My friend (38) has had an on-off relationship with his now ex (57!!) for the last year. I think they broke up 4 times now.

She: Looks every bit of 57. Has 2 young adult children. Minumum wage job. Has been married twice before (cheated both times because feelz) and somehow has a hold over my friend.

He: 20 years younger than her, not bad looking, low confidence, earns 3 or 4 times more than her. No kids. Never married. Has a house/car and money in the bank.

Every few months they break up, he says they aren't getting back together and hangs out a while. Then he starts talking to her again, they "compromise" which means he changes his behaviour to suit her and he it's back on. He never seems happy when he is with her. I don't understand it.

It's currently off again. He was OK 2 weeks ago, but I saw him last night and he seemed miserable... almost depressed. I knew it was about his ex, but didn't bring it up.

He's someone who could really benefit from the MGTOW lifestyle, but he needs to get over this chick.

What can I say to him that's going to make him see that she is a bad deal for him?