Friend is engaged for the 5th time all the 4 previous wives were big toxic nightmares who took him to the cleaners.

advice

Friend is engaged for the 5th time all the 4 previous wives were big toxic nightmares who took him to the cleaners.

First wife was probably the worst she took most of his inheritance as he's a trust fund baby. He asked me for advice and I said shes got a ton of red flags so maybe you shouldn't marry her. He called me several times asking what to do, he didn't listen so he married her and she cheated on him the entire time and divorced and took most of his money.

2nd wife he kept a secret from me. She was big druggie, and actually over dosed before I even knew they were together or got married.

3rd wife another psycho who burned down their house in anger and he had to get a restraining order. Same as wife 2 he never even told me about her.

4th wife a combo of wife 2 and 3, again he didn't even tell me about her and went MIA as she wouldn't let him have a cell phone or respond to phone calls/texts or even emails.

5th Wife TO BE seems like pretty much all that was wrong with the first 4 wives. She did allow him to hang out with us ONE TIME since they got together and got all pissed because he came home 45min late which was only like 10:30PM. It's not like he came home at like 3am or something. She's already making him sell his house and business to move 6 states over to live with her in her small condo. Her work makes her travel to California, NYC a lot but she doesn't even live in either state.

She seems like shes out to clean him out like the previous 4 wives and also what I don't get is why he has to always get married. It's like he doesn't know you can date someone or just be in a relationship with someone without actually marrying them and giving away most of your wealth each time they divorce you shortly after?

What would you do if you were in my shoes when he asks about the 5th wife to be?

Posted Jun 30, 2026, 2:43 AM UTC

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