I have known this guy for about 15 years. We went to college together, he is about five years older than me. Back in college we were acquaintances, and hung in mutual circles. We lost touch over the years. Fast forward to about two years ago. We reconnected via Facebook and met up with another mutual friend to reconnect.
Over the past couple of years we've started growing our friendship, and I have lost about 40 pounds since we reconnected. He has been dating a girl on/off for about a year; she has broken up with him three times in the last year due to her commitment issues. During their last breakup, my friend made it clear that he had grown attracted to me, and if we were both single (I was seeing someone at the time), he would like to start dating.
Since then I have broken up with my boyfriend (not because of my friend, other issues were in play). I had never considered dating my friend until he broached the subject, and since then I have seen how we are very compatible, and I have grown physically attracted to him as well (I wasn't before). My friend has gotten back with his girlfriend, however, and asked me if I felt awkward after everything that was said. I told him no, but secretly I wish that things would work out so we could date. Recently he invited me to meet up with him and his girlfriend for dinner and the friend I was with said it was clear that my guy friend is smitten with me.
My question is, do I sit back and wait and see if she breaks up with him AGAIN and stay friends with him in the meantime, but not too "chummy" in order to keep the attraction there?