Hey There, Katie and May here, the best matchmakers in LA, to give you some advice. Guys have it tough. They ask the women out, they plan the dates, they take the rejections, etc. It’s nice to ask a guy out, especially if you’re inviting him out on a second date. If you don’t feel comfortable doing the first date asking, that’s fine, but once you know he likes you, it’s okay to ask him out for the second or third or eighth date.