Make sure his self-esteem isn't in absolute dumps. If anyone ever were to actually ask me out (which they never will because I'm an ugly loser who nobody likes), I'd suspect either a mental disorder or a cruel trick. Doesn't help that I've had that cruel trick aimed at me before. Twice. Dodged both times; first time because of a friend's warning, second because one of her goons was being just a little too blatantly sarcastic when she complemented me (followed shortly by a much nicer person showing up and telling them to stop).
Personally, I can't tell flirting from insulting/sarcastic harassment. Of course, I'm denser than your typical nerd... I think.
So be forward, but don't flirt. Actually, I just straight up can't read peoples' intentions, so I tend to assume the worst either way. Which I really need to fix.
Homecoming is coming up here too. Friends around me, I have all of... two. One is female and doesn't want to go but her mom is prettymuch forcing her to, and although I would love to ask her, I can't, because she barely puts up with me as it is, and two of her friends...
strongly disapprove of my continued existence. I used to have two more friends, but then I sent one some stupid stuff when my meds weren't working and I lost em forever.
Given that I only have two friends, I'm too afraid to risk it.
girls don't ask guys to homecoming
What century are you from, pal?