One of my best friends has been dating this chick for the last 5-6 years (with a few short breakups in between). She's fat, useless, dumb as a brick, smokes like a chimney, alcoholic, manipulative, demanding and incredibly greedy & superficial. Looks-wise, 4/10 is being generous.

Buddy is as BP as it gets - talks a lot of shit, but zero action or follow through. Drives her around to weekly mani/pedi sessions, never leaves the house without her, lets her fly off to Mexico for week-long vacations with her girlfriends (one of whom I shortly dated some years ago - another loose nutcase). I'd be shocked if she wasn't regularly sucking Jose cock while she was down there.

At around the end of this past summer they decided to move in with her parents in order to save money to buy a condo. Her parents are fucking lunatics in their own right, and living with them isn't helping.

A few months ago he proposed. They planned a wedding and even booked a venue, but their finances (or lack, there of) dictated that wasn't going to fly, so they cancelled the big event and just plan to do a small ceremony. That was a bit of a relief, but doesn't fix the main problem: if he marries this cow, and knocks her up (they do want children), his life is effectively over. He's a good guy and despite his flaws & lack of backbone, a solid friend. I hate to see him on this path of self-destruction.

One of our mutual guy friends feels the same way I do. He's brought up the idea of us needing to do something several times.

I can't simply sit my buddy down and tell him what's up. He's guaranteed to shut down, get defensive, and our friendship will be effectively over. The idea of leaving him plugged in and letting him throw his life away doesn't bode well with me.

He's heavily invested and I think he needs to be slowly broken down and out of his delusions. What can be done? The only thing I can think of is separating him from the cow via "guy nights" or "guy trips," and slowly introducing RP concepts into random conversations, so as to push him towards self-enlightenment, so to speak. A warm-up, of sorts. Any other ideas?