Some people might think that asking someone out over IM is low class. People might think you don't have confidence! But at least you would have enough confidence to ask the person out at all.
Only use this option as a last resort. Even webcam is better than asking over aim, if for whatever reason you and this person live far away. If you have no confidence and really want to ask him out, then IM should be your last resort. Even over the phone is better.
2
Make sure you have been IMing with this person for awhile. It might be really awkward if you have never IMed with him and you ask him out over IM.
3
Look at his reactions. If it seems like he doesn't like chatting with you, you may not want to ask him out. However, if he is giving clues that maybe he likes you, you may consider asking him out.
4
Give him a hint you're about to ask him out. That way if you get a negative or weird reaction, you know not to ask him out at that time. Say something like "You're really nice" to see exactly how he responds. If you get anything like "Um" or "Uh thanks." then you might not want to ask him out. If you get a bad reaction say "brb" or "g2g" and leave him alone for a while.
5
If he says something like "Thanks" or "You're nice too." then that's a good sign. Go for it. Say "wanna go out with me?" or "would you like to go out with me?"
6
Of course if you are a bit nervous or embarrassed to ask him out, say to another friend that is online "can you do me a favour?" if they say yes, say "can you ask out [name here] for me?". The only thing that can backfire with this trick is that you must make sure that the person is someone that you can trust.
7
If he/she says no, DON'T freak out, it just isn't meant to be. Tell him you have to go or say "brb" and leave him alone for a while.
8
If he/she says yes you should make sure that you are allowed to go out. Then set the when and where!
-- Edited by berzy11 on Saturday 1st of January 2011 09:31:38 PM