I'm not really stressing about this guy being supported by his mother. I realize that it doesn't affect me at all. Though I do think it's pathetic, and to those of us that have achieved success and financial independence through hard work and education, it's a little frustrating to watch. I included some of that info just to pain a picture of what kind of epic loser I'm dealing with here.

Ultimately though, it does come into play, like the example I gave about money to go to NY. Those kind of spats between he and his mother arise ALL the time, often in front of my kids.

Realistically, he's got some problems. He has some learning disabilities, and he did grow up fatherless. I understand that's led to some complications in his life, but he's almost 30, it's time to overcome. My wife has alot more sympathy though, and that's what REALLY complicates this situation.

There is an obvious answer here: He threatened me and made raunchy comments to my wife, I'm pretty sure there is a protocol that says I get to pound his gigantic nose through the back of his big boney head. Right?

Unfortunately, that approach is garaunteed to create a whole new set of problems between me and my wife. She's not willing to see things as black and white as I do. Her mom is old, and her brother is the only other family she has. So just cutting him out of our lives is not really an option. Especially now that he's sort of got his act together, it's a tough sell.

I'm kinda wondering how exactly I can make it clear to this dude that he's on SUPER thin ice, without causing a big scene.