I don’t usually ask for advice anonymously, but I have a problem that I know a lot of women my age go through. After being married for 28 years, my husband decided he wanted a divorce. It hurt me, but I figured that since I’m still youthful looking, it wouldn’t be a problem for me to remarry.

That was five years ago. I discovered that for women my age, being single is a curse. Men who are around my age refuse to date me. The only guys interested in me are either senior citizens or men much younger. So, like a fool, I dated much younger guys. I suffered heartbreak after heartbreak. These young guys took advantage of me and my emotions. They said all the right things, promised me a future together, but they never had any intentions to marry me.

I swore off guys for a little while. Recently I met another guy, who is 11 years younger than me. This time I was smart and gave him a hard time about going out with him. I explained to him how I suffered from what other guys put me through. He promised that he is not like the others.

So we dated, and then the unexpected happened: He proposed to me. He actually wants to marry me. I said that I’d have to think about it. My children, parents, and friends are very much against my marrying him. They think that he is going to hurt me like the rest of the younger guys who chase older women have. They think that at this point I should just go out with senior citizens. They feel that an older man will appreciate me and treat me better. Are they right? I’m very confused.


By Baila Sebrow

Thank you for raising awareness of an unspoken and all too common dilemma. By publicly recounting your tale, you are bringing to the fore a situation that plagues older divorced women not just in the secular world, but in our frum society as well.

Regardless of the circumstances leading to it, divorce is devastating at any age. But when it happens at midlife, and after many years of marriage, the distress is further compounded by feelings of demoralization. At a time when many others are seemingly comfortable with their footing in life, the middle-aged person who was walked out on is left to pick up broken pieces of not just the home and family, but also the heart. Enduring a divorce and further experiencing rejection from men of one’s own age is an adversity from which few can emerge unscathed.

Those whose spirits have been broken remain emotionally vulnerable and consequently are easy prey for those who dare to take advantage of them.

That said, when the first younger guy showed interest in you, it is no surprise that you fell for every line he used to convince you of his sincerity. And when you discovered that the guy was not the gentleman he had portrayed himself to be, that was not enough to convince you that you might be the victim of a shameful ongoing phenomenon. That is why you tolerated other men similar to the first, and thus suffered the countless heartbreaks you speak about.

You are not alone in your circumstances. I realize that such knowledge is not enough consolation for what you have been subjected to. There are many women, in all hashkafic circles–from modern to chassidish and everything in between–who can confirm the truth of your experiences. And as I say to you and others in your predicament, it is not your fault. But, for your benefit as well as anyone else who might currently be involved in a similar situation, there are recognizable signs to be aware of.

Young men who deliberately hit on older divorced women not for the purpose of marriage usually fit a particular profile. Typically, these guys have been unsuccessful in dating girls their own age. They may not be able to deal with the pressures of competition from other guys who seek the same type of girl.

Many are also burnt out from dating and turned off by the entire system. Whether it’s a result of their singlehood or likely prior to that, many of these guys are not connected emotionally to their own mothers. As a result, they feel as though they are suffering from an emotional vacuum.

When such men purposely seek to date older women and convince them they have a future together when they really have no such intentions, they often do so as psychological redemption. They can finally prove to themselves that they are attractive in the eyes of women. Further, the age of the older woman represents authority, which only serves to add to the allure.

These types of relationships are usually a short-term experience. They are generally not dragged out like other relationships. Still, the pain of rejection cannot be minimized. That, along with the cold, harsh reality of being used, is crushing to the injured party.

However, not all guys who specifically seek out older women do so with ill intentions. Some are genuine and they just feel more comfortable with an older woman. These men find certain qualities in older women that appeal to them more than in the younger women they may date. These guys tend to be more mature than other guys their age, oftentimes as the outcome of a life experience.

As a result, such a guy will feel more at ease with a woman older than himself. Not only that, but he will also feel comfortable growing intellectually and spiritually. Some guys find that younger women are threatened by a man’s growth, even if positive.

As a shadchan, I come across men of various ages who have expressed that they would prefer to marry an older woman because they find that such women are usually more self-confident and less emotionally or financially dependent. And these guys are seriously marriage-minded.

I understand your hesitation in marrying this younger man who proposed to you. That your family and friends are against it is certainly no surprise. They witnessed your earlier calamitous relationships. They also watched as you dealt not only with the aftermath of a divorce, but also with the challenging reality that men your age typically seek out much younger women. And it is understandable that you in turn did not want to settle for someone you describe as a “senior citizen.”

In our culture, it is more common for a younger woman to date a guy around her own age or older. An older woman with a younger guy is viewed as a novelty–in the best of circumstances. Older women are theoretically off-limits for a younger guy. Yet no one bats an eyelash when the age difference is the other way around. If you were 11 years younger than the guy, then you would, strangely enough, have everyone’s blessings.

Bear in mind that your family and friends are concerned because of the abuse you experienced in being taken advantage of under the false pretense of potential marriage, so they feel that you might fall victim yet again.

Contrary to what your loved ones think, marrying a “senior citizen” is no guarantee that he will appreciate and treat you better than a younger husband. People are individuals, and age does not make one better or worse than the other.

I do not know how long you have been dating this guy who proposed to you. If it has not been that long, and you feel that you don’t know him well enough, then you reacted correctly by not immediately accepting his proposal. However, if your initial reaction is based on past hurts, that is not fair to the guy–or to yourself. You might be punishing yourself for the bad things other guys have done to you. Do not allow yourself to become emotionally caged.

Although you do not disclose your age, I assume that you are in the 50s age range. Nowadays a 50-something woman is not like the 50-something woman of the past. You state that you are youthful-looking. As they say, 50 is the new 30! This guy might not even consider you to be middle-aged.

Based on all that you are relating, I strongly feel that you would benefit from the services of a therapist. You are carrying a huge load of pain and my concern is not so much about whether or not you marry this guy, but rather your ability to move forward in life. You deserve all the happiness that you have been deprived of.

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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