Most Helpful Girl
Yeah I have twice. Both times though I felt confident I had a chance with them. The first, I ended up telling a guy I missed him/wanted to hang out. He responded well and we fell in love and dated for over a year. The second guy was showing signs he liked me so I am currently "pursuing" him. I am normally the one to approach and he doesn't seem to have a problem with that. The second guy is awkward and insecure so I don't mind doing most of the work for now haha.
If you think there's a chance I say go for it. If you aren't sure approach him in a more friendly/less flirty way.