By Baila Sebrow


I am dating a guy who is much younger than me. He is a great guy, even though he is young. He is more mature than people double his age. He has a great job and lives in a beautiful apartment. Everyone thinks I’m crazy for dating him—until they meet him. Then they like him.

My parents were OK about my dating him until it started getting serious. That’s when they turned against him. My parents are against him because of his family and his past. His parents got divorced when he was a baby. His mother remarried and got divorced again, and his father was not around too much in his life. He did get involved with some bad friends and was kicked out of schools, but he really straightened up his life.

My main problem is not what my parents think. Rather, I am angry that he is still friends with the bad guys from his past. He says they are his friends and always will be. I can’t stand them. They are loud, talk dirty, and are really low-class. And they always hang out with us. I’m so disgusted.

The last time we were on a date, he brought up our future together. On one hand, I was so excited, but on the other hand, I told him that I would never marry him if he is still friends with those creeps. He said, “Don’t make me choose, because you will lose.” I started crying and he took me home.

He didn’t call me for a few days, so I called him. He told me that he loves me, but he will not be controlled by anyone. And if I can’t respect his friends, then I don’t respect him. He told me not to call him until I think differently.

My parents were happy to hear this and they are trying to get me dates with other guys by calling their shadchan friends. But I want this guy and I miss him. What do you think I should do?


You seem to have deliberately omitted the age difference between you and the guy you’re in a relationship with. You might think that it has no bearing on your story, but I am concerned. I am sure it is flattering to you that a much younger guy is dating you. Furthermore, his maturity is reassuring to you. But you need to realize that oftentimes those who have experienced challenging pasts and rise above it typically present as being more mature than others their age. For your own sake, you need to make certain that his intentions regarding you are coming from a levelheaded place.

Putting the age factor aside, I find it refreshing to hear how someone who originates from a secure upbringing and home life is tolerant and unbiased enough to date a guy with such a difficult past. From what you are sharing, he had no stability growing up, which further resulted in his involvement with questionable types of people who became his friends. Getting thrown out of school but becoming successful to the point that he is living comfortably is commendable and shows strength of character.

I find it interesting that your parents did not stand in the way of this relationship until it became serious. Did they assume that he is just a friend? Or did he give the impression that he is not the type of guy to get serious with you? And once they realized that he is thinking of marrying you, why did they suddenly become antagonistic? You do mention that people like him once they get to know him. So if your parents did get the chance to know him, they should be happy for you if you are happy.

However, you are not happy. You say that it has nothing to do with his past. Rather, your issue with this guy is that he is friends with people with low values in specific areas. And when you expressed your feelings to him, he told you that these people will always be his friends. That clearly indicates that his past is still part of him.

There are cases where people have had a troubled past and straightened their lives out. But in most of those circumstances, not only did they leave their lifestyle, they also left their friends. His insistence that they remain indicates that he most likely still shares much in common with them.

His friends represent family to him. From what you are saying, it appears that he has no one else whom he is close to that he can refer to as a family member. And so, when you asked him to give up his friends, it was as though someone would ask you to give up a sibling or parent. When such a request comes from the person you are dating, it feels painful. In his mind, he is dating someone very seriously, and the person he is considering spending the rest of his life with is making him choose between her and those he considers to be his family. In a way, he might feel betrayed by you.

But there is an even bigger problem here. His reaction to your feelings about his friends is characteristic of unhealthy communication. Instead of discussing the issue with you, he turns you into the aggressor, accusing you of controlling him. He is also letting you know, in no uncertain terms, that he is not giving up his friends, and if you can’t accept it, then it’s too bad. That is not OK.

I am not saying that you are right and he is wrong. On the contrary, you are both in the right here. It’s the manner in which he is reacting that I find off-putting. However, you are miserable because you feel that your relationship is now on shaky ground, and the bottom line is that you don’t want to lose him. At the same time, you also have every right to feel disheartened by the friendships that he has with those men and the fact that that they are so much a part of his life.

My question to him is when he challenged you to not contact him unless you are ready to accept the entire package (him and his friends), was he not afraid that he would lose you? Does he feel so secure about your feelings towards him that he thinks he can throw around threats that can sabotage the relationship you have with him? Or does he not care if the relationship ends as a result of those men?

In many marriages, there are people in the life of a spouse that the other spouse may not like or get along with. You can choose the person you marry, but there are people who have always been in your spouse’s life who just happen to join the union. Strife in a marriage and even divorce, G-d forbid, can happen because of a family member or even close friend that one spouse does not like or may disapprove of. It takes a confident and clever person to be able to accept that unwelcome individual while at the same time keep him at a distance. I will not tell you that it is easy, but it is definitely doable.

This guy has a sensitive spot for his friends. If his life is now as straight as you make it out to be, there is a strong possibility that he also disapproves of the way they speak, but he is not sure what to do about it. Not only that, but it is quite possible that once upon a time, before you knew him, his behavior mirrored theirs.

At this juncture, the most fundamental aspect of the situation is for you not to make a bad decision by saying the wrong thing that can potentially cause you to have regret. You first need to find out if these men are involved in any sort of unlawful or immoral behavior. If so, then the guy you are dating needs to recognize that he might get dragged into their mess. And if he won’t accept that, you will have to realize that it will become your problem too, should you marry him with those men tagging along.

If it turns out they live their lives as upstanding citizens, but their speech bothers you, that can be worked on if he is willing to compromise. You can tell him you understand that his friends are an important part of his life, and you will welcome them in your home, but the way they talk makes you uncomfortable. If you present it in such a manner, and if he cares about you, he should have no problem getting them to censor their speech, at least while in your presence and home. And if he needs more incentive, stress that you want your future children, iy’H, to be raised in a pure and holy environment.

Because of the way he lived prior to meeting you, he may have never had the opportunity to befriend people who are more refined. This would be a good time to include him amongst your family and friends. You say your parents are against him, but you don’t care. Try to get a rav involved. It is to everyone’s benefit when parents and in-law children have a good relationship, if possible.

I will also caution you never to make fun of his friends, as that in itself will be enough to drive a wedge between you and him. Be sensitive to what he has endured, and praise him for what he has become. Positive reinforcement goes a long way in building a happy home. 

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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