I am a 52-year-old guy and have been divorced for a long time because it was very hard for me to find what I was seeking. I have always looked for a woman who was not older than 36. I know it sounds like chutzpah, but I have not been attracted to women closer to my age. Not surprisingly, shadchanim refused to introduce me to much younger women (even though I look like 40).

But Hashem has his ways. A few months ago, I was zocheh to meet a beautiful 29-year-old woman who fell in love with me for who I am. I told her my age right off the bat and she did not care. Our relationship has gotten very strong, and I am thinking of proposing marriage to her. I am sure she will accept, but I am scared that after we have been married for a while, she might start having second thoughts, as she will observe other couples who are closer in age to each other.

My friends are encouraging me to get engaged to her, but my family is set against it. They feel she is a “gold digger.” I am not wealthy, but I make a very good living.

I am distraught and torn over what to do. This woman is everything I have ever dreamed about, but I am also afraid of getting hurt in the end.


By Baila Sebrow

It is not uncommon for shadchanim to receive requests from marriage-minded older guys who stipulate that they want to be introduced only to much younger women. Factors for such requirements might include an attraction to younger women, as in your case, or the notion that younger women have an increased chance for fertility, or–sadly–for some guys, the deep-seated need to display a trophy wife.

Although no one has the right to judge any person’s motives in their specifications as they search for a spouse, shadchanim simply do not feel comfortable suggesting a guy in his fifties to a woman in her thirties. I believe that their refusal, as you state, to introduce you to a woman under the age of 36 was based on the concern that a woman in her early thirties is likely to feel insulted when a guy who is in his fifties is redt to her.

Savvy shadchanim always ask their shidduch clients about the maximum age of whom they would agree to go out on a date with. While it is true that an experienced shadchan should be able to present each person in the most positive and marketable manner to achieve healthy “out of the box” results, some things can come off sounding a bit over the top. No shadchan wants to lose credibility and reputation in the eyes of the singles he or she represents.

But, as you said, “Hashem has his ways.” Baruch Hashem, what seemed to be against all odds, after all those long lonely years without a wife to share your life with, you finally found exactly whom you had been searching for. Instead of feeling like the happiest man on earth that this woman who is 23 years younger than you is likely to accept a marriage proposal, you are instead manifesting evidence of extreme dread with regard to the future of this relationship.

I understand your apprehension, as it is natural at this juncture in your relationship. Any major life change–even if for the better–can be scary. Although most people would consider you lucky to have achieved your goal, instead of embracing such victory you feel like running in the opposite direction.

You might be afraid that after finally getting what you want there is the possibility of losing it. Combining with your existing fear is the antagonistic reaction of your family. I am not sure why they feel this woman is a gold digger, since you have never proclaimed yourself to be wealthy. It is possible that your family finds it hard to believe and accept that a woman who is young enough to be your daughter, and who has been aware of your age all along, is in fact in love with you and interested in marrying you.

Since this is your life and future happiness at stake, I would not completely discount your family’s misgivings about your relationship with this woman. You do not indicate how you and she were brought together for the first time. But from what I gather, it sounds as though the two of you somehow met on your own. Since there was no intermediary individual to guide you, I believe you both relied on your own instincts. Ordinarily that would not be a problem. On the contrary, many beautiful marriages originated from such scenarios. But you also have to be realistic. You are 52 and this woman is 29. So it is not surprising that the authenticity of this relationship can be questioned–and will potentially raise the eyebrows of even the most open-minded person.

If everything you are describing about this relationship and this woman is accurate, without any embellishment, I am comfortable in encouraging you to cautiously go forward. But before you propose to her, enlist the help of your family to find out more about her background and her life before she met you.

Hopefully, things will check out positively about this woman. If so, the advantages of your family’s involvement in looking into her history will be twofold: It will help in their acceptance of your relationship with her and, at the same time, it will assist in alleviating your fears and reservations that are causing a setback in your marriage plans. As you and your family will feel more confident about this woman and her motives, your path to a storybook ending will likely be actualized.

Baila Sebrow is president of Neshoma Advocates, communications and recruitment liaison for Sovri-Beth Israel, executive director of Teach Our Children, and a shadchanis. She can be reached at v

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