Asking out a, shy guy friend Options

[bambamboozle]

So I have a friend who's really shy, and I like him.
I just went with him to a dance and had lots of fun (but I played off asking him by saying just as friends)
And my friends (who are also friends with him) think that he likes me too, so I'm gonna tell him.

The only problem is, we're both always so quiet and awkward with eachother and if he doesn't like me, I don't want it to ruin our friendship...plus it seems hard to get in a situation where I could actually tell him.
Oh, and he's a senior so I'm only guaranteed to see him this week and then one week in the summer when we have this event. Otherwise I'd have to flat out ask to meet up with him.
Any help with how I can tell him or play it off if it's obviously weird?

[ame;]

These situations are always weird. but i say go for it, if you ask him out of course you guys will meet up to be with each other troughout the year
You dont have to ask him straight out, maybe ease yourself there, like ask him out on a date? Even though you guys are friends already .
Seriously dont wait, or leave it, you'll most likely regret it later .

[loveylovely]

I have this very same situation, except this guy's not shy or anything.. but I just so go with the flow. Get him to have a conversation with you and ask him what he likes to do. Then just casually say something like, "Well maybe we could hang out sometime during the summer doing that.." Just whatever comes naturally. He'll probably say yes.

Since he's really shy, you'll have to lead the convo most likely.

[ame;]

I have this very same situation, except this guy's not shy or anything.. but I just so go with the flow. Get him to have a conversation with you and ask him what he likes to do. Then just casually say something like, "Well maybe we could hang out sometime during the summer doing that.." Just whatever comes naturally. He'll probably say yes.

Since he's really shy, you'll have to lead the convo most likely.

yeahh , i agree, ask him if he wants to meet up during summer, tell him your going to miss him, and just keep up the conversation, if you dont want say it right out just try and get closer to him with things like going out places, and spending as much time with him .

[Mystic Eyes]

I agree with what the others have said. Ask what he's into, try to do those things with him during the summer and most importantly don't rush anything but don't leave it toooo long. Also have fun with him. Humor and enjoyment are great ways of bonding together.

[JonathanK]

Ask what he likes and talk to him about it ex. If he likes hockey talk hockey to him no matter if you hate it or not, trust me it makes us feel good when people listen.
And just ask him out no matter what anyways. Life is about taking risks if you don't take risks your not going to get very far or have a happy life. If he says no of course it might be awkward for a while but atleast you know you tried other than sitting at home one night asking yourself weather you should of and weather it could of worked out and turn in to something. So all in all ask him out.

[EmoEyelinerx]

I have this very same situation, except this guy's not shy or anything.. but I just so go with the flow. Get him to have a conversation with you and ask him what he likes to do. Then just casually say something like, "Well maybe we could hang out sometime during the summer doing that.." Just whatever comes naturally. He'll probably say yes.

Since he's really shy, you'll have to lead the convo most likely.

agreed