When do you know the time is right?

I just left my dear friend's house - Mr. Atlanta. He and I relaxed, watched tv but we also talked. We talked about love lives and mostly his - we all know mine is a bit non-existant right now. The big thing that came up is why is he still dating someone he doesn't sleep with much (I know), but more importantly doesn't spend much time with and get along too well with. And this is the second or third time he has been with her. Same girl who broke vases, etc. his condo back in December. In all respect to her I never met her and I can't speak very negatively of her but I don't get how either of them can be in a relationship that has fizzled out sooo long ago. I stayed in my last relationship for nine months but we saw each other mutlitple times a week... it wasn't perfect - we didn't go out in public too much unless it was to our bars or friends but he did work until 10 pm every night but Sunday and Monday. It wasn't perfect but we tried and truly did talk alot and see each other a lot.

I don't want to judge Mr. A's relationship and he knows my concern of saying "why?" is not so I can date him but so I can see him happy again. I saw that brief glimpse over Christmas and I miss that from him. When do you know the time is right to say "this is the right time to let go." How do you know?

us from a few years ago...