By Baila Sebrow


I have never been married or engaged even though I am in my thirties. I always had this thing about not dating anyone who had a broken engagement, and for sure not anyone who is divorced. Shadchanim have tried to redt me to guys who are divorced, and I told them that there is no way that will ever happen. But it was getting harder to find a guy who has never been engaged or divorced, and I was starting to get used to the idea of dating a guy who had been engaged before.

I was introduced to a guy who I was told had a broken engagement. After our fifth date, he told me that he was actually engaged three times, and one time he broke it off very close to the wedding. He told me that it was his decision to end it so I have nothing to worry about. He told me what was wrong with each of those people he was engaged to. He also pointed out to me how everyone is getting engaged and breaking up. It’s like the “in” thing to do!

I really love him so much, but my parents are dead-set against my marrying him. Now I’m seeing him secretly.

He is so different from all the other guys I ever dated. He is perfect in every way. If I had to describe the dream guy, it would be him, but my parents won’t even give him a chance and get to know him. Why should I break up with the guy I love just to make my parents happy?


You have more than one problem here. It’s not just about your love for a guy you and your parents don’t see eye to eye about. Let’s first talk about his three engagements. He is attempting to convince you that he’s a great guy, because it was his decision to break up? That alone should raise a huge red flag. Why was he engaged three times? Does he have commitment issues and get cold feet at the eleventh hour? Is he an impulsive person? Perhaps he’s an intolerant one? That he made the decision to end it each time does not exactly place him in a good light as he is trying to imply to you. I would much rather he say that he made mistakes in his past relationships and that he learned from them. I’m not too happy that he was engaged three times or that he waited until the fifth date — when he was sure you were smitten with him — to tell you that. And it does not sit well with me that he takes no responsibility for anything that went wrong in those relationships.

I could suggest that you do research to find out more about what happened, but it is sometimes easier to find out why a couple got divorced than why an engagement was broken. Since they were never married there is little impression, if any, they may have left on those who know them.

What troubles me the most is his cavalier attitude about broken engagements. Despite the misinformation he is spoon-feeding you, it is not the “in” thing to do to get engaged and break up. Yes, it happens, but it is not to be viewed as the latest trend. Besides, if he really feels that way, what makes you think that it won’t happen to you, too? How are you so sure that you won’t be the fourth kallah to add to his collection? Is he trying to convince you that with you it will be different because you are so special, unlike the others? If he is intolerant or if he has a short fuse, you can be suspicious of where you stand in the journey of your relationship. I find his viewpoint distasteful and inappropriate.

Here is what confuses me. You are forgiving three broken engagements, but you would be offended if a shadchan suggests a divorced man? I am not telling you to specifically go looking to date someone who is divorced, but each case is different and should be examined and judged on its own merit. Divorce is very common today, and maybe it’s happening for the same reason as the broken engagements, which have also become more prevalent than in years past. My point is that just as you would question the reason for a divorce, you should look into the reason behind a broken engagement.

I don’t question your seriousness about this guy in your life. Nor do I question his seriousness about how he feels about you in the present. Rather, I question how long you will remain that way in his heart before he moves on yet again.

While one can argue that an engagement is not a marriage, when a man asks a woman to marry him, he is making a commitment to her, and she to him when she accepts. They both have dreams, goals, and plans for the future they will build together. Most people who have endured broken engagements, regardless of who the initiator was, will feel a sense of loss and require a period of healing before they move on. Unless he is hiding his true feelings, this guy is demonstrating that he is either not in touch with his feelings or he is completely detached from his own reality.

I am especially concerned about the engagement that ended close to the wedding. That one, in particular, should have felt devastating to him. Did it ever occur to you to ask him why he ended it, or do you just take everything he tells you at face value? You need to ask him every question that pops into your head. And when you get answers, you will need to internalize what he tells you. You may get curt responses, and you will need to decipher their meanings and be honest with yourself. But don’t stop there. Find out what happened in the other two engagements as well by conducting your own investigation of his former fiancées. What type of women are they? How do they conduct their lives?

In the best of circumstances, even if it turns out that he was not at fault in any of those broken engagements, you should still be on high alert in your assessment of him and consider if he is prone to any impulsive tendencies in his personality and mannerisms. In addition, it is imperative to be cognizant of exaggeration in his manner of speech. That should help you decode truthfulness. Furthermore, you need to tune in and focus on the subtle signs to see if he consistently finds fault in others or cuts down their achievements, to determine if this guy is dealing with issues of self-worth.

These are many situations where parents disagree or do not approve of a child’s romantic relationship. In most cases, the motive is concern for the emotional and sometimes physical well-being of their child. Regardless of how mature a person might be, when it comes to matters of the heart, some of the most intelligent people in the world have lost themselves and gotten carried away in the whirlwind of their feelings. When that happens, it is impossible for that person to see the truth about the object of their affection. And that is where parents, or any other loved ones, need to step in with an objective eye on the matter and honestly voice their opinion. In this case, I have to say that your parents have the right to be concerned. And because they love and care about you, they are likely reacting harshly in their attempt to make you see things from their perspective.

I believe you are privately questioning aspects of this guy’s character and gestures. However, you are probably dismissing any doubts you may have, while viewing this relationship through rose-colored lenses. You are sugarcoating any shortcomings you might perceive because this guy seems to otherwise present the qualities you seek in a husband. In addition, you may find the smug and perhaps adventurous aspect of his personality attractive.

That said, you must know that regardless of who the person is, everyone places themselves in the best possible light while dating. Even if they have a past or background that they are not proud of, they will do whatever it takes to make the best impression. With his vast experience in relationships, he knows exactly how to push the right buttons in order to be appreciated by someone he may set his sights on. It takes an objective witness to see the facts as they really are.

Please do not go deeper into the relationship before making more inquiries. Whatever you end up discovering, please take everything into consideration. Do not, under any circumstances, make excuses for what you hear about him. If you find yourself in the position of having to build him up to others in order to make him seem perfect, then you know that this is not a good relationship for you.

I understand that you feel he is different from any other guy, and that he is your dream come true. But when something or someone appears too good to be true, that is usually exactly the case.

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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