I recently met a woman that I had dated 30 years ago in college, before I became observant. In the meantime, I dated other women but never got married. This woman and I have now reconnected via Facebook, and she wants to marry me.
She is perfect in every conceivable way except one: her looks. She is older and looks it. Also, she found out three years ago that her father is Jewish, and she is now converting to Orthodox Judaism. I think she is doing that because of me. It’s really only her looks that are the problem. She is smart, wealthy, kind, etc. What do I do?
By Baila Sebrow
All living things undergo metamorphosis. While humans do not change as drastically as a caterpillar that turns into a butterfly or a tadpole into a frog, nevertheless, time, age, hormones, and health will alter the appearance of a person. And there is nothing we can do to stop that from happening.
I have no doubt that this woman changed in 30 years; she no longer possesses the youthful appearance that initially attracted you. But I will clue you in to a reality of which you and others of your mindset have zero inkling. Regardless of what you interpret in your reflection as you stare at yourself in the mirror, the harsh reality is that you don’t either look like you did 30 years ago. No one does.
Based on your account of having been in college 30 years ago, it is safe to assume that you are at least 50 years old. That makes both you and this woman middle-aged. It seems like you cannot deal with marrying a middle-aged woman even though you were born in the same era as she.
One of the chief complaints that shadchanim vent about is how middle-aged men request that they be set up with much younger women. There are some guys who claim that it is specifically because they want to have children, while others categorically state that they are not attracted to women their own age. Some shadchanim, in their zealousness to assist their clients, regardless of how unrealistic their demands may be, will contact women who are in their thirties and recommend guys to them who are in their fifties.
Some of these women in their thirties have even been suggested to men in their early sixties. The consequence of such actions is that, more often than not, the women get insulted and, as a result, start distrusting the dating system.
For the most part, however, younger women typically say no to a much older guy who is suggested to them. Do you know why? Because they are turned off by the idea of dating a much older guy.
I have always maintained that a shidduch is a personal decision, and each person has the right to reject that which is not appealing to him or her for marriage. So if this woman turns you off because of her looks, you are entitled to that opinion. However, my feelings are that if it were just that, you would not have written to me about your situation. You would have plainly rejected her, as I am sure you have done before in your dating history.
It does not sound like you are seeking validation for your decision, either. Rather, I believe that deep down you might feel that she is the right woman for you, and you are not sure what to do about those mixed feelings. So let’s examine this relationship and brainstorm about the best way for this to culminate in a happy ending for you.
When you met this woman 30 years ago, she was a college student. At that time, she must have been smart, but today she is certainly even smarter. You mention that she is wealthy. That is something which she likely accomplished over the years. That, along with her kind disposition as you describe, should qualify her to make a great spouse.
Although physical attraction is certainly not everything in a marriage, there does have to be that certain element of excitement for the person you are hopefully going to spend the rest of your life with. So unless you are willing to put that aspect aside and focus on the qualities that are pretty much everything in a marriage, you cannot, in fairness, continue dating this woman.
There is something that bothers me even more. I am worried that this woman is converting to Judaism for you. So devoted is she to you and your rediscovered relationship that this woman might feel compelled to give up something so major as her religion and set herself upon a path that will likely be very difficult for her.
There is much to be said about the halachic ramifications of her endeavor, and I will not even attempt to go there. I strongly urge you to speak to an Orthodox rav about this matter–and, more importantly, insist that she do so as well. If you are looking for a way out of the relationship, you can certainly utilize her current non-Jewish status as a good reason. You can explain to her that you have had the opportunity to study halachah over the years since becoming observant. There is no question that she will feel hurt; however, it should at least spare her feelings about the lack of physical attraction you feel towards her.
If it turns out that this woman is serious about Judaism and her desire to convert has nothing to do with you after all, then you still have a problem. She may go through the full process of geirus, and if she is still in your life, even as just a friend, then you will have to deal with the situation of your mixed feelings towards her.
I will reiterate, do not even consider anything further if this woman is converting for reasons other than her commitment to living a frum life. And only after all halachic requirements have been satisfied should you take the following advice.
If you are serious about wanting to get married, then you need to be realistic about life, and take stock of what you are bringing into a potential marriage. You, too, are not the same as you were many years ago. That said, from my experience in witnessing marriages of great age difference, there are issues these couples deal with that are not visible to the public.
Do you know how many older guys who married much younger women complain that during any argument, the wife always mentions his age? I know that it appears encouraging to guys when they hear of a much younger woman marrying someone older. But in these situations, there are oftentimes things said behind closed doors that are quite hurtful.
Whether it is this woman (after geirus) or someone else her age you might meet, I urge you to consider looking past the loss of feminine youth, and try to focus on the woman who will devote her life to you. There are times in life when a person marries someone who starts off looking good, but that is not what sustains a marriage. When chas v’shalom something goes wrong, a marriage that started for the right reasons will continue to flourish.
A happy marriage is shared only between two people who are faithfully committed to making each other happy above all else. And that is what I wish for you.
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
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