Dude, you want to stay out of this if you want to keep that friend. All too many times I have seen friends try to "help" friends with girl problems. Most of the time, guy with girlfriend, will end up getting rid of friends who get in the way of his action. I'm sure you feel like you need to rescue your pal. You've done what a friend does. You've mentioned it to him, probably ad nauseum, and you've hinted to her about getting a job. Now butt out. Let hime either grow a backbone or learn an expensive lesson. It's his life, let him live it. If she catches on to what you are getting at, you will end up losing one friend and two players.