I don't even know what to make of this... obviously its a red flag I know. After almost a year of knowing each other, he asked me to be his girlfriend 2 days ago. Last night we went out and had a few drinks. While we were eating, he told me that with every ex boyfriend or girlfriend that he has had, at the end of the relationship he paid them $20,000 to sign an NDA. He is well off and extremely secretive/ hard to get to know so its definitely possible. Is this just fear of abandonment turning into containment or is he trying to hide his past behavior? I told him I wouldn't sign it and he told me that I would sign it because he has a lot of connections and would make my life harder if I didn't sign it. He told me that he does it because he is worried about his reputation. Is signing an NDA really normal for wealthy people?
Hello and welcome to the family! NDA's are more common for wealthy individuals, especially in business, so it's not completely unheard of. It is a bit strange bringing it up at the start of a relationship that you'll sign one at the end.
I've had many clients in the past though that wouldn't have a single conversation until we both signed NDAs. One turned out to be a billionaire who was in a lawsuit with one of the most powerful families on Earth...I never would have guessed that beforehand. The NDA allowed us to speak freely though about his company, their strategy, and some trade secrets he was filing patents on; there was no way I could have worked with him otherwise. He did this because previous employees who didn't sign NDAs were bribed by the powerful family to share those trade secrets.
Anyway, this is normal for business and it's semi-normal for relationships by people focused on business and wealth. It is also a major red flag though where his priorities lie, so I'd be very careful.