I've always been one of those people that has a TON of acquaintances and very few extremely close friends.  Just a month ago I graduated from Gonzaga University in Spokane, WA before moving here to Boise for 103.5 KISSFM.  While studying at Gonzaga, I had one friend that was closer to me than anyone else. He and I met during orientation our freshman year and were basically inseparable.

Here comes the plot twist.  Sophomore year he met a young lady and ever since, they've been dating.  I was never her biggest fan.  She tells her friends (and I'm paraphrasing) that she loves his financial situation and that she wouldn't have to worry about working much.  She's definitely been enabled by him and his family, so maybe I can't blame her TOO much.

Just last night he called me and said it was time to propose.  He sounded excited so I played along, but he made it clear I would be his best man.  Am I crazy for wanting to tell him maybe he should re-evaluate? He's my closest friend and from an outsiders perspective I really think he may be getting used. I don't even know if I could GO to the wedding!

Has this ever happened to you? What should I do??