I was talking with her about it and brought up them again just in conversation of how she knows his personality to be vs. what I've experienced since they were fwbs. She ended up showing me their messages which ended a while ago but were one-sided as in she wouldn't respond to him and he'd hit her up a few weeks or months later trying to hookup and overall there were 5 from him spanning over a long period. I know many guys do this to a point (trust me its annoying and we hate it) and I am not jealous or anything like that BUT I am a bit turned off by how desperate he seemed. he's a very attractive guy and has slept with many girls, so this sort of ruined that cool guy demeanor in an unattractive way. I mean how many messages unanswered until a guy gets the hint, especially with an friends with benefits.
I will never bring this up to him and I know its immature but I see him differently somehow. I am not like 100% turned off by him but its embarrassing on his part.