Dear Matchmaker Rabbi:

I am living with a man who was in a 20-year marriage. We both are separated (me for 3 years and he for 1.5 years). We are both nearly finished with our divorces. We met when he had only been separated for five months. I have been dealing with issues with his older children, struggling with insecurities and adjusting to this new life.

The tension with adjusting to his older kids, and my five-year-old child, has put a toll on our relationship. Recently, he said he feels trapped, like he is married again. He isn’t happy, and I’m not either. The problem is, we still love each other. Our compatibility is off the charts, except for the issues with the kids.

We are going to a therapist. He said he is willing to try, but I am terrified. I moved for him and have enrolled my child in a new school. I guess I am asking if there’s any hope? Can this be fixed? I am scared to death and love him so much.

— Divorce & Rebound


Dear Divorce & Rebound:

In a word, yes, there is hope. I do, however, worry that you rushed into things too quickly. I’m glad you are trying the help of a professional therapist; you need to give the therapy process at least six sessions before deciding it “isn’t working” or that the therapist isn’t a good fit.

I realize you moved locations and switched schools to be with this man. All the more reason that you focus your efforts on building your own social network and support system in your new town that is independent from this relationship. If things work out – great! But if they don’t, you need to have new friendships and support systems in place (for both you and your child) if it doesn’t.

“Love” is a wonderful thing, but love alone cannot sustain a healthy relationship. Building good communication skills with all members of the family, including the children, is crucial.

You have much more at stake than your boyfriend does. If you two have a toxic living environment, his “older” kids who are on the verge of adulthood can pretty much brush it off and move on. They have already been molded into who they will largely be as human beings.

Your five-year-old is in a much more vulnerable place. Your child’s entire emotional foundation and health is being formed right now (and in the next five to eight years). Better your little one grows up in a home that is peaceful, safe and loving with you alone than in a chaotic home filled with more people, but people who are angry and distressed.

I hope you are doing all you can to maintain your financial independence as you work on your relationship. Perhaps, for example, you and your child need to live in an apartment nearby, so you can repair your relationship with fewer external stressors?

Good luck.

— The Matchmaker Rabbi

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Joysa Winter, aka The Matchmaker Rabbi is finishing a book on her 15 years of dating misadventures called “Chasing Cupid: Tales of Dating Disaster in Jewish Suburbia.” Need help writing your profile, or dating advice tailored to you? Email to learn more about pricing and services. You can also read Joysa’s blog on Jewish and interfaith weddings, as well as other progressive Jewish topics, at
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