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Dating Forum: Wary About This Relationship



I would love your professional opinion about my husband’s male relative. My husband and I have become very close to him over the years. Since he is single, we have been trying to help him find a shidduch. We have set him up in the past, and he is now dealing with a situation we don’t know how to help him with.

He was never married and is a ba’al teshuvah. He’s been through a lot with dating and is burnt out, which I can totally understand. He was introduced to a girl by a coworker at his place of employment. They’ve been dating for about a year. We always ask him how things are going with his relationship, and we keep pushing for him to pop the question to her. He is usually evasive, and the last time we pressed for information so that we can help out with advice, he told us some things that are very concerning to us about why he is not yet ready to propose to her.

He wants to marry someone who will cover her hair, and she does not want to. He wants someone who will not wear pants, and she won’t change that. She told him that when they get married, he can’t have his own bank account although she will maintain her own. He said that she’s cheap when it comes to buying herself things, but she wants him to buy her expensive things, including taking her out to only expensive restaurants.

Instead of feeling more strongly for her over time, he said he felt more for her when they first started going out, and he thinks that’s natural to happen. He said his rabbi encouraged him to continue. I feel that he’s headed into dangerous territory and I’m afraid he’ll get hurt. He is a great guy who deserves an amazing girl. I was wondering what your thoughts are.


There are four issues going on here. The first is that your relative and his lady friend are not on the same page hashkafically. The second is that they have opposing financial views. The third issue is that his feelings for her have changed. And the fourth is that the rabbi is encouraging him to go forward with the relationship despite his reservations.

I will start off by saying kudos to this rabbi. I don’t know if he is an old-timer or not, but the advice that he is giving is certainly not the trend today. So if he is a young person, then I double my kudos to him! As a shadchan, I mostly hear where rabbis are advising those with reservations of much less significance to break off the relationship. Their advice is based on the notion that the couple will just turn around and each will find another person as easily as snapping their fingers. Those in the shidduch parashah know very well that it doesn’t quite work that way. You don’t easily find a compatible person whose company you enjoy, and if you are looking for someone who comes with zero issues, that is like expecting 70-degree temperature every day in a four-season climate area. What typically happens is that the person is trading in one set of issues for a different set of issues, or they get so jaded they remain single for life. Gone are the days where people take the time to sit down and work through issues with the current partner in their life and learn to live together in harmony. I am glad to hear that this rabbi is of the mindset that you fix what you have rather than dispose of it.

With that said, let’s see how we can salvage your relative’s relationship. I want to focus for a bit on his altered feelings for this woman, which I think he realizes. But this is important to reiterate for his sake, and even for you to understand, so that you can assist him more effectively. When people first start dating and discover that they like each other enough to continue the relationship, they enter the infatuation stage. The feelings during that period are very powerful; it is the “honeymoon stage” of the dating relationship. The couple is on a high. But no one can remain on a high forever. At some point, you must come down to earth, and that’s when the problems begin and when people start second-guessing their feelings. This is especially common in couples who date longer than a few months. The familiarity sets in enough where they each let their guard down and their true colors show through.

Normally, that would be a good thing. It means that they are both comfortable enough with one another to share their true feelings about what they want out of life. Healthy, mature individuals will take that to the next level where they are able to discuss any differences or misunderstandings and work directly from that position. After all, when people are married, things come up in life and they may not always see eye to eye on everything. In a strong relationship, they will negotiate, eventually agree, or even agree to disagree in a harmonious manner. If people cannot learn to do that before marriage, what will they do when stressors sneak up on them after they are married? Get divorced? And then what? Marry and divorce again?

Your relative’s feelings for her have changed, as expected, and that would happen with anyone else he may date. As I implied, infatuation does not remain forever. In its place are two people who, if they want to make the relationship work, will do whatever it takes to make that happen. And if they master doing just that, respect and love will hopefully follow, and that is what cements the unbreakable bond between a couple.

Finances are a very tricky subject. The way one approaches money matters has much to do with upbringing, as well as how the person managed financially before entering into a relationship. Those to whom money came easy are usually laid-back and sometimes even overly generous to the point of being a spendthrift when it comes to purchases. Such people don’t know what it means to be low or overdrawn in their account. It is possible that this woman had serious problems with finances, where she might even be in debt, and that may explain her overwhelming need to be taken care of.

I do not agree that she should keep her own account to herself while he shares his with her. That needs to be addressed, as it is completely unfair. Nor do I agree that she be consistently indulged by being taken out to lavish meals at expensive restaurants. Then again, is that how he initially treated her? Meaning, I oftentimes find that, in their effort to impress their dates, men will go above and beyond their spending means on their dates. No one can keep doing that forever, so when the man goes a bit cheaper, the woman starts to worry that he is not as generous as she assumed. She might get the impression that he is frugal, when he is just trying to live within his means. But that is an issue he should be discussing with her, not you or your husband. He needs to explain his position to her, express his ideas about shared bank accounts, and hear her response.

Right now, you are concerned about him going forward with the relationship based on how he perceives the situation, but even he is unaware of all the details. And as well-meaning as you are, that might be doing him more harm than good.

I am leaving the hashkafic aspect of his apprehensions last, because that is the most troubling facet of what you have shared. How one chooses to dress from a hashkafic or halachic viewpoint may not be the biggest deal as a newly married couple. However, it becomes a major issue when children come into the picture. Will they both be on the same page where it relates to how the children will dress and where they will go to school? Yeshivas have their own dress codes that they expect every student to abide by. If your relative wants his children to attend a more right-wing yeshiva but his wife will expect them to dress more modern, they will never be accepted. One of them will have to give in, and the consequence is that the shalom bayis ends up becoming severely compromised. Other than the way she dresses, I am hoping she is willing to live a Torah life.

My big question is why, if he is so observant about dress codes, did he date her in the first place? He surely must have known that she wears pants. I cannot imagine that she hid that from him. And the same can be said about covering her hair after marriage. I have a feeling that discussion, or at least some reference to it, came up earlier in the relationship, and he knew exactly where she stood on those issues. So why did he wait until she expects to hear a proposal from him to have all these misgivings? Could it be that he is getting cold feet as things are progressing? Is it possible that he is looking for a way to get out of the relationship, and the rabbi is smart and perceptive enough to recognize that?

Whatever is going on with this gentleman, I think that it is way over your head. Your focus should be that he does not do anything impulsive that he may later regret. Discuss with him what I have suggested, and please advise him to make an appointment, along with the young lady he is dating, to meet with a professional specializing in couple’s therapy.

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 Bsebrow@aol.com. Questions and comments for the Dating Forum can be submitted to 5townsforum@gmail.com.

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