How can I get my brother to dump his gold digger girlfriend?

If your brother knows it and has dealth with it for 14 years, there’s not much that you’re going to say that’s going to set a light off in his brain about it. It’s obviously not a problem with him. Some relationships have little ‘agreements’ like this that they run on. They are both consenting adults and can have whatever kind of relationship that they like. Even if it is repulsive to people like us.

I think in this situation, you’d be better served to just ask your brother about the relationship. Ask him why he is in it, what he gets out of it. Understanding is the key to everything. Once you understand why your brother is doing this kind of thing, you may be able to tolerate/help more. You can certainly tell him your feelings–that you’re worried about him and being taken for a ride and you want to protect him. Whatever you do, don’t approach it with a “God, I hate your girlfriend, why are you with her?” attitude. That will just make him close up and get protective about it and you won’t get the info you want. I’d just say, “It seems like your girlfriend has a lot to offer, but is really swept up with money and material things you provide…how do you feel about that?”

People do what they want as long as they want. Until he sees how unhealthy his relationship is for himself, I’m afraid your stuck with dealing with it. 14 years sounds like he is in it for the long haul, though. So don’t get your hopes up that anything will happen anytime soon.