When is a good time?

Try dropping hints, if he doesn't pick up on them ask him out. If he says no, then accept it and be happy just being friends. You will have peace of mind knowing for sure.

If a guy is worth his salt, he won't take you for granted for asking him out and will be flattered. Alot of girls were friends with their boyfriends or whatever before they dated. Life is too short, go for it.

He doesn't like you stay friends, he would make a move on you himself if he was intrested in you.

Don't ever ask a man out, he will take you for granted.

Let him start things after some flirting (if he doesn't flirt back stop) he will ask you to hang out or go out if he is interested.

Tell him you like him. Say somethiing like, hey we need to talk, well you see, sometimes I just find myself thinking of you and smiling and I wonder why that is, so I think maybe we could go out to the movies or something, like on a date? Just say something like that. It should work, maybe not straight away but eventually it will.

Don't ask him out if ya'll are friends than if he isn't interested it will hurt your friendship. Send him clues but in a sexy way. Play a little, tease a little and flirt a little. Make him interested so he will ask you out. Guys love the chase.

When you felt ready. Don't rush anything in the beginning give each other plenty of space and take your time getting to know one another that way you will be totally sure you want to ask them out.

When? anytime. When you see a cute guy, when you've got to know someone for a while, anytime, just do it when they aren't around their friends or maybe pull him from the group and talk to him. You should read your horoscope.

Anytime you see him again. If everytime you see him or hear his voice and you just want to shout "I like you" then you should ask him out. The wrong way to go is to have a friend ask him about if he likes you because you never know how the message will be mixed up, just go up to him yourself or even over the phone and see if he would like to go see a movie or something just to start up the realationship.

I don't know I couldn't say as if I would ask the guy out. But if you are going to do it should be a low key night. Make sure he is expecting it you don't want to come on to strong, and scare him away.