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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.

It sounds strange that he would be able to force NDA signing of an ending or ended relationship.  Where would the legal leverage be afterward?  At a guess, I'd figure that's where the $20K comes in as incentive?

I doubt a NDA would be applicable for illegal or abusive actions.  Sounds like he wants to have his fun - and avoid negative social posts, etc - even when planning to walk away?

What does your gut feeling tell you? Or is you asking here perhaps giving the answer. You may ask yourself what needs to be covered up by this NDA. It does not sound like a base of trust to start a relationship like this. And treatening you if you don't sign? Be careful.

To be binding, an NDA lists explicitly what is not to be disclosed. If he wants you to agree not to disclose the names of his business clients that's one thing, if he doesn't want you to tell anyone that he was physically abusive, that is another. If he is willing to pay someone $20,000 not to disclose business information, many people would take that.


This is intimidation/control. He may be testing/grooming your boundaries by using a carrot ($20,000) and a stick (intimidation) to see how you react.

That one massive red-flag line alone would have decided it for me. Threats are a no-no.
That didn't just sound like a business-type NDA, more like a very controlling life 'NDA'.

As others have said, go with your gut feeling and tread very carefully.

hmmm, sounds all a bit P Didley to me.
Why does he want people to sign NDA’s in personal relationships, sounds like he gets involved in risky or shady behaviours that he doesn’t want made common knowledge once the relationship ends and to be brutally honest, it sounds like it will at some point.

And where does that lead. There might be situations you are put in that leads you to feelings of guilt, anxiety, depression.
Then you may end up with an overbearing weight that you need to get off your chest, yet you can’t talk to anyone because of the threat of making your life difficult, and anyone that might approach you questioning your relationship with him will make you wonder if they are flying monkeys, and then you end up with feelings of paranoia. So your health could suffer.

You don’t just find $20k down the back of a sofa, all of those dollar bills will have strings attached.