I guess, but what if there wasn't a 'good time' to bring it up? Could've been with her for much longer than necessary and have been hurt more also would've ruined the relationship between the best friends (the how long did you know and didn't say anything conversation) the best friend could've dropped subtle hints. But then the friend might have just seen him as a hater? I don't know - sounds like a damned if you do damned if you don't situation