By Baila Sebrow


I have been in shidduchim for a long time. It hasn’t been easy for me, watching all my sisters and brothers, some of whom are younger than me, get married. I don’t know why it is so hard for me, and was not difficult for my sisters. We are not exactly gorgeous, but for them it went 1-2-3. And they got married young, too.

It did not matter to any guy what I had to offer. Because I sat around single for a long time, I am more educated than my sisters. I thought maybe that would help my situation, but no. The shadchanim all told my mother that the boys today want models. Some of those boys are not even good-looking!

I davened and davened, and I met a boy on my own. We really hit it off, and we get along. But it bothers me when he talks about other girls he dated who were gorgeous. He knows it bothers me, and then he says that he likes me even though I’m not gorgeous. That’s really “ouch!”

I know I’m not pretty, but I always hoped that the guy I marry would see past that and that I would be pretty in his eyes. That’s how it is with my sisters. Their husbands think they are gorgeous, and it’s really not so.

He is the first guy I’ve dated for this long, but how can I get him to see me the way I want him to? I am scared to break up with him, because I will never get such a chance again. What do you think I should do?


You say that you met this guy on your own, meaning that this was not a formal introduction by a shadchan who somehow convinced him to go out with you. Furthermore, not only did he go out with you once, but you are in the longest relationship you ever had. Clearly, he feels an attraction to you, or he never would have dated you in the first place; moreover, it is continuing. It may not be the type of attraction that you would like him to have for you, but it is an attraction nevertheless.

The issue is how his treatment of you is causing you to feel about yourself. As you have seen among your married sisters, beauty is no doubt in the eye of the beholder. Your brothers-in-law not only believe it, but that they are making their wives accept that they are the most gorgeous women in the world. And that is how it’s supposed to be. Husbands and wives need to consider that that the person they are married to is the best there is, and nobody else can measure up. If you look around, you surely see people who may not be what you would consider beautiful; yet, in the eyes of their spouse, they are second to none.

I don’t know what is going on in the head of the guy you are dating. It is possible that he is suffering from low self-esteem, and pointing out what he assumes to be your shortcomings makes him feel better about himself. That, unfortunately, is not unusual. I see this a lot; even women do this to men. There are beautiful women who have expressed to me that they don’t want to date a very handsome man, because it will make them feel more secure in the marriage if they are the more beautiful spouse. Other times, they feel safer with a less-attractive husband, not having to fear that another woman would try to take him away from her. With men, it can be the same, where they feel more secure in the relationship if the woman is less attractive than others. Even if that is what they want, after the wedding, there are spouses who will point out exactly what they find unattractive. You can only imagine the lack of shalom bayis in such a household. Marrying someone for unwholesome reasons and then pointing out their shortcomings is deviant, and one can even say that it’s being spiteful to their spouse. If the guy you are dating is doing that now, then you are getting a preview of what’s to come.

When people write to me, I usually get only one side of the issue, and sometimes only part of the issue. That is why I try to cover as many bases as possible, not only to be fair, but so that my response will serve to benefit everyone concerned. So I would like to suggest another possibility that may be at play here.

There is an old commercial where the wife asks her husband who is distracted and totally unfocused at the time if he thinks the outfit she is wearing makes her look fat. His response to her (and again, he has no clue what she asked him) is, “You betcha.” Although that was a satire, it’s true that insecure wives and women in a relationship will often set up the man in such a trap. In their mind, they think it’s the perfect time to throw out such a question. But it is unfair because the answer he is giving her is not what he would have responded in a different setting.

And then there is the common circumstance when a woman will ask her husband or the man she is dating about his previous relationships. Again, this usually comes from a place of insecurity. A woman may feel an urge to compare herself to women who were previously in the man’s life. It’s a dangerous place to go, because the honest answer the man may give will feel hurtful to the woman and make her believe she is inferior. Sometimes, it’s not just a question, but a full interrogation. No one should ever do that! If a man is dating you or is married to you, and is treating you with love, kindness, and respect, believe that he is in it because he sees in you what he has not seen in others, whether it’s a physical component or that “beauty is skin deep.”

When a man who is in a relationship contacts me about such a predicament, I typically advise him that if the woman asks him how she looks or about other women, she does not necessarily want total honesty in hearing that others were beautiful. The woman wants to hear how she is more beautiful and better in every way than any other woman previously in his life, because it can stem from curiosity, too. People oftentimes want to know why they were chosen over others. There is also the issue of men who, while in the woman’s presence, stare appreciatively at other women. Although seemingly harmless, that can contribute to the woman feeling self-conscious and may cause her to question her own allure. Men need to be cognizant that they, too, want to feel special in the eyes of the woman in their life.

The most important phase at this juncture in your relationship is to find out whether the guy keeps bringing up past dates and how they looked of his own accord, or you are asking him out of sheer curiosity to see if he feels about you the same way your brothers-in-law feel about your sisters. If you are bringing up his past and asking him to compare you to others, then you need to let go of that chip on your shoulder and accept that he is with you because he wants to be there and with nobody else.

Specifically, because you met each other on your own terms and chose to date, I am inclined to believe that he chose you for who you are. It may have nothing to do with looks, and at times men and (also women) will choose somebody because of what they are used to in their own family. It is not uncommon to see that the wife looks like the husband’s mother or other female members in his family. Attraction is often misunderstood but should not be cross-examined either.

However, I want you to be sure that you are in a healthy relationship. I understand your fear that you may not meet another guy if this relationship does not work out, especially because you endured so many rejections while watching your younger siblings marry before you. That is the number one reason people have fallen into bad marriages. Please remember that if you attracted somebody now, you will attract again. The essential objective of your circumstances is to determine what is really going on.

Talk to him. Tell him about your painful experiences in the past, and that you feel hurt when he compares you to other women he dated. He might end up apologizing to you and will realize that your insecurities get triggered when he does that. It might bring the two of you closer together. You also need to be prepared for the possibility that he may end up putting you down. If he does, you can expect that it will progress to further abuse. It would then be in your best interest to terminate the relationship. You do not need to be in a marriage where you are constantly berated, G-d forbid.

No decent human being will deliberately want to hurt somebody, and, if so, there is a serious defect in such an individual’s character. Another thing: You make no mention of your hashkafic leanings. Frum daters are usually advised not to compliment each another. I feel that is a huge mistake. There are ways that a man and a woman can praise one another respectfully. If the guy is afraid to say something first, lest he be misunderstood, then if the woman is comfortable enough in the relationship, she can do that first and see if he follows. It helps to fortify the bond.

Now, I am addressing you directly. Young lady, you need to believe that you are beautiful. Beauty comes in all shapes, colors, and contours. Shame on anyone who told your mother that the boys are rejecting you because they seek models. Please tell your mother that in the future, she needs to tell such people that her daughter is a model. The next time you look in the mirror, believe that you are modeled exactly as Hashem wanted you to be. Hashem makes no mistakes, and all His creations are beautiful. 

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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