Samara O'Shea

A Good Friend is Dating a Not-So-Good Guy. What Do You Do?

Dear Samara,

My best friend is widowed and has been single for five years. She had some money, but recently lost most of it on a bad investment.

She has dated different men up until now and a few months ago met a man she is totally in love with and says they want to get married. The problem is, he is not a good guy—so says I. None of us like him, he’s sleazy and we’re wondering what he really wants from her. He has lived in the same area as us for a long time. We know him by reputation, he is not good with money, has had many girlfriends over the years and has been married once before. He has no kids. I know I am judging him, but why can’t she see what I do?

How do I tell her that she’s heading down the wrong road or does she have to find out by herself? If she does marry him I will still be her friend, but it will impact our friendship.

Good Friend Jen

Read my response.