Dear Matchmaker Rabbi,

I have been dating a man who has been divorced for two years but was married for 37 years. He said he wants to get married again, but he’s been hurt and has built walls up. Sometimes he is not dependable and seems to run from his feelings for me. He is just under 60 years old and I am in my middle 50s with no time to waste. What is your advice?

— In a Quandary

Dear In a Quandary,

I feel empathy for people who have built walls up and are afraid of being hurt. It’s totally understandable, and let’s face it, who among us doesn’t have baggage? I imagine you have your own “baggage” you bring to a relationship (if nothing else the fact you have been single for so long). Your baggage just happens to be different.

That said, you can’t sacrifice emotional intimacy in a relationship that is going to last. It will either sabotage the relationship, or you will be left to live with growing feelings of resentment — and hence, unhappiness.

The question I have for this guy, or for any person who claims to want long-term love but throws up roadblocks to truly having that, is this: How much are you willing to grow, and challenge yourself, to have a healthy relationship? Will you see a couples therapist with this woman to work on your communication? Are you willing to read relationship books and work through some exercises together?

If the answer is “Yes,” by all means it is worth a shot. If the answer is “No,” he doesn’t really want what he says he wants. He might want a “marriage,” but he doesn’t want a partnership.

— The Matchmaker Rabbi

To ask the Matchmaker Rabbi a question, email her at myrabbi@jdate.com.

Joysa Winter, aka The Matchmaker Rabbi, knows all about how hard it is to find lasting love. It took her 17 years to find Mr. Not Wrong! In that time, she tried just about every singles site, dating club and Matzah Ball known to humanity. Now a rabbinical student and the mother of 2 young kids, nothing brings her greater joy than officiating a wedding. She is finishing a book on her dating misadventures called Chasing Cupid, Tales of Dating Disaster in Jewish Suburbia. Read more about it at www.chasingcupid.com.
One Comment
  1. If a person lives in the past, is wasting your time and his, he did not knowingly destroys himself instead of a new build.
    Our very essence as Jews is growth and renewal, of life that we produce
    Overcoming obstacles that come our way yet to love the evil as good.

    For every person that comes to this site. Each comes with a different agenda,
    There really and truly want to build a new relationship and are willing to pledge, commitment is a ceremony which means the connection
    If a person lives in the past, is wasting your time and his, he did not knowingly destroys himself instead of a new build.
    Our very essence as Jews is growth and renewal, of life that we produce
    Overcoming obstacles that come our way yet to love the evil as good.

    For every person that comes to this site. Each comes with a different agenda,
    There really and truly want to build a new relationship and are willing to pledge, commitment is a ceremony which means the connection
    I wonder how a woman who dedicated her life and career had reached the age she was already ready to marry, can connect to one spouse – only tracks down the gauntlet

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