By Baila Sebrow


It’s getting to that point in my life where I’ll need to do something soon. I’m a 37-year-old guy, and I date a lot. And when I say a lot, I mean I’ve dated a few hundred women of all kinds — never-married, divorced, widowed, Sephardim, Ashkenazim, you name it. And all ages, too — younger, older, and in all shapes and sizes. I usually break things off after a while. I’m afraid of getting divorced; everyone I know is getting divorced. And also, I was married for a short time. Every person I know who got divorced was happy when he or she first got married. Then they hate each other and get divorced.

Women love me. When I go on a date, I am always overdoing it, and then I regret it. I take everyone to expensive restaurants, because I know that’s what most women like. So when I break it off, they get angry.

I’m starting to worry, because I see that the good women don’t hang around too long on the dating scene. I’ve noticed that when a good woman becomes single again, some lucky guy always grabs her up! And they are usually not even the good guys. I see how men with terrible reputations get good women to marry them at high speed.


To help put your anxiety at ease about good women getting married “at high speed,” you need to know that there are no hard-and-fast rules when it comes to who “grabs” who first. In fact, there is no grabbing involved! If you want to say that there are persuasive men who will go after a good woman as soon as she is on the shidduch circuit, then, yes, he will usually get a date or two with her, or perhaps a few more. However, when the relationship appears to take a more serious turn, an intelligent woman will do her due diligence to find out all she can about the man before she allows him to put a ring on her finger.

You point out that men with “terrible reputations” get the good women when they become newly single, which probably happens because these women may not have done their homework and trusted a man by buying into whatever was verbally fed to them. Even in this day and age, there is much naiveté and gullibility where dating is concerned. Some people put more time into deliberating over a minor purchase than choosing their life partner.

However, to play devil’s advocate, it is possible that these men have straightened up their lives, so whatever they may have done wrong in the past has little bearing on their future with respect to marriage. And sometimes, specific personalities bring out the better side of someone, too. That’s why you can often find that a person who has been a bad spouse to one turns out to be a good spouse to another.

Your focus with regard to marriage should be only on yourself — not on how other people choose their dates, spouses, or when they decide to get married. You need to do what’s good for you. And that starts with self-analysis. That said, my questions to you are the following: Are you afraid to allow yourself to get seriously involved with a woman just in case you will end up getting divorced? Are your overindulging tendencies on your dates (which you later regret) a result of the fear of not being liked? Do you feel the need to over-treat your date so that she loves you (as you claim women do) and won’t be the one to reject you?

To a certain degree, being afraid of something can actually be a good thing if it means one needs to evaluate the situation thoroughly. Those who think deeply before they act on an important decision are usually less likely to experience failure. And where it relates to marriage, one cannot be too careful, especially when dealing with people who have a history of previous marriage, divorce, and relationships.

There are times when all appears to be great within the person’s character that one is dating, but other factors can come into play that will make someone run from a relationship. It can be a fear that you may one day disappoint the person. Meaning, you represent in a manner that makes you attractive to your date. However, that may not be who you really are. You might be able to put on a show for the few hours you spend with her, but you know that there is a different side to you. And if it should ever be exposed, that might frighten or turn her off. Think about that.

No one will disagree that the divorce rate is alarmingly high. Most people initially assume that their marriage will work out. When they agree to marry, most couples believe that they are a match made in heaven. Sometimes it is not until they live with each other on a day-to-day basis with no pretenses that they realize they cannot make it work, no matter how hard they try. It could be habits that are intolerable to a spouse, or perhaps one of them may refuse to put up with something. There are times that stressors outside the home can make their way into the marriage, which may also contribute to the fracture of the union — children from a previous marriage, in-laws, other relatives or friends, unforeseen financial obligations, etc.

But a great percentage of the cause for divorce early on in a marriage is because people don’t look at the big picture before they head to the chuppah. When it comes to matters of the heart, the most introspective and contemplative person has the capacity to develop tunnel vision. They go for what they see, what they will personally gain from the marriage, and society’s view of the person they are marrying. Oftentimes, the essence of the person’s being and history tends to be overlooked. It’s like the wrapping on a present. If you are so fascinated with the wrapping and do not even care to look inside to see if there is a valuable gift, you will find yourself with a wrapping that will eventually become insignificant to you.

For some men, regardless of age or life status, dating just a few women might be all they need to find the person with whom they feel comfortable sharing their life. For others, it may mean dating countless women from all walks of life, almost as you describe doing. And even then it might take a long time to finally reach marriage. One should not place a time perimeter on an important life decision such as marriage.

I usually recommend that people be open-minded and look outside their own dalet amos to find a spouse. But it sounds like you are going way overboard with such a way of thinking. Please reread all that you describe with reference to the types of women you dated. To me that comes across more like curiosity about various types of women, rather than an intention to date for marriage. Not only that, but you do not offer any tangible reason for why you ended relationships. It sounds more like you develop nagging doubts, or perhaps mixed feelings, about women after you date them for a bit. And instead of figuring it out, you run. That may not have necessarily been the worst thing for you if you are not emotionally ready for marriage. Marriage is a work in progress for its entire duration. And until one is ready for it, he or she is best off remaining single.

You mention that you were married for a short time, and you left it at that. Whatever happened to you in the past might be finding its way into every relationship you are starting. Is it possible that the reason you date so many different types is because you are trying to find someone who is just like your ex-wife—or perhaps someone the complete opposite of her? And when you find resemblances or dissimilarities, does it cause you to break up?

Here is what I recommend. If you have not yet made peace with whatever happened to you in the past, it is high time that you do. Whether you seek the assistance of a therapist or someone who understands your psyche, it needs to be taken care of before you date anyone else and leave her bewildered. After that’s been accomplished, you need to determine what is important to you in a spouse that could hold you stable in a marriage. You can make a mental list or write it down. The point is that you cannot aimlessly go around dating any female just because she is breathing and walking. Not only is that unfair to her, but you need to place yourself in a position to successfully move forward towards a new, productive chapter in life.

Baila Sebrow is president of Neshoma Advocates, communications and recruitment liaison for Sovri-Beth Israel, executive director of Teach Our Children, and a shadchanis and shidduch consultant. She can be reached at Questions and comments for the Dating Forum can be submitted to


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