new bf says he makes ex's sign an NDA

[anonymousgf]

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?

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[Pook075]

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.

[ForeverDad]

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?

[Alex V]

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.

[Skip]

Is signing an NDA really normal for wealthy people?

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.

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.

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.

[Under The Bridge]

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.

That one massive 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.

[Rowdy]

That one massive 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.

[CC43]

Hi there,

I'd say, go with your gut on this one.  I find the threats and intimidation to be very off-putting.  I've signed dozens if not over a hundred NDAs in business and employment dealings, but I was never, ever forced to sign anything.  You could say as much:  I'm not comfortable being forced to sign anything.  Another way to say this could be:  I'll have my lawyer look at it if and when the time comes.  If he asks you to name a lawyer, just say you have a trusted cousin, uncle or colleague, something vague.  He shouldn't balk at that response because it's customary to have lawyers review any important documents before signature.

But it sounds a little to me like this guy is bragging.  He thinks he's so important he needs you to sign an NDA?  He's willing to pay you 20 grand to get you to sign it?  He's paid past ex-girlfriends to do this?  It sounds to me like he's overcompensating for his insecurities, as well as treating girlfriends like commodities to be purchased, coerced and/or discarded.

[Notwendy]

I didn't read the book or see the movie but heard it talked about. The character Christian Grey (as in 50 shades) had his partners sign an NDA.

But this guy is also paying people to sign and threatened you if you didn't sign it.

Makes me wonder what did this guy do to his exes that he has to pay them to  sign an NDA to not talk about.  And if so- do you want him to do this to you?

The other possibility is that it's BS and he's delusional. But if so, do you want that too?

The only situation where I could think of this being a legitimate concern for him is if he's a well known celebrity and doesn't want his private life sold to the tabloids by an ex. But celebrities may also be creepers in private.

I think the best take is that people who have nothing to hide in romantic relationships would have no need for an NDA.

[Skip]

Setting the threatening aspect aside for a moment…

Breakups can be messy for many reasons. In my 20 years of reading here, I’ve seen some extremely vindictive post-relationship behavior—from both our members and their former partners. The concept of an NDA, by itself, is not a character flaw. In some situations, it can be a prudent precaution.

What I find interesting—and potentially credible—is that he does not seek an NDA upfront, but rather at the end of the relationship, when a partner would theoretically have the most leverage if he had behaved badly. He is also offering $20,000—an amount that would be difficult to refuse if there were no foul play on his part, yet insufficient if there were serious misconduct.

That suggests the NDA may be intended primarily to protect against vindictive behavior after a breakup—such as contacting his employer, his children, or posting identifying or damaging information online—rather than to conceal serious wrongdoing.

One reasonable step would be to ask to review a copy of a prior NDA, with names and dates redacted, to better understand its scope and intent.

[Skip]

Just a small comment on "follow your gut". We often encourage members to rather "be mindful" for complex things like this.

Key Differences at a Glance

Aspect----------------- Follow Gut    Be Mindful

Speed------------------- Fast, instinctive    Slower, deliberate

Basis    Intuition, emotion, pattern recognition    Awareness, observation, reflection

Best for    Time-pressured or familiar situations    Complex, emotional, or high-stakes decisions

Main risk    Bias, projection    Overthinking, indecision

[Under The Bridge]

Sometimes we can think far too much, to our detriment.

I bet a hell of a lot of us here who were mindful later wished they'd just followed their gut at the time and saved much future pain. I know I wish I had, then I'd only have had 6 weeks grief instead of the 4 years I got.

[anonymousgf]

Update: I texted him last night and told him that I was concerned about the threatening statement he made and basically called out what he did as being coercive, intimidating, and makes me feel less safe. He responded saying "You can always leave" and then showed up at my apartment at midnight intoxicated and said "I feel alive, I want to cuddle". I tried to discuss my text and he minimized it in the moment and shut down the conversation. He fell asleep shortly after. In the morning he tried to act normal and I reiterated that I was upset. He finally was able to discuss it and he apologized. He said I wouldn't have to sign the NDA and he will just have to trust that I won't do anything that would hurt him. He said that he has done NDAs in the past because of his personal control issues (stemming from BPD). He said that his threat regarding making my life harder was him "just making _____ up" and said he wouldn't actually do that. I don't know what to make of this. It still rubs me the wrong way that he would even joke about that

[Pook075]

Update: I texted him last night and told him that I was concerned about the threatening statement he made and basically called out what he did as being coercive, intimidating, and makes me feel less safe. He responded saying "You can always leave" and then showed up at my apartment at midnight intoxicated and said "I feel alive, I want to cuddle". I tried to discuss my text and he minimized it in the moment and shut down the conversation. He fell asleep shortly after. In the morning he tried to act normal and I reiterated that I was upset. He finally was able to discuss it and he apologized. He said I wouldn't have to sign the NDA and he will just have to trust that I won't do anything that would hurt him. He said that he has done NDAs in the past because of his personal control issues (stemming from BPD). He said that his threat regarding making my life harder was him "just making PLEASE READ up" and said he wouldn't actually do that. I don't know what to make of this. It still rubs me the wrong way that he would even joke about that

As others have said, you must follow your gut and make a clear decision.  Don't just "go with it" to see what happens.

[Notwendy]

Although you have known him for a year- he asked you to be his gf a few days ago.

This is a very new and early relationship and you have concerns. The longer a relationship continues- the more difficult and complicated it is to end it if that is the decision.

You are at a fork in the road with this. One option is to go along with it and "see what happens". This is the passive decision. You just keep on as it is.

The  other is to consider the issues that are concerning to you and decide this isn't the direction you wish to take with this person and take action and break it off.

You have looked at this person to decide on the relationship- the NDA, the showing up drunk, to making light of his threat, showing up unexpectedly, and intoxicated expecting to stay the night.

Now, also look at you, look inward. How do you feel? You feel confused, you feel your concerns are being dismissed, invalidated. You feel intimidated and unsafe.

What do you want in a romantic relationship? Think about this and does this match what you are experiencing with this person?

[Skip]

"You can always leave"

I don't know what to make of this....

At 35,000 felt, you are chasing, and he is feeling pretty entitled and testing (consciously or subconsciously) your boundaries.

In a relationship with a person with BPD traits, you have to be strong. Part of that is zero tolerance for doormat treatment.

When someone says "you can always leave", hit the pause button and wait for him to comeback knocking. Be strong. Stand up for yourself. Keep the "power dynamic" in check.

[Notwendy]

Money is power too. Seeing the concept of "power dynamic" reminded me about how my BPD mother controlled people with money. How she spent money was emotionally driven.  Accepting any money from her had strings attached.

She prefered relationships with people who had less income than her- and this kept the power dynamic in her favor. Speaking to some of them, they assumed she was wealthy.

However, there was a disconnect between her emotional spending and the logic of numbers and the actual money she had, and her emotional spending eventually led to her being in financial difficulty. 

Observe how he relates to money and others. Taking you out for a nice dinner- that's a nice date- but using money to control and influence is different.

[anonymousgf]

I just found out that my boyfriend has been lying about his identity from the beginning of our relationship. I have questioned his job and he faked a deposit to prove he was employed at this somewhat elite company. He left his ChatGPT open on my laptop and I saw him asking it about how to fake a deposit for the human eye and asking specifically for that company. These messages were back in April, 2025 in the same feed discussing his ex who was also suspicious of the same thing. We were dating in April, and I guess he cheated on her and was trying to get her back at the same time we were dating. He has created a persona of being a wealthy man, and his ChatGPT history shows a somewhat weird fascination with "elitism" and how to fit into that category. I contacted his ex and she said, "I truly have no idea who he is, how he makes money, etc. and I think he probably lied about most things he told me about him during our relationship." I feel like I am going crazy. I don't have friends in my area and I am so scared to be alone but I know I can't stay with this man that I don't even know. I don't think that I will ever trust anyone again.

[Pook075]

I just found out that my boyfriend has been lying about his identity from the beginning of our relationship. I have questioned his job and he faked a deposit to prove he was employed at this somewhat elite company. He left his ChatGPT open on my laptop and I saw him asking it about how to fake a deposit for the human eye and asking specifically for that company. These messages were back in April, 2025 in the same feed discussing his ex who was also suspicious of the same thing. We were dating in April, and I guess he cheated on her and was trying to get her back at the same time we were dating. He has created a persona of being a wealthy man, and his ChatGPT history shows a somewhat weird fascination with "elitism" and how to fit into that category. I contacted his ex and she said, "I truly have no idea who he is, how he makes money, etc. and I think he probably lied about most things he told me about him during our relationship." I feel like I am going crazy. I don't have friends in my area and I am so scared to be alone but I know I can't stay with this man that I don't even know. I don't think that I will ever trust anyone again.

The red flags have been confirmed.  Now's the time to buy a tank of gas and start driving towards friends and family.  If you don't have a car, then check out the local bus routes to get back home.

This thread is in the category "bettering a relationship" so the advice should be towards repairing the relationship.  I don't see how we can do that here though since you don't even know who he is.  I do not think you should confront him in person, just a gut feeling from this whole thing.  Get away first and then you can have that conversation.

[PearlsBefore]

I'm confused and curious if he's just a poseur trying to "impress/intimidate" you...seems to me anyone in the situation to have an NDA to reveal themselves to you (maybe he's an NFL star, maybe he's a millionaire, maybe he's head of some prominent activism group)...would want you to sign it BEFORE entering a relationship...not at the end.

That's the real red flag to me - who is smart enough to know about NDAs, but dumb enough to leave it up to dumb luck and a pittance (20k) to cover their ass?

[ForeverDad]

That's the real red flag to me - who is smart enough to know about NDAs, but dumb enough to leave it up to dumb luck and a pittance (20k) to cover their ass?

This sounds like pure narcissism where this confidence man (con man) expects people not to eventually catch on to his convoluted stories and dump him promptly.  They expect their targets to be so credulous (believing everything) as to ignore the obvious signs of emotional manipulation and misuse of the trust expected during a close relationship.

[PeteWitsend]

I have a couple thoughts below:

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.

Being "extremely secretive" is certainly a 

I take this to mean you are not currently his GF, and have just been friends?  Is he pushing you to agree to sign an NDA before you become BF/GF, or is he saying you'll sign an NDA now just because of your friendship? 

One thing you shouldn't agree to is to agree to sign an NDA before seeing it... and ideally paying an attorney to review it (which is maybe an hour or two of legal work. not a big fee).

Is this just fear of abandonment turning into containment or is he trying to hide his past behavior?

If I had to wager why he's presented this, it's because he's essentially a "sugar daddy" here, looking to have some fun with someone (i.e. you) until he gets bored, then pays you to go away. 

Now I could be wrong... but it sounds like this is an established pattern for him, and he expects the relationship with you to go the same way. 

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?

I'm assuming he wants to have his kicks when he's with you (whatever they are; drinking, drugs, sexual, etc.) and even if they aren't that far out of the norm, he values his privacy - as we all do - and doesn't want a jilted ex- trying to blackmail him to get more money with pictures or stories of their time together.  If he's wealthy and has a public reputation, he's going to be cognizant of that, and pictures - even relatively tame ones  - of him cutting loose would conflict with that. Now, exes could blackmail him even without an NDA of course, but having the NDA gives him another stick to hit them with to behave.

That's not a good sign he's already trying to coerce you into signing it. 

As far as whether they're common, I think as we get more and more extremely wealthy people, and the disparity in wealth and power between them and everyone else grows, they're becoming more common, and the world we live in is changing... 

[PeteWitsend]

I'm confused and curious if he's just a poseur trying to "impress/intimidate" you...seems to me anyone in the situation to have an NDA to reveal themselves to you (maybe he's an NFL star, maybe he's a millionaire, maybe he's head of some prominent activism group)...would want you to sign it BEFORE entering a relationship...not at the end.

That's the real red flag to me - who is smart enough to know about NDAs, but dumb enough to leave it up to dumb luck and a pittance (20k) to cover their ass?

yeah that, too.  I mean, you don't do things you want to be held confidential by the NDA BEFORE you get a signed NDA.

In business, we don't disclose confidential things to a potential partner, then say "Okay, now sign our NDA"

Makes me think, like I said, the NDA is more his way of paying an ex to go away amicably when he's bored of them and wants to move on.

[PeteWitsend]

EDIT: I missed the post about him showing up drunk and wanting to cuddle.

He sounds less put together than I assumed when I wrote my longer response!

Guessing he's one of those guys who's reading posts from the "Manosphere" and influenced by something some idiot said.

Call his bluff... ask to see a copy of the NDA, and say that if you agree to sign it, he's got to put $20K in an escrow fund with a stipulation to the agent that as soon as you sign that agreement, the money is remitted to you.  And he has to pay the escrow agent's fees (no big deal.  he's right right?)

[PeteWitsend]

Also, signing an NDA is meaningless if the person you're suing isn't rich, or doesn't have assets you can collect against (e.g. they don't own a house).

So his ex signs and NDA, and then divulges the context of their relationship publicly... somehow.  I don't know, posts pictures on facebook, or tells his secrets or private communications.  Now he has to decide to sue them for breaching the NDA.  That's going to cost him a lot of money... at least ~$25K just to file. 

Say they defend themselves and fight back.  Now you're looking at a full trial possibly, and getting into six figures in legal fees for each side.

Now say he wins... what are his damages exactly?  The other party may have to pay his legal fees.  Can he demonstrate that he suffered some sort of harm to make it worth it? 

Let's say for argument's sake he can show that his business suffered, and he lost out on a million dollar contract because his ex breached his/her NDA.  Does the person he's dating have anywhere near that amount?  Probably not    So his BALLER move of having his exes sign NDAs is just bluffing

[CC43]

I'll repeat my prior observation:  It sounds a little to me like this guy is bragging.  He thinks he's so important he needs you to sign an NDA?  He's willing to pay you 20 grand to get you to sign it?  He's paid past ex-girlfriends to do this?  It sounds to me like he's overcompensating for his insecurities, as well as treating girlfriends like commodities to be purchased, coerced and/or discarded.

How about this?  Don't sign any NDA.  Don't even bother looking at it.  Don't accept money from him, if he has it anyway, which I doubted from the beginning.

Just my two cents.

[ForeverDad]

If he has a pattern of insisting on NDAs, what does this say about his track record in seeking relationships?  What does this say of his respect for his partners when he expects them to become ex-partners?  What does this say about what he thinks of you?

As a side thought, with him cycling through multiple relationships, it might be wise to insist on proof of no STDs, though even that is no guarantee.