Search Results: going to the prom

I have a friend who lives about two hours away from me, we met at a drama tournament. When we met I asked him for his number and we texted a few times that week but not that much, we saw each other the next weekend at another tournament and hung out basically the entire time. At one point we were both done with what we needed to do but we still had a few hours until the tournament was over so we decided to walk around the school. He told me that the reason he didn't text me much was because he liked me romantically and he had just got out of a bad relationship and didn't want to get attached. I was his first kiss that day and we talked for a long time. The only reason we didn't start dating was because of distance and because we had both recently got out of bad relationships and decided it was for the best. We eventually stopped talking.
A little after this year started he texted me apologizing for losing contact and told me how I deserve to be happy. I texted him yesterday and told him I'm going to be in his town in two weeks and he invited me to go to a church service for teens that he said he really likes. He seems really excited about seeing me. I asked him if he was going to prom and he said he didn't know. My prom is in his town because I do online school, so if he did want to go he would be able to.
We both really liked each other a lot back then, and I still like him. This was last school year. I'd really like to go to prom with him but I don't know if I should ask him. I want to be casual about it too in case he doesn't still like me. Should I ask him to go to prom with me?

my boyfriend is 2 years older and is super sensitive and we've talked about going to prom together (he would take me to mine since i'm still in high school) but i've been thinking lately that i wanna go with my guy best friend? is it bad to wanna go with him instead of my boyfriend? if you were my boyfriend, would you be upset? he's really sensitive and i think he'd be upset but i'm not sure if it's reasonable for him to be upset

Or homecoming? How would you do it (would you go all out with a sign and balloons or flowers, or just ask verbally?) please note I don’t mean on a date. Just to prom or hoco specifically. And under what circumstances would you give up on him asking you out and just ask him out instead?

Please don’t give me tips or whatever. I just need those three questions answered.

1. Would you ask him out in the first place? [poll]
2. How would you go about it?
3. Under what circumstances would you ask him (not like, “in the evening”. I mean more like “if I’ve hinted to him I’m going and he hasn’t asked me,” or “I wanna go with him but he isn’t asking me,” etc?)