Samara O'Shea, love columnist

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



Dear Good Friend,

I know how you feel. Watching someone you care about enter into a romantic relationship with an unstable (to put it nicely) person is one of life’s more difficult circumstances. I’ve been there a few times and in every case I made it clear that I thought the incoming partner was bad news. There have been mixed results.

In one instance my friend told me she appreciated my point of view but stuck with the relationship—for a while. Ultimately, she saw the red flags herself and called off the engagement (hallelujah). Another instance was more complicated because it dealt with a male friend of mine who was dating a very jealous woman. I told him that I thought her unreasonable jealousy was a bad sign of things to come. He did not appreciate my insights and blamed me for causing trouble. Their marriage lasted 17 months. Our friendship never recovered.

Your friend can’t see what you see because she’s in an altered state of mind. She’s either head over heels for the guy, tired of being alone, or seeking financial stability. These emotions—infatuation and desperation—whether operating together or separately lend themselves to bad decision making.

You should absolutely tell her what you think. With compassion and concern, sit her down and tell her what you told me. Say it’s difficult for you to say but, as a friend, you feel it’s important.

You say, “None of us like him.” If there is more than one friend who feels this way, perhaps a group of you could sit her down. Be careful not to ambush her. Make it clear throughout the conversation that you are doing this out of genuine concern. If she gets defensive, which is likely, try not to take it personally.

Here’s the hard part: You should go into this conversation knowing that it’s unlikely to change anything. It’s still important to speak up. If a friend is drowning, we have to at least try to help. If they don’t take the hand we offer, that’s on them. Ideally she’ll thank you for your concern but reaffirm that she’s in love and moving forward with the relationship. Worst case: She’ll get mad and say a) You’re just jealous or b) You don’t want her to be happy. Brace yourself for these reactions and try to stay calm. Assure her that you do want her to be happy but you think this guy will do her more harm than good.

I recommend watching this TED talk—Select the Right Relationship—before you sit her down. This is a good primer. It will reassure you that you are doing the right thing by speaking up. After you talk to her, no matter what happens, send her an email reiterating that you want what’s best for her and you hope she makes the right decision. Include a link to the same TED talk and suggest she watch it.

There. You’ve done all you can do. I hope she will consider your point of view.


Good luck,




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* The ideas and advice presented here are not a substitute for professional advice. Talk to your psychologist, counselor, physician or health care professional for situations that warrant further analysis.

image by Emre Danisman