By Esther Mann, LCSW

This week’s letter is being answered by Jennifer Mann, LMSW.

Dear Jennifer,

I am what you may call a “distinguished” gentleman. By distinguished, I mean I am an “altakaka” in my late sixties. I have been divorced from my second wife for quite a few years now. I am constantly being offered to be set up by friends and family, and I usually go out. Even if it never turns to anything, I figure why not take a lovely lady out to dinner and see where it goes. Last summer, I received a text message from ex-wife number 1. Our conversations were stunted, taking several days to get to the point. For example, she would text me on Sunday morning, “How are you?” and I would write back Sunday evening, “Good, you?” A relationship this was not. But it picked up and I finally asked her why she started texting me. She told me she never fully got over me, always loved me, always will.

Back in my early twenties, ex #1 and I were married for about two minutes. More like two years, but it was fast. We never had children together; just got married too young and wanted different things out of life. She wanted a career, and I was a pigheaded chauvinist in my time and wanted her to stay home to raise children and cook my dinner. I have since changed. My second ex is a brilliantly successful career woman and I always supported her in every way possible. I have been accused of being a young ignoramus, which I think is mostly true, but everything worked out for the best and I can’t say I have any regrets because of what the future had in store for me.

Both ex-wife #1 and I moved on and married other people. Unfortunately, my second marriage ended after more than 30 years. I have beautiful children and grandchildren and have lived a beautiful, full life filled with simcha and nachas beyond my wildest expectations. Ex #1 was married, and also has children and grandchildren. Unfortunately her second husband passed away several years ago. She is actively pursuing dating me and I am not sure what to do. Do you think I should give this a try? Or do you think it is unwise to dig around in your past for a future love? Should I let a sleeping dog lie, or can you teach an old dog a new trick? What do you think?


An Altakaka at the Altar?

Dear Altakaka at the Altar

I certainly can’t tell you what to do, but I will answer your last question first with my honest opinion. You can teach an old dog a new trick! That better be the case, or I would be out of business! And teaching yourself is what I hope life is all about. If someone has taken an honest, raw look at himself and decided some changes were in order, and took the necessary steps toward facilitating change, then that is growth, pure and simple–or what you might call “a new trick.”

Growth is a beautiful thing. From your letter, it seems as though you are a different man than you were in your early twenties. You had grown so much that you supported a brilliant career woman. Perhaps now, all the wiser and more mature, you may be well suited to entertain the notion of dating ex #1. Maybe you were not ready to have each other in your lives in your early twenties. You don’t mention any details of your second divorce. Hopefully you have processed and reflected upon what went south and what, if anything, you contributed to the demise of the marriage.

Thus far, you have not responded to your ex’s advances and they remain unrequited. Something has been holding you back. It could be fear of the unknown, questioning her motives or your own desires. Clearly, she holds a different rank from the other ladies you date. Perhaps you are feeling that there is a lot more at stake because you were once married, and that is preventing you from giving this a chance. I have no way of knowing. Above all else, now is the time to do some personal digging and ask yourself how her advances have made you feel. Are they calling up old ghosts? Perhaps you have been giving thought to your marriage to her, your marriage to your second wife, or existential questions about the meaning of love and life. Try to think about the specifics that have kept you from answering her advances.

You do not indicate in your letter if you are interested in ex-wife number one. You only mention that she is interested in you and clearly is pursuing you. I guess my first question to you would be, are you interested in her? Have you thought about what you want and if this is the right thing for you at this point in your life? Do you envision yourself remarrying? Or, do you see yourself casually dating and not ready to settle down? I think before getting involved with anyone (and this goes for everyone) it is a good idea to know what you want. Of course, a certain amount of flexibility (as in “Man plans and G‑d laughs”) should be your best friend. I would always encourage you to be open to different possibilities life may unexpectedly offer. Ultimately, though, doing a little personal inventory is crucial for you right now.

If you decide she is someone you would like to pursue, my advice would be to take things slowly. Ex #1 began round two casually via text, but more recently has expressed her readiness to commit to you. She told you she has always loved you and always will. I may be wrong, but it seems she is ready to jump right in and at the very least be exclusive.

It would be unfair of me to surmise whether your ex is truly into you or perhaps feeling lonely since her husband passed away. There would be no way for you to know this either right now, and that is OK. But it is only a good reason to take things slowly. Perhaps you can accept her invitation, or invite her out to dinner. That would really be the only way to see if this has the true potential of being a real relationship. Your impression of your ex is as a young twenty-something woman. Four decades have passed. She is in love with the young version of you. Though a walk down memory lane can feel comfortable and soothing, it cannot be the basis for a lasting relationship.

You two need to spend some time together and get to know each other as mature, seasoned adults. Ex #1 may turn out to be someone who should remain in the past–or the next great love of your life. You won’t know unless you begin to spend time together. Often, the greatest regrets in life are the chances not taken and the road not traveled. You have some thinking to do. Good luck!



Jennifer Mann is presently working as a psychotherapist at Ohel. She also works as a relationship coach and can be reached at 718-908-0512.

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