I've been working for some time now and I'm starting to notice a new side from my boss. I noticed my boss roll his eyes when another man mentioned about "bad" girlfriends. Keep in mind that my boss is 57. A female coworker (40) had a feeling on her first day of work that this man is cliquey and maybe gossipy. He would be nice one second but then snap with an uncalled for comment but then forget about it later. When he started to own property in real-estate, he dated and lived with a woman for some time. He doesn't have good regards towards her now that he is wealthier.
If she was such a bad gf, why did you choose her? It's possible that he used her for personal gain until he had enough/rose up in status. I'm starting to notice that more often.