If you believe he'll listen to reason, do it.

If you don't believe he'll listen to reason then it doesn't matter what you do or say, in which case you might as well remain silent.

Yep. I told my best friend he was making a mistake. We haven't spoken since. Less than two years after the wedding the cops were at their house, step son assaulted my friend. Divorce.

Did I mention we haven't spoken since?

I felt I had to say something at the time, he being my best friend. Though I was ultimately correct in my advice, I did lose a friend. I should have kept my mouth shut. We would still be friends.

Tell him. It is what friends do. Three days and she is going nuke, tell him. And yes he sure as hell needs a pre-nup. Her response is EXACTLY why he needs one. Ask me how I know!!! It was my biggest screw up ever.

You did the right thing. It may be hard for your friend to find his way back to your friendship.

Friends look out for you no matter what the consequences, that, IMHO is what you did.

"She went nutso on him last night when he asked her to sign a pre nup." Well, have him stick to his guns. If she won't sign it, that's a fairly clear sign of her intent and he doesn't need to marry her. Give her some time to come around.

"Poor guy slept in his car last night." I've never done this in my life. Can't see why anybody would need to do this, as opposed to kicking the other half out. It's his house, not hers.

"She just moved in with him 3 days ago." No need to get married anytime soon. He should see how it goes for a couple years.

"He gave her the entire upstairs, and he moved into the basement." This is just ridiculous.

"I dont think they even sleep together." This doesn't describe someone I'd spend much time with, let alone marry.

"She is mean" This won't get better.

"She drinks" This won't get better, either. Just wait until she's really unhappy.

Frankly, this guy has no clue. If he's a good friend, I'd have a real serious chat with him.

JR

One of my buddies was getting married. About a month before he told me he and his to be wife were in counseling. I told him to put off the ceremony and slow things down until they figured things out. He married anyway. He was divorced about 2.5 years later.

He re-married and is quite happy. Weird thing: his first wife married his best friend from back home (she didn't live anywhere near there...). He also keeps connected via Facebook.

Maybe he feels like a heel for not listening to you. Have you tried talking to him?

This.

Similar situation to a friend of mine 20+ years ago. We all told him don't do it. He did anyway, he was lonely. It ended EXTREMELY badly for him. He thanked us after the divorce for trying and was sorry he didn't listen.

did she sign it or not?

He may be a grown man, but he isn't an adult. Frankly he needs a good therapist to figure out why he's making really bad decisions. "I don't want to be alone" usually means, "I am not happy with myself" and no woman or friend is going to fix that.

Always marry a woman who has more money than you.

Sorry to say this, but your friend isn't playing with a full deck. It's hard to imagine common sense registering with him, but I agree with trying. Hopefully she's bad enough to wreck things on her own before they get married.

As per usual, tons of good PPOT wisdom here...not much that I can add.
Back when I was young and dumb, I had the experience of having friends "see" things that I didn't and he/they never said a word...and I was pissed with them.
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Let me think...I'd say to talk to him...wait until they have a major disagreement.
He may be more open to what you share about what you think...and not what you feel.
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And then this:
"Show him this thread! Prenumpt is a no brainer. No prenumpt no marriage. Period."
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IMO, when/if a woman balks at a pre-nup she's showing signs of a Gold Digger...and/or a Dependent Personality Disorder.
If she agrees to it, then we can waive the pre-nup...our choice.
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And this:
"Her response is EXACTLY why he needs one. Ask me how I know!!! It was my biggest screw up ever."
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Suggest that they go to Pre-Marriage Counseling...you might even search around for a respected local therapist...make it easy for him.
And finally, suggest that they postpone getting married.
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I like this...but you may not be able to say this to him:
.
'

Yes!
At least one who is content with her chosen life goals.
If she's financially content, more than likely she's not wanting to be with us due to ulterior motives.

If my wife was looking for money with me she really screwed up.

My knee jerk response would be say nothing.
however after reading the rest of your post she sound nucking futs!
And as nostatic says he doesn't sound like he is firing on all cylinders.
I am guilty of thinking with the little head but this situation is WAY over the top.

To consider, I don't know what the divorce laws are like in your area but here the ex is only entitled to half of what you acquired after you got married. However of course depending on lawyers YMMV.

Best of luck to you and your friend.

Lost a childhood friend by trying to tell him the girl he's head over heels for is not for him. Poor SOB has a wee one and is stuck for the long haul.

You can tell him, bit I don't think it will help and may just drive a wedge between you two. The only chance you would have would be to be sneaky and talk to him in such a way that he thinks it's his idea. I don't know how to do that, but I've seen someone do it.

It sounds like he hooked up with my SIL. Good luck to you all

Honestly, he is a SUPER SUPER nice guy ,but he is not firing on all cylinders. He has some issues. Im guessing there are some meds in his medicine cabinet .He is the kind of guy who would do anything for you, but he also lets people step all over him. Every time he gets a lady, he turns into the biggest idiot I have ever seen. He opens the vault up and gives them the key to the city.
He likes to act like he has more money than he really does, and it always seems to attract the same type of woman, Ive seen it over and over.
I can smell this one from 3 miles away. There is no way she loves him, she treats him like ****, and is just waiting to sink her talons in him. There is no way in hell he can possibly be happy .
I really wanna sit down and have a talk with him, just not sure of my place here

Not so much a heel as embarrassed, is my guess.

I've scrounged around various sources a few times looking him up over the years. Not a clue as to where he might be.

I occasionally entertain the idea of what a surprise it would be for him to contact me out of the blue.

Could happen.