By Baila Sebrow


I am dating a woman who is divorced. She is a very nice young lady, and her divorce was amicable. In terms of finances, her parents help her out a lot, and I understand that her ex-husband pays all the bills; she has everything she needs.

When we first started going out, I was taken aback that she doesn’t work. When I asked her about it, she told me that she doesn’t have to work. She does keep busy volunteering whenever she can. She is a very helpful person and is the first to offer to bake cookies or cook a meal for someone. But the fact that she doesn’t work scares me for the future. I know how these things go. Once we get married, her financial support will stop and I will have to become responsible for her and her four children. She is willing to sign a prenuptial agreement, but still, I want her to get a job. She says that she has not worked in many years and that she has no real skills. We do plan to have more children, and the costs are very high these days to raise a family. 

I earn a very nice salary, so it’s not like I need her to buy the groceries. However, my ex-wife did not work, and it made a difference in our lives and in the way she looked at things, though I am not saying that is why we got divorced.

The other thing is that she has been divorced for a long time, and she has lots of friends, both women and men. It’s not that she hangs out with men alone, just in a large group, but that does bother me. Am I overreacting here?


It sounds like you are coming from similar places in life but your personalities are clashing. While the issues you presented may not be a problem in a first-time-around marriage, remarriage after divorce is always challenging at best.

Remarriage after divorce requires ongoing compromises and negotiations on both sides. Both partners lived a particular type of lifestyle that clearly did not serve to the benefit of the marriage. Then, going through a divorce, dealing with the circumstances, and subsequently rebuilding one’s life can be very draining. In such cases, people do not want to walk into a situation that demands seeing it from the other person’s point of view. They typically want to walk into a home where the situation will be less cumbersome than what they previously experienced. That is why second-time marriages occur with less frequency and also the reason why the statistics for divorce go up for those who have been divorced.

You see problems now, and I am telling you that there will likely be more developments arising that will make you feel uncomfortable and second-guess your decision to marry her. I am not trying to scare you, but I am from the school of thought that people need to know as much as they can so that they make their choices with eyes wide open and clarity of mind.

What may have been considered normal and acceptable in the young lady’s marriage to her first husband is very different from the way you aspire to live your life with her. It sounds like her ex-husband did not want her to work, and he preferred that she be a stay-at-home wife and mother. And from the way you describe her, she sounds like a very giving person, not someone who sits around bored and bitter. I am saying this because although your ex-wife did not work, according to you, her lack of employment was somehow problematic in your marriage. The woman you are dating probably does not understand why you have an issue with her not working. Moreover, she has not been formally employed anywhere for a number of years. Realistically, that will not place her on the top of the list of applicants applying for whatever job will appeal to her. When it comes to hiring potential employees, recruiters and employers seek the most qualified person and one who has experience in that specific field. She might be able to get an entry-level position, but will she be happy accepting a minimum-wage salary, especially because she will feel that she was pressured to get that job? Not only that, but will she be resentful to get up every morning and go to work because she is not enjoying her job? Additionally, what is her level of education? If someone does not have a college degree, the chances are yet slimmer, even for that entry-level job. That might mean seeking job opportunities that may leave her feeling degraded or exploited, since she did not want to do that in the first place.

You need to look at it from her point of view. Since she has not worked in a long time, should she ever contemplate employment, she will not be the most desirable candidate applying. Not only that, but if she married young and did not have the opportunity to further her education, what type of job could she even get, and for what pay? Additionally, since you plan to have more children together, are you saying that you want her to work and take care of the children she has in addition to your growing family, iy’H?

I am wondering if your concern might be stemming from your fear that if she is used to a lavish type of lifestyle, once she is married not only will her present financial support cease, but you could be placed in the position of continuing to support her in the manner she is accustomed to living. Perhaps you’re worried that even though you earn a good salary, it may end up not being enough. I do see situations where the second husband cannot support his new wife in the way she wants, or, if he can, he may not want to live extravagantly. Plus, I am sure you want to protect your finances, and you have your own ideas about how to live life. I am happy to hear that you suggested a prenuptial agreement. In this way, you are both fully aware of each other’s expectations regarding money.

You brought up another issue. You are worried about the friendships she has with other single people. I don’t know the extent of her friendships. But she has been divorced for a long time, and rather than divorced people sitting around feeling lonely and distraught, hanging out in groups with men and women is typical nowadays depending on one’s hashkafic level. If she is going out to dinner with a bunch of people, or having Shabbos meals together, and is not alone with any particular man, then, frankly, it does not sound like she is doing anything wrong. Even talking by phone to a man whom she considers a friend may not necessarily be a matter of concern. If this young lady is a sociable person, having people in her life may be as necessary to her as food and water. You need to ask her very specific questions that are on your mind. But I caution you to be respectful of her and never to make her feel as though you are denigrating her or criticizing anything, even though you may not agree with her lifestyle.

The question is how she plans to live her life after she is married. Asking her to give up her friends just because you don’t approve will feel controlling and abusive to her. Don’t do it. If you are known to be a couple, suggest that she bring you around to be part of that group. Or if your relationship has not yet been made public, then tell her you expect to be included in her get-togethers after you are married. It is possible she may not have any interest in her single friends once she is married. But if she intends to continue her friendship, then you should expect no less than to be invited to be part of that group, too.

Whatever she tells you about her current friendships, I advise you to be open-minded and respectful of the fact that she has loyalty towards them, particularly if they were there for her when she was going through her own struggles after her divorce. Furthermore, she likely shares a certain amount of solidarity with them, as they went through similar challenges and were there for each other. Such bonds are strong. However, she needs to balance her relationship with you in a healthy way. If you want her to stop communicating with her male friends even by phone, you have every right to ask that of her if you are really serious about marrying her. She also needs to feel confident that you are serious about marrying her. If she thinks that you may drop her at any point, then I doubt she will want to take the chance and lose her friendships for nothing.

With the issues you are facing, I strongly believe that you will both benefit from couple’s therapy. My concern is that talking it out alone will cause one or both of you to feel defensive, and that can be detrimental to the relationship. A qualified therapist will guide you and help facilitate healthy communication so you will be able to air your concerns and also be heard. The feedback you will ultimately receive from those sessions will assist you in making a decision about proceeding with the relationship. Obviously, there needs to be a compatible relationship with the therapist as well. Meaning, you both need to feel that this professional is someone who could help you. Please understand, however, that even with therapy, the differences between you and the young lady may still be irreconcilable.

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 Baila also hosts The Definitive Rap podcast for and Israel News Talk Radio. Questions and comments for the Dating Forum can be submitted to Read more of Baila Sebrow’s articles at


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