You might touch base w/this guy. ;)
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The flip side is this. Except I was the one in the first marriage. After it was all over my ex wife's female co worker said to me " I knew it would not work. You were not suited for each other". Duh. Like I needed that comment like a hole in the head!.
Guy

I'll take "Mommy Issues" for $400 Alex...

If he doesn't have self-worth, then he'll seek it from a woman, and since he is convinced he's a POS (*cough* mom *cough*), he knows the only way that he can be worthy is by giving them everything. Then he'll get passive-aggressive since he's getting stomped on despite being such a "giver."

You might be able to talk him out of this woman, but the exact same thing will happen with the next one. imho your best bet is saying what you said in these posts and suggest he find a good therapist. He needs to get his own **** straight...

at his side,..
eye to eye..
you keep talking about him being your friend and all that..
act like one...
or get an early start on laughing at him now..

Rika

Robert, you did not lose a friend, he did.

Fred, you have to try, or you would not have started this thread in the first place. At the end, you regret the things you did not do. You will regret it if you do nothing, even if it does not help.

"Then he'll get passive-aggressive since he's getting stomped on despite being such a "giver.""
~~~~~~~
An enormous amount of resentment from "givers" when their neurotic gestures are not reciprocated.
After all, altruistic givers usually give to get.
BTDT. 20 some years ago, I found myself in a give and take relationship.
I gave and she took.
Took me a few years to unravel that psychological whore's nightmare. :eek:

So we have an older, lonely guy who's tired of being alone who's marrying someone who might not be a good match? How many of you married the girl of your dreams, Camelot-style, complete with the white dress and cans rattling behind your "Just Married" car as you drove away in front of a hundred people? And five years later, you were left holding your nuts with half the bank account you had before. Part of the deal when you get married should things go south.

Yeah, stuff happens - you don't always see it coming. I've never gone through divorce but I've seen it a few times. Life is life - let him skin his knees and live his life. It works out it works out, it doesn't, it doesn't. As friends we mean well, but it's kind of silly to have a grown man tell another grown man who he should marry. The fiance finds out you meddled in their business you can forget about ever having a relationship with him when/if they get married. There isn't anything you can tell him that he doesn't already know.

IMHO, it doesn't sound like he was really that good of a buddy.

Best mates stick together no matter what.

id add #6: if she has ever taken away sex as a way to win.

Good point.
However, the fundamental purpose of an intervention is to let the person know that you care for them and as a result of that care you would like to see them alter their behavior...for their own well being.
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I've always thought that there's somewhat of a selfish motive for the one(s) who intervene because it seemed to me that they were saying, "You know how you are? Well, stop being that way because it causes me discomfort."
I can go both ways on this...not an easy one, for sure.

Your buddy has low self esteem,and adding another person to "cure" that won't fix it.
That is an inside job
The girl he wants to marry is an egomaniac, with low self esteem.
Really bad combination of people.
Take Rika's advice and sit him down and look him square in the eye,tell him honestly how you feel. Tell him if he moves forward, you will support him as best as possible.
Then prepare for the worst.

I say talk to him. Now is the best time given the recent weird behavior on her part. "I know it can suck to be alone but it's better than being unhappy with an evil person". "You need to work on your self esteem". "It won't get better when you are living and married to someone who will chip away at it every chance she gets". My guess is you'd lose him as a friend anyway if he marries her. She sounds very controlling and that will include who he hangs out with and when. Show sympathy, tell him you care, show him this thread maybe. I know what it feels like to feel like **** about yourself. I was there at my divorce in 2007. It's gotten way, way better since that point.

Seriously guys...all we know is that she looks like she was once hot (which means she is probably still pretty hot for her age), drinks (which an awful lot of hot women do) and was annoyed that this guy wants to marry her but wants a prenup. I can't say as I blame her. Clearly he already has reservations about "till death do us part". Unless this guy is a trust fund baby or a "catch" for some other reason, it sounds like she brings as much to the table (hotness) as he does. As soon as she is not "hot"...will he dump her like a hot rock for someone a bit younger and hotter...leaving her where she started (minus hotness)?

Isn't that is what marriage is all about. Sharing everything and planning for forever? Planning the divorce before the marriage just sorta kills the romance.

do you carry car insurance?

"She just moved in with him 3 days ago. He gave her the entire upstairs, and he moved into the basement. I dont think they even sleep together. She is mean... she drinks , was probably hot 10 years ago, but looks are fading, and she is looking to latch on to something."

I never had to move to the basement when my wife and I (26 years in July) moved in together,
this sounds more like an "arrangement" to me.

"I want half Eddie."

My friend got divorced a few years back (I posted here about it)

He got a real good lawyer, they lived together for 15-20 years, bought a house together.

She walk away $25,000

Did I mention he had a real good lawyer?

So the "she gets half" isn't always true.

I was going to say no, as he wouldnt listen anyway. ...but based on the comments above, I would actually agree that you're probably going to lose him as a friend anyway because women like that typically don't like friends hanging around for fear that they will tell him she's bad for him. So what have you got to lose, clear your conscience and hope he listens.

"She's mean...she drinks"

I just broke up with a "recovering" alcoholic. Most selfish, unreliable woman I've ever known. He needs to RUN!

respectfully:
i would not intervene.
it is none of your business.

Shoot him He'll thank you later