Samara O'Shea

Archive for February, 2016

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

Wednesday, February 24th, 2016

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.

Would You Give a Guy Who Broke Your Heart Another Chance?

Friday, February 5th, 2016

Hi Samara,

I am 42 years old. Divorced twice, no children, 1 dog. Recently, I reconnected with my high school sweetheart. He is divorced with 2 children. We are madly in love once again and I think I want to spend the rest of my life with him.

The problem is that we reconnected once before in our late twenties and it didn’t work out and I was terribly hurt by him. I see many positive changes in him since we started seeing each other again. This is the third time around with him. I am wondering if we both needed to grow up before finding each other again or am I just fooling myself?

Any suggestions on how to approach this relationship this time around. I really want it to work.

Thank you,

Check out my response here.