So, I know this cute guy and I want to ask him on a date. The only thing stopping me, other than the usual nerves, is that he broke up with a guy a month ago. I spoke to a person who knows him and she said go for it, but I'm still hesitant. I don't want the possibly resulting relationship to be a rebound from the last guy and I really don't want to upset him by asking him when he's not ready.
Well, if you're worried about his reaction, maybe invite him to go to the cinema with a group of friends first. If he accepts and feel comfortable, ask him to take a coffee, with you a few days later, and if he seems to be fine and that you have a nice time together, then ask him on a date. One step after the other
Hmm ... I'll to see if some friends want to do that. Thanks! What should I do if I can't find a group of friends who can go see a movie with us?
Maybe just try to invite him in a casual way to do casual things : going to a movie, coming over to watch DVD or playing video games, taking a cofee somewhere or going to do some shopping... Whatever you'd like to do with him. If you have a nice time and that you feel he is enjoying it, then take the next step and ask him on a date.