I am a 28-year-old guy and I am dating a girl who is almost 21. My parents and I were not too enthusiastic about the idea at first, because she comes from a dysfunctional family. Her parents are divorced and she has been living pretty much on her own since she was 16 years old.
But, because we are an open-minded family, I dated her anyway. It turned out that we are crazy about each other. We have even exchanged gifts with one another. This girl is gorgeous, smart, funny, and sensitive, and she has a well-paying job. She has everything that I am looking for.
The problem is that she keeps in touch with guys from her past. She says that there is nothing going on now between her and these guys. The reason she still talks to them is that they helped her out when she was alone.
I told her it bothers me that she is involved with these guys while dating me. Even though I believe there is nothing going on between them, her relationships with these guys makes no sense to me.
The last time we were together, I told her that unless she ended her relationships with those guys, I will not be contacting her. I also told her not to contact me, unless she can tell me that she will never speak to those guys again.
That was five weeks ago, and I miss her. Do you think I should call her and overlook everything? My parents say that I should not. I don’t know what to do.
By Baila Sebrow
It is refreshing to hear a guy who comes from a secure family life being open-minded in dating a girl who had very little, if any, family stability. It is commendable that your parents did not stand in the way of this relationship despite initial reservations. While giving this girl her fair chance in proving herself to be the type of girl you have always wanted, you were also willing to overlook issues that others in your circumstances might not have.
It sounds like this girl is still dealing with a troubled past–and I am not referring to her being a child of divorce. Although many people automatically classify divorce in a family as dysfunctional, those who are well informed on this subject understand that it is not always the case.
With divorce being widespread, various resources were created to assist members of families who are going through the painful process. Children of divorce are therefore, for the most part, coping much better today than in previous years. That said, I am inclined to believe that the dysfunction in this girl’s life is not so much that her parents are divorced, but the fact that for whatever reason she felt compelled to be on her own during her formative years.
Living on her own from the time she was a child of 16 must have been traumatic. There was no one for her to turn to for the comfort that she was rightfully entitled to. At that age, she lacked the intellectual maturity to make healthy choices and correct judgment calls. And so, when she became acquainted with these guys, right or wrong, they offered her some sort of stability.
As much as she is the type of girl you always wanted and who possesses everything you are looking for, you also have to believe that you, too, provided her with security and hope for a happy future. Therefore, in order to make an educated decision, you need to understand her thought process.
When you asked her to do away with those guys, as odd as it may seem to you, to her it was probably like asking someone to give up a family member. Imagine if, while seriously dating a girl, you were told that the only way for the relationship to continue was if you gave up someone you care about very much. That is exactly what is going through her mind right now.
It appears that this girl does not have any acting relatives to speak of, and these guys are her only semblance of a family unit. She needs, as does every person embarking on the journey to marriage, to have people in her life who are proud of her growth and accomplishments and will be there for her. In addition, she feels grateful for their acceptance of her when she was at her lowest point. The way it stands right now, this girl must be feeling betrayed by you.
At the same time, you also have every right to feel disheartened by the relationships she has with those men. Most guys would feel threatened by it. You do not indicate the ages of those guys or their marital status. I am not sure if that would make much difference, because the mere fact that she still communicates with them is what seems to be the cause of this strife.
When you challenged this girl to not contact you unless she first rids herself of these guys, you must have been shocked to realize that they mean so much to her that she is willing to risk losing you. As much as you miss her, hold off before you make any fast moves in contacting her.
The most crucial aspect of this situation is for you to not make a bad decision that can potentially bring about regret. For starters, you need to find out who these guys are and whether there was anything within these relationships that makes you uncomfortable. If you do ascertain that something else took place–other than assisting this girl when she was in distress–you need to tread with caution. Even though this was a matter of the past, her communication with them in conjunction with a marriage cannot be healthy. I would then advise you not to reestablish contact with her, lest you set yourself up for future pain.
The other matter that should be of concern is whether this girl has any female friends that she is close with. In most similar circumstances, a girl will gravitate to an older woman for mentorship. If she has only had male influences in her life, that should raise a red flag in terms of how she views normal relationships.
But again, the focus here is the extent of her relationships with these guys. If it turns out that their roles were entirely of benevolence and support towards this girl, then the picture changes entirely. If you truly care about her and are willing to accept her tumultuous past, then you would have to acknowledge that these guys are to this girl as your parents are to you.
Should you decide to advance your relationship with this girl, contact her and explain why you felt initial discomfort and that you now understand why she took such a strong stand in defense of those guys being in her life. Emphasize that you feel better equipped to emotionally deal with a situation that you were not previously familiar with.
You must also be mindful to never mock, accuse, or act suspicious when she is around those guys. All you will accomplish by doing so will be to drive a wedge between you and this girl. At the same time, you still have the right to insist on healthy boundaries and sensitivity to your feelings as well. While in the past she may have been used to turning to these guys for any problem that came up, she must understand that now you are the man who wants to be there for her at all times. I will also advise you to gently encourage her, and offer to join, in visiting a therapist to talk about any issues from her past that may still be bothering her.
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
Questions and comments can be submitted to

Previous articleHirohito, Rav Aharon, And Truman
Next articleTake Comfort


Please enter your comment!
Please enter your name here