Dear Danielle,

I come from a very wealthy family. We have our own private plane and vacation homes in Maui and St. Barts. We don't need to work a day in our life if we don't want to, although we both do have our own careers. I am concerned for my sister because she has been dating a guy for about a year. He is a lawyer, but is just starting out and does not nearly have as much money as my sister. I have noticed that whenever I am out with them my sister always pays. Her boyfriend sometimes offers, but never insists to pay. I know she like to live the good life, and so maybe she feels responsible for paying for their lifestyle - but I think because he is the man he should still be the one to pay more times than not. In addition, they have been fighting a lot lately and I am worried he is just staying with her for the money. Should I say something to her about it? Or should I talk to him and tell him to start acting like a man when it comes to his relationship with my sister?

Sincerely,

"Protective Older Brother"


Dear "Protective Older Brother,"

Either your sister and her boyfriend should start doing less expensive activities, or he should fork over some cash to cover their lifestyle. If things keep going the way they have been, either her boyfriend will feel emasculated by the fact that she always pays, or he will start taking advantage of her and stay with her because of the money. It would be one thing if their relationship otherwise was going well, but it sounds like things are rocky and therefore the money issue definitely will come into play somehow. Speak to your sister and tell her you are concerned about her and want her to be with someone who carries his own weight, emotionally and monetarily in the relationship. Tell her that although it isn't necessary for her to be with someone as rich as you, whoever she is with must be generous with what he has. If she doesn't receive your advice well, back off quickly. Ultimately it is up to her to sort this out.