So, I recently stumbled upon, by the way of Facebook, that one of my friends is a Lesbian and, has most probably, been a lesbian for a long time. this comes after years of her hiding her relationships and, admittedly, slight suspicion about her sex life.

Anyway... one of my friends was in love with her. Might even still be. She knocked him back a few times after he confessed this to her and... He still brings it up as 'the one that got away' or something...

Do I break his bubble by explaining that he had no chance with her? Or does it even matter? Will it be best to tell him rather than letting him find out on his own?

More varied: Where do you draw line in being a friend to be honest to them and being nice to them?