I know a guy, used to be a friend.
He had a very high opinion of himself and looked down on everyone around him. One of those "I am a political expert because I listen to an hour of talk radio every day" guys. Wanted the "Stacy's" the hot, high-maintenance, elite type women. Of course none of them would have him. Also wanted them MUCH younger. My husband and I have a 20 year age gap but he went far beyond that. He preferred 30 to even 50 years difference.
He likes sugar daddy arrangements where he controls everything, how much sex, when, how long, how much money will be given and for what, whether she can have a boyfriend, etc. He had one with a girl he put through a vocational school, she was very pretty, high-maintenance type who clearly did not want her photo taken, but he did and showed it to everyone, including me. She looked profoundly unhappy and very angry with the arrangement. I mentioned that and he said "I like it BETTER when they hate it".
He can be very attentive to women and one woman at work knew we knew him, after he retired she was asking me about him. I was vague on his love life and told him, she is really into you, do you want me to give her your number? But she had long gray hair, not long and black, she was "fat", she was "old", etc. so he said no she isn't good enough for me.
Years later he was begging for her - was she still at work, I said no, long gone. Missed the boat. And she is the type, like me, who would stay through anything and give 1000% to her man.
So this year he found another desperate woman, a middle aged waitress who is apparently fat, "old", probably gray or dyed hair. They have a sugar daddy arrangement and he was very smug about it, sharing a lot of details we did not want to hear. That was the last time we called him.
He is just so ANGRY towards women it comes out in everything, so bitter my husband found a devoted wife and he did not...lately I have just not liked being around the man... he's seething all the time.
Hopefully he has mellowed a little with his latest arrangement.