks out to me is last weekend he was spending the night with Nat and while he was over he ended up letting me draw on him and when I stopped for a minute because i thought he wanted me to, and then he randomly asked if I was still drawing on him and I told him know. He let out a deep sign and asked me if I could please keep drawing on him. Like bruh!! That shit was so fine and the amount of time I keep thinking about is mind blowing. But I also might be tripping but I did hear him say that he might like guys and might like a trans person. I am the only trans person he knows. Shit got me bugging but in the same way I don't know if he does like me. I really do get weird with this shit and it doesn't go well. but like this is really important to me. Massively. i am so in love with him and I think he might like me because the day or two after he told me that he told our group chat that he likes men. I mean I feel like I'm looking into this entire thing way to much and sadly I might just be. I mean I know that he doesn't like my best friend because I asked. but like in the same way that shit says a lot. its just the way that he acts around her and talks to her that gets me that way and makes me jealous. I've really never loved someone so much and that shit had me losing everything. I really do have issues with my crushes. The way that my crushes go is I love someone so much and they hate me or I just ask them out when I don't have a crush on them because I find one thing about them that I like. I found so many people and did that to them. I never talk about weddings and futures with my actual people I want to date because that shit is the trigger to the end of everything. But like for E he doesn't really know what he wants to do in the future. I just know that he doesn't want to have kids at all and that if he wanted kids he would probably end up ending himself. I am the same way, I don't want kids for any reason I fucking hate them and my little brother brings me to my breaking point every day. Like this entire thing is all over the place and I'm sorry I am very tired and am extremely bored. But yeah, I don't know if I should ask him who he likes or talk to him about this or something. I don't know man.