I have a question that is different from most. My daughter is a straight-laced girl. She has been dating what seems to be a nice, good-looking, professional boy. He comes from a stellar, affluent family in his community. His parents are involved in all sorts of chesed.

When the relationship between my daughter and this boy became serious, my husband and I were thrilled to be meshadech with such a mishpachah. That is until someone made us face the truth about something.

We were told that this boy had a criminal past when he was a teenager. At first, we didn’t believe it. But then we checked into it further and found out from various reliable sources that it is true. We also found out that he had been arrested.

My daughter is devastated, because she really likes this boy. He is everything she is looking for, and she does not care about his past.

My husband feels that she should just break up with him and not reveal to him what we found out. My son-in-law says that “boys will be boys,” and as long as he is good to her, she should continue to date him. I think that we should at least hear him out before we make a final decision. How do you think we should handle this?


By Baila Sebrow

You need to understand that you are entering territory that you and your family are likely unfamiliar with. Criminal behavior, even though it might be a thing in the past, is still a serious matter. Your family and the people who love and care about your daughter are best advised not to take this matter lightly. There is a range of issues accompanying a criminal past, which usually carries lifelong consequences.

There are two types of teen offenders. One is the sort who begins to commit crime during his or her adolescent years and continues into adulthood. The other is the kind whose criminal career starts and ends in adolescence. While the latter sounds more like the boy your daughter is dating, you must understand that both types have a serious psychological foundation.

Teenagers who commit crimes usually fit the profile of an individual exhibiting antisocial or aggressive behavior. Even those whose lives of crime are a thing of the past–and have since grown into what may appear as productive adulthood–will still be prone to issues relating to mental health and substance abuse more so than those who have led a clean life.

My concern is that no one can know for sure if there is a possibility that this guy is masking his clean lifestyle. It might appear as though he is this wonderful boy, but secretly, he could be living a double life. Now you might say that this could also be the case of a boy who never did anything bad in the past. And you would be right to think so. However, it is precisely because he has a criminal history that you should be more apprehensive about such a possibility.

The deepest concern I have with this shidduch is if this guy is harboring aggressive behavior. If so, I fear that the day-to-day normal stresses of married life might somehow trigger him. Furthermore, you do not indicate the sort of crime this boy committed. Even if it was not of a violent nature, those who set out to commit a crime are prepared to do whatever it takes not to get caught. There are crimes that have ended in violence because the perpetrator panicked at the fear of being recognized.

My methods of advice always allow for giving someone the benefit of the doubt, except in situations where I feel that an innocent person could be placed in a dangerous situation. In addition, I am basing my advice on the notion that your knowledge about this boy has been established on concrete facts with no exaggeration.

I would err on the side of caution and not encourage a relationship such as you are describing to continue. I cannot advise anyone to encourage their daughter, and especially a girl who you say is straight-laced, to marry a boy who has walked on the dark side of the path.

The type of boy your daughter is dating might ultimately be happier with someone who can understand where he is coming from. Your daughter, although infatuated with this boy, has no clue what he is all about and how his experiences, vastly different from hers, have shaped him.

Commonly in these cases, the family of such a boy is under the impression that he would be best off with a girl who has a good past. There have been cases of marriages where a boy with a criminal past married a girl who has led an innocent lifestyle. The marital outcome of such situations has typically been disastrous.

Even though you do not state the nature of the crime committed, it sounds like it was serious enough for him to have been taken into police custody. That should immediately debunk your son-in-law’s myth of “boys will boys.” That slogan would work fine if you were to tell me that this boy was the class clown or acted out a bit by being rambunctious in his youth. A criminal past is a whole other chapter.

From the way you are describing this boy, it appears that he has been rehabilitated. Who knows to what extent? It also sounds like he comes from a supportive family who stood behind him during his trying times, which is probably one of the reasons that he is currently living a productive adult lifestyle, and is also a professional. That’s great for him. But you need to understand that the situation of an adolescent who comes from an affluent family, yet leads a life of crime, is more serious than you realize. For these kids, the explanation for why they commit crimes in the first place is almost always of psychological origin.

This leads to another important and disconcerting factor that you must also bear in mind. This boy comes from affluence, and there have been cases where that further complicated matters for the spouse who wanted out of such a marriage.

My first consideration is for your daughter and her feelings for this boy. It would be in her best interest to speak to a professional who can explain the consequences of being married to a boy with such a background. She also owes it to herself and the boy she is dating to reveal the information she has become privy to. We do not know where that will lead. He might convince her that his criminal life is a thing of the past and to focus on their future together. You also need to understand that she cannot suddenly turn her feelings off for him just because of new information that was discovered. She may still see him for the way he initially presented himself to her and how the relationship evolved.

You might have to accept that regardless of the people you contact to assist in convincing her that this boy is not a good choice, she might still insist on continuing this relationship. And if that is the case, you, along with your husband and the rest of your family, will have to remain close with her. Under no circumstances should you ever threaten to distance yourself from her. That will only force her to stay put in the relationship, even if she does pick up negative vibes along the way.

If it turns out you are successful in getting her to see this relationship through your eyes, then you and your husband have an obligation to this boy and his family. And as you suggested, it would be the correct thing for you and your husband to also hear him and his parents out. Give them the opportunity to share or deny anything about the past.

Throughout the conversation, you must treat them kindly. Compliment them on the fine young man this boy has become. Explain why you feel uncomfortable in having this shidduch continue. Be considerate of their feelings when they vent their frustration or anger.

This is a painful episode for both sides of the family, and even more so, for your daughter and this boy, which is why it is important that they both have a healthy closure should this relationship end.

Your daughter will need time to heal. Give her the space she needs, and at the same time, be there for her when she reaches out to you.

Baila Sebrow is president of Neshoma Advocates, communications and recruitment liaison for Sovri-Beth Israel, executive director of Teach Our Children, and a shadchanis. She can be reached at v

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