Are you the type to ask a guy out, even if you’re not sure if he likes you back? Are you the type that is too shy or what have you to ever ask a guy out first?

I’m curious because I’ve been trying to fix up my co-worker who is a guy, with one of the two other co-workers he has a crush on. I get them all in the same room, get them talking, I will tease him and try to get them in on it [friendly jesting mind u], I even told them about how he wouldn’t ask anyone out unless they asked him out. I want to drop hints but I don’t want them to know he likes them or he may kill me. He has a hard time telling if a girl likes him or not.

If you weren’t sure the guy had feelings for you, and you were co-workers, would you still ask him out?

Do you have any other advice for me as I play match maker? lol