By Baila Sebrow

I am already a divorced woman at 23 years old. So even though I am pretty new to dating as a second-time single woman, for the last several months I’ve been dating a lot. My problem is that I can tell from the first date that the guy is not for me, but I keep going out with him anyway!

I am very good at these things. I knew that my ex-husband was a jerk from the first time I met him, but the shadchan made sure to tell everyone to convince me to give him a chance, and another chance, and then more chances till I was engaged.

I don’t want any shadchan to think that I am a waste of time, and not want to set me up anymore, so I continue dating even though I know for sure that no relationship will come out of it. Guys like me, because even though I am divorced, I don’t have kids, and I also date guys who are in their thirties, so I am on the top of every guy’s list.

The other problem is that I make such a good impression on the guys I go out with that they think I am interested in them when, in reality, I am not. I always feel like I am doing chesed when I go out again. I also always feel bad for the guy. How can I just say no after first dates without ruining my reputation that there is something wrong with me?

I have another question, too. My parents are divorced, and after they each got remarried, they both got divorced again. At what point should I tell a guy everything?

Before we discuss the marriage history of your parents, the bigger issue is the manner in which you are handling your dating process and how it impacts your life. The impression you are conveying is that whatever went wrong in your previous marriage was perceptively picked up by you about him on the first date. Yet, regardless, you continued to date him until you found yourself engaged and then married!

I am not sure why you think that the word “no” cannot be part of your vocabulary. Who were you afraid of offending? The guy or the shadchan? I will agree that there are shadchanim who take personal offense when someone says no to a shidduch they worked on, whether it’s declining a first date, second date, or impending engagement. There is a lot of work that goes into finding a shidduch for someone and bringing two singles together just to meet one another. And since shadchanim are not paid by the hour, or at all, there are those who feel that their time was wasted when someone declines an idea or the shidduch altogether.

However, that is part of being a shadchan. Lots of frustration and aggravation, sprinkled with joys here and there when a couple announces their engagement. Those who cannot handle when a client says no might need to reconsider shadchanus as part of their identity or job description and choose a different act of chesed that perhaps might come with more guarantees of success.

I am so sorry that you were compelled to continue dating a man you didn’t want—all the way to marriage. And though I will validate that your shadchan coerced you to keep dating your ex-husband, you need to take some responsibility for marrying him. There must have been some endearing quality about him that encouraged you to proceed.

I am saying the following with the greatest of respect. In order for people to succeed where they have previously failed, it is helpful to do some self-introspection and see where they might have made a mistake, what they learned from it, and how they can avoid making the same mistake again. It is not easy to do, but the benefit of such an exercise is that it can be done privately, within your own thoughts. If you find that you are unable to achieve any results, then, if you have not already done so, it would be a good idea to find a therapist who can help you.

It is possible that when you hear that a guy wants to date you, you immediately accept for another reason that is frequently seen in frum circles. That’s because getting a “yes” from a guy is not as standard as in secular circles (even though you do get many, according to what you say), where people are more relaxed about dating.

The next time you are suggested a date, I recommend that you do your due diligence and find out as much as you can about him, which may save you from future problems. The advantage also is that you will be declining fewer second dates, and, as a result, you won’t have to worry about offending a shadchan. Don’t worry about the guy. I doubt anyone ever had to nurse a broken heart after just one date that didn’t go any further. And even if it turns out after several more dates that the guy is not compatible with you, it is still OK to say no. You have that right, as much as the guy does!

At the end of your letter, you touched upon the topic of your parents’ divorces. Although it should have little bearing on your dating life, in many frum circles, it does. Even though the stigma of divorce has been reduced from earlier years, there are those whose families are intact who may act as though they are on a higher madreigah. We are now seeing a tremendous increase in divorces between older couples. People who have been married even 30 years or more are splitting, and when asked why, they say that they held out together for the sake of their children’s shidduchim. How sad that they lived miserable lives, denying themselves happiness while deceiving another family into assuming they are just like them.

According to your letter, your parents got divorced, they each remarried, and then they got divorced again. I can understand your concern. As a shadchan, I will tell you that although divorced parents are not acceptable to every family as their mechutanim, if they have remarried, it softens the circumstances of divorce. As both of your parents are twice divorced, I’ll tell you honestly that some guys and their families will not be too happy about it. Should you tell them right away? The answer is yes and no. You most certainly need to tell the person who is suggesting a shidduch to you that your parents are divorced. That would be for your own good, as it will weed out anyone who has a problem with it. Better they should decline before you get involved. However, there is no reason to give a detailed description about your parents and the story of their lives. It is more than sufficient to just say that they are divorced. If you date a guy for a few times and you start to feel at ease, then that would be the time to share that fact with him.

When you say that you make such a good impression on your dates that they think you are interested in dating them further, are you deliberately doing that? Meaning, if you know that the guy is not for you after one or two dates, why do you give them the wrong impression? Is it because even though you may not want to date them again, you need the reassurance that they find you appealing enough to want to go out with you again? If you are using that card to raise your self-esteem, please stop doing that. No good comes out of using anyone, even if it is subconscious. This is where self-introspection will come in handy.
Though you are still so young, you have been through more than many who are older than you. But with your pain and life experience, you have gained much wisdom and open-mindedness in your youth. And that is evident by not restricting yourself to only dating men from one specific age group. I am confident that with a little tweaking of your dating practices, you will soon reestablish your life as a married woman again.

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 Read more of Baila Sebrow’s articles at


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