I work with a sheltered very shy 20 year old with a work crush. My coworkers and I have been encouraging him to try. We agree that dating a coworker you see sometimes is a bad idea but we're trying to get him used to talking to women he's attracted to and ask for her number. Getting over the first rejection hump is a huge plus.

We've given him all kinds of good advice but he "can't" do it alone. I'm good with talking to people but not guiding such a conversation for someone else. So, how should I be his wingman?