Ok so I initially thought her guy friend was a guy she was pinning for but was always dating someone else, but since she says he's her ex, I'm thinking they dated but then she realized he's an ongoing player and then they broke up at some point (maybe when he went abroad).
As for her boss, is he saying that the former boss, the one who is getting married, was his former fiancée?
No wonder everyone is asking this stuff, it's hard to tell what's what.