Ask Amy: Multi-Divorced Man Wonders How to Date

By Amy Dickinson | May 5th, 2021

Will any woman be willing to see past the four previous marriages?


Multi-divorced man wants to meet a wife Image

Dear Amy: I am in my mid-50s and have been married four times.

I am a recovering alcoholic and drug addict.

For 35 years, I abused substances.

But I have been clean for three years now and my life today is beyond my wildest dreams.

I have repaired the relationships in my life with family and have built solid friendships today with people I have met in recovery and at work.

I attend church and am a completely new person.

My old life was dark and suicidal, but my new life is beautiful and positive.

I have done a lot of work on myself, with the help of therapy and AA.

I believe I am the best version of myself today, however I am concerned with people judging me by my past life.

How do I start dating and explain four divorces?

Who would want to take a chance with a guy with such a turbulent past life?

Do I bring this up on a first date? Do I wait to be asked?

– Stormy Past


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Dear Stormy: Congratulations on your continuing recovery. It is truly inspiring.

You’ve already persuaded four women to put their trust in you, over the years. Now you just have to figure out how to do it, sober.

The way to date is to start doing it! Tiptoe into the shallow end of the dating pool, with the help and support of your sponsor and sober community.

Coffee dates and/or lunch are the current standard for meeting new people.

If your date chooses to drink alcohol, you should tell her that you don’t drink because you are an alcoholic in recovery. There. That’s one hurdle cleared.

Four divorces is not a first-date topic, in my opinion. Your first date should be devoted to covering more superficial basics and doing a lot of listening.

You have every valid reason to take things very slowly. Additional drama may be an unhealthy trigger.

If you are contemplating a deeper relationship, you should tell her, “I have a very challenging relationship history, and I think it’s only right for me to tell you about it, so you can make your own choice, with your eyes wide open.”


In the tradition of the great personal advice columnists, Chicago Tribune’s Amy Dickinson is a plainspoken straight shooter who relates to readers of all ages. She answers personal questions by addressing issues from both her head and her heart. A solid reporter, Dickinson researches her topics to provide readers with informed opinions and answers. Ask Amy, P.O. Box 194, Freeville, NY 13068

© 2021 by Amy Dickinson

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