Dear Rabbi,

I have a question concerning how to explain my past marriages when I’m out on a date. I am 57-years-old and have been married four times. The first lasted five years. I was 19-years-old. The second lasted nine years. The third was a 15-year marriage and I became a widower. My last marriage (the fourth) lasted four years.

I want to be honest with the new people I meet, but I don’t want to scare off a potentially great spouse.

Can you please advise me?

-When Asked…


Dear “When Asked,”

I want to begin by saying that although it has been a number of years since you became a widower, I am sorry to hear of your loss.

When getting to know someone new, it is appropriate that we reveal ourselves layer by layer. It takes time to get to know someone and to develop a foundation. In other words, we don’t usually have deeply personal conversations with people that we have just met. While I am a firm believer in honesty, relationships have a rhythm, and each conversation comes in its time. It is not necessary to reveal all of your stories on the first date, or even on the second. Once you feel that there is enough intimacy and safety in a relationship to begin to share that which is personal to you, that would be the time to begin disclosure.

I am guessing that you are uncomfortable with sharing your marriage history, or it would not have come up as a question. That having been said, what is it that makes you uncomfortable? Many individuals have been married more than once. If there is something that can be learned from the divorces you went through, even through dealing with your loss, perhaps focusing on the lessons you learned will be of value to share with your date. All of those marriages have contributed to who you have become today. Focusing on the merit and value of these experiences can show your date your level of introspection and personal awareness, both of which are characteristics of a good mate.

I wish you success in cultivating your new relationship, and hope that it withstands the tests of time.

To ask Rabbi Damsky a question, email

Rabbi Robin Damsky is the spiritual leader of West Suburban Temple Har Zion in River Forest, IL,, and is co-author of Find Fulfill Flourish, a book to help you find a life of meaning, purpose and fulfillment, at
  1. I disagree with this advice. I think this information has to be disclosed before a first date. For me and many of my friends, this info would be a deal breaker.

  2. “I want to begin by saying that although it has been a number of years since you became a widower, I am sorry to hear of your loss.”——-

    I thought your above response very inappropriate. He stated he was married and divorced after becoming a widower. ALSO why not “condolences” for divorced people or don’t you consider divorce a “loss”?

  3. As a clinical psychologist and divorced woman, I was appalled by your advice. You are obviously not living in the current dating world. Your advice is not only wrong, it would cause serious damage down the road. You should retract it.

  4. I liked the advice-I think it gives both the question asker as well as the person who he will talk to credit as being the feeling/thinking or thinking/feeling and evolving creatures most of us aspire to be.
    Also remember-this is a rabbi giving advice.

    I am not sure what a dealbreaker is-but maybe a deal is not what most of us are after?

  5. Mike, people don’t usually offer condolences for divorce… i do think though that while detailed stories as Robin advised are not obligation on the first date, the knowledge that one’s been married before usually is pre first date disclosure if it’s a blind or internet date, and if the two met in person it usually will be first or second date discussion. but if the two meet in person that’s usually a conversation that’ll be organically woven in during early dating.

  6. I think if the person keeps getting married and then divorced there is something to examine because they are finding the wrong people- maybe important to work on perception- paying closer attention initially.

  7. I really believe that any and all things that could change the other person’s idea of wanting or not wanting to get started in a relationship, should be “disclosed” as early as possible in the relationship. First date to me would be perfect.
    Yes, he might feel very good about it, he might have a few marriages under his belt too… but shouldn’t he be the one to judge if this is what he wants now, BEFORE he gets more involved, and suffers more if they break up?
    Oh well, my 5 cents worth.

  8. I agree with everybody, incl. the miss rabbi.

    I think people should.

    And despites, I don’t think one should reject a man for a date bc he’s been married four times. Either he is rich, which can only be good, to attract four different females, or else his parents-in-laws find him a good match, which says even more positively that he is worthwhile. (The parents-in-laws pay for the wedding, and they only part with money and a daughter if they find it worth. If the guy is no good, and the chick still marries him, then they sit shiva over the chick. That’s how we play the game where I’ve come from.)

    On the other hand, if the guy is self-conscious about being austricized over many marriages, then he is right about that, either because of his experience, or because of a guilty conscience for running away with half the brides’ houses, or else because he encounters prejudicial judgmentalism like by the respondents of this thread.

  9. As a person who’s been married and now divorced for 15+ years. I am still single. I think the Rabbi’s advice is very appropriate as it is impossible to know and trust someone until you’ve been together several times. There’s no point in sabotaging a potentially great relationship with someone who understands that Life Happens. All of us have a past, and for most of us, it wasn’t really controllable. Life Happens — most people in this world are terrific — allow yourself a chance to love and be loved by the right person. None of us are perfect, and we owe it to ourselves to at least listen to our stories. BTW, I’ve been engaged twice during the 15 year divorce; neither felt 100% right, and I didn’t want to divorce again. But I think people who Try are brave.

  10. What’s interesting is people are not reading this letter properly. This man said his third and longest marriage lasted 15 years and it ended when he became a widower.

    Most psychologists and even on the extensive JDate profile ask if people are single, divorced, separated, or widowed. Few people ask somebody if they’ve been divorced; how many times. The assumption is once. If a person has been married and divorced 4 times in 4 decades this is significant.

    However, a man who’s never been married by age 57 who claims he wishes to be might be considered with the same amount or more skepticism. Never been married implies a confirmed bachelor to most people. Both situations put the man on the hot seat because in our culture it is still the man who proposes marriage most of the time.

    This man feels he has some explaining to do when starting over in the dating world. He will be misunderstood and treated with prejudice. He will. If he’s in touch with the choices he’s made in his life and emphasizes the 3rd marriage which seems like the most significant one–dating should get easier with time.

    Best of luck.

  11. Good point, Nancy: if a body gets married 5 times, gets divorced twice, gets widowed twice, and somewhere along the way he loses a marriage certificate and due to specific amnesia he doesn’t have a recollection of his life with the fifth wife… is he a man who is: Divorced, widowed, or confused?

    If I were him, I wouldn’t know what to put on questionnaires of agencies like jDate. Am I single? Who knows. Furthermore, in a rather vexing outcome of events, I would be subjected to very tricky questions by the tax department and by my Rabbinate.

  12. Well. I also think the condolences were wrong as he had another wife after becoming a widower. I’d look at the first marriage as “too young”. Really no problem. Second one – that would have to be examined a bit and then the third how unfortunate.. but I would have a huge problem with the fourth marriage. A) who wants to be a fifth wife? And b) who is this Odysseus so torn to divorce three wifes.. I would get seriously cold feet. Sorry.

  13. This advice is meshugah!
    A series of prior failed marriages is, and should be, a deal breaker for most women who are dating with the intent and desire of getting married. Three failures and one success story doesn’t produce a great track record. I’ve had men hide this from me and I break up w/them the minute this happens. Silence about a material issue is plain wrong.

  14. Confused…. I read the letter a few times, and nowhere does this specify if this person is male or female?… not that it makes much difference, this is a tricky and not easy situation, and one who dates someone with such history will just have to be a good judge of character/trust their gut, best of luck!

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