How do I ask him to homecoming this year?

Hey you. Just relax, go up to him and ask. If I’m a freshman and a sophomore asks me out I’d melt. I love older women.

I think most guys would be very excited to be asked out by a girl a year older than them. I don’t think you need to make a big deal out of it. Sounds like a lucky guy to me. Good luck, I’m sure everything will work out for you.

Thing is he is rather attractive and I’m average at best.

Hey you, you are pretty hot. Just relax and be yourself.

This feels creepy to say to a young girl over the internet, but you’re very pretty. He’s the lucky one—just keep that in your head and you’ll be fine.

Thank you I think Adiromdackwannabe and I understand that gorillapaws and thank you for the advice

If you wanted to go all out, you could get some other people from your marching band together and go into wherever it is that you guys work (with permission ahead of time from your boss, to be on the safe side) on one of his shifts, play a song and have people hold a big banner behind you that asks him to go with you. Would be pretty unforgettable. :)

Also, I’d just like to say that you shouldn’t be selling yourself short – you’re very pretty. But even if you weren’t, maybe he wouldn’t care about that if you’re a pretty cool person, too.

Even if you don’t go all out to ask him, just remember to be confident about it. Down the road, you’ll regret not trying – even if he ends up saying “no”. There are other people out there who will give you a shot, regardless. Good luck. :)

As the Nike commercial says:

JUST DO IT ! !

Wannabe & Paws are both right. They’re also being too gentle with you. If the guy is cute, you don’t have a minute to waste. Unless you’re waiting for a lesson on missed opportunities, sieze the initiative, ramp up your courage and ask him NOW before some bimbo walks away with YOUR prize. You know it will happen. He’s probably hoping that you’ll ask anyway, so do it NOW & find out. Want more obnoxious advice? If he makes the mistake of turning you down, tell him “I’m older and smarter than you, and everyone knows that guys don’t know WHAT they want anyway, so you’re going with me. It’s for your own good and the best thing for both us.”

Wait a minute. Homecoming???? This is August!!!

Make sure you do it in private and don’t make a big fanfare over it. It’s not a marriage proposal! You have to give him the space to say not without guilt or shame and for you to hear a no without an audience. I think it’s a little early to be asking for Homecoming unless it’s in September but when you do do it, I would make it casual and in private.

I want to figure out an idea now so within September I can ask without having to freak-out about it

The easiest way to go to homecoming with this guy is to be dating before it starts. Why not invite him to do something with you? Go see a local college football game (some have great marching bands). Go check out a jazz performance at a local coffee shop? Visit a nearby park/river/lake? Grab a movie? It should be something you genuinely enjoy doing and not just something you think he’d like. I’d keep it low-key, fun and lighthearted. Making a big dramatic thing like you see in the movies could be awkward. Next time you see him at work, ask him out!

The times in my life I most regret aren’t the ones where I asked out a girl and got rejected; it’s the times I never asked. I’ve had a few girls come up to me many years after high school and tell me they had a big crush on me back then.

I’m with @janbb on this one. Don’t do anything public, and don’t go in with the idea of making a proposal that “he can’t turn down.” You need to be able to give the guy an easy, non-embarrassing (for either one of you) way to say no.

If this guy is interested in going with you, he’ll say so when you ask him, privately. Just ask him in simple terms like this, “Hey Justin, I’m planning on going to the homecoming dance and I was wondering if you’d like to go with me.”

He’ll either say yes, in which case you’re good to go, or he’ll say no (and probably give a real, or not real, but polite answer as to why he can’t go).

Don’t demand to know why he can’t go, even if you don’t believe him. Don’t ask him why he doesn’t like you (maybe he does, maybe he doesn’t, but it’s no reflection on you) If he gives you a reason for why he can’t go, it’s either because he actually can’t go (for whatever reason), or he’s trying to beg off without hurting your feelings.

Just don’t put him on the spot. That’s not fun for anyone.

Also, don’t stress yourself out worrying about a dramatic way to ask him. Drama tends to backfire. If you just ask him, like a regular friendly person, whether he says yes or no, you won’t have to feel awkward about it. If he says yes, then you can go and see where it takes you, if he says no, you’re still friends. If you bring drama into the picture and he says no, you’ll probably regret it, and you might embarrass him.