I've known this guy Jon for about 4 years. A few years ago he was engaged but his fiancé left him for someone else. I had the idea of giving him a little space before asking him if maybe he and I could take a shot at seeing where things could go. But he met someone else before I could say anything. Both of us single (he recently) now have spoken a little bit lately and this idea has come back. I know what I risk by telling him, yet I know if I try to wait for that "perfect moment" I could end up right in the same spot again. He meet someone new and I haven't got to say anything.