Well, I'm glad it worked out for you Matt. However, I have a different take on this kind of situation. My advice would be to stay out of it and enjoy your buddy's company when you get a chance. Let him learn how bad she is for him on his own or it could backfire on you. When I was 21 or so, I was in the same situation with my best friend whom I'd known since age 10. I told him my thoughts about his girlfriend and he told her what I said. She told him he couldn't talk to me anymore and we didn't until his mom was tragically murdered about 5 years later. That was 6 years ago and, while we actually work together in the same agency, things are still a bit "off" between us in that he still remains incapable of making a decision or taking an action for himself if his now wife opposes it. Just my $0.02