By Esther Mann

Dear Esther,

My sister-in-law Baila is married to my brother Hesh. I like them both a lot. Sadly, Hesh has never been a success professionally. He’s a really nice guy and generally a good husband, but he’s never been able to provide for his family successfully. I’m not sure why he hasn’t been able to find himself in that way, but it’s very sad.

My husband, thank G-d, has always been able to provide for his family well. We’re far from rich, but he does more than OK, and I also work. I love working, and I do it more for the fulfillment I get from it than for the salary.

Baila and I have always been very close. For years now, Baila has been coming to me to “borrow” money. We both know, in the moment, that I will never see that money again. Not even a dime of it. But it’s the term she likes to use, and I guess I want to help preserve her dignity so I go along with the language. She’s never asked me for large sums of money, but they add up. She might ask me before the school year to loan her money to help her buy school clothing for the kids. (They have five children and, honestly, I don’t understand why they have so many children if they can’t afford to take care of them totally, but that’s something I will never ask about.) Before a yom tov, Baila might ask to borrow some money to buy a new outfit or towards buying some other stuff she needs. She once asked for help when her refrigerator broke and when she needed to replace a broken oven. The sums of money involved are never in the thousands. It’s usually a few hundred, give or take. But if I had actually kept a list of all the money she “borrowed” from me over the years, I’m sure it would amount to quite a few thousand dollars.

When Baila’s children were young, I understood why she couldn’t work. I realized that, without a degree, anything she earned would probably be less than what she would have to pay a babysitter. At this point, though, her youngest is five, and, as far as I can see, there is no reason why Baila shouldn’t be earning a living. I have often mentioned to her that she should go back to school and get a degree so that she can have serious earning power and be independent. I even come up with suggestions about things she’d be good at. Generally, the conversation goes nowhere. She has recently taken part-time jobs here and there that pay her next to nothing. Certainly not enough to keep her from coming to me to ask for a “loan.”

My husband and I always say that we are grateful to be on the giving end rather than on the receiving end. We are grateful to have been able to help out Baila, and, in that way, also help out my brother and their children. So when we are feeling particularly good-natured and noble, we just kind of pull out the checkbook. But I’m finding lately that I’m becoming resentful. Though Baila always thanks me/us profusely, I have made it so easy for her to ask for money that I doubt she thinks twice before asking. It’s become second nature to her. I have to wonder whether we are enabling her to stay dependent on us for the extras, and maybe if she didn’t feel she could always come running to us, she would be more motivated to take initiative and make something of herself.

One other strange piece of this puzzle is that for whatever reason, from the start, Baila has asked me not to say anything to Hesh. At the beginning, she would say that she didn’t want to embarrass him, and if he knew that she was “borrowing” money from me, he would be mortified and hurt. So as far as I know, Hesh knows nothing about our generosity over the years. Lately, that’s been starting to bother me as well. I feel that maybe I should let him know, and maybe if he knew, he would try harder as well.

So that’s where I’m at right now. I’m not sure whether I should say something to Hesh. I’m not sure whether I should finally tell Baila it’s time for her to grow up and take responsibility for herself more fully, or whether I should just close up shop and stop giving to her. The amazing thing is that through all of this, we have remained good friends, and I really do value our friendship, which I don’t want to ruin. But I am getting really frustrated. What do you think?

The Giver

Dear Giver,

First off, kudos to you for being such a generous, supportive sister-in-law and friend. Over the years, I’m sure you made all the difference in the world as you helped Baila pull it together in all sorts of ways and for all sorts of occasions. You and your husband made an enormous difference in her life and that of her family. That’s something you and your husband should always feel really proud about.

I’m curious to know what has been going on lately that finds you suddenly questioning your choices to be so generous and helpful. I don’t get the feeling from your letter that it has anything to do with your own financial situation changing. Is it strictly that whereas you once saw Baila as a victim of sorts, married to a man who couldn’t support her in the way that your husband was able to support you, your perception of her has changed because she now has the opportunity to make something of herself and she isn’t bothering to do so? Is it that you are suddenly starting to feel taken advantage of? It’s important for you to try and dig a bit and figure out why your feelings have changed. Understanding your new underlying dissatisfaction will help you determine where to go from here.

Regardless of what you discover about your own feelings, it’s important to realize that there may be more to this story as it pertains to Baila, Hesh, and their relationship. We could both speculate and come up with all sorts of reasons why Baila feels the need to turn to you consistently for monetary help. Maybe we would hit on something real and maybe not. But I do think it’s more complicated than it appears on the surface. People often do inappropriate things at times for reasons they are not even in touch with.

My point is, as you mentioned in your letter so beautifully, if possible, perhaps you should consider what it would look like to remain on the giving end of things. There is nothing you can do to make Hesh more successful. That’s something he will either figure out someday — or not. Why Baila asks for your help and why she isn’t more industrious is also something you probably won’t ever fully understand. It’s great to give her career advice, but if something is holding her back, I’m sure it goes much deeper than you realize.

So my advice is to get in touch with your sudden discontent, work through its source, and try to put it to bed. So long as helping Baila isn’t creating even the slightest bit of hardship in your finances, and assuming Baila doesn’t suddenly start upping the ante, maybe it makes the most sense to follow the old saying that “charity begins at home.” True, it’s not actual charity, but you’ve managed to meaningfully plug some sort of hole for Baila all these years. Why quit now?


Esther Mann, LCSW, is a psychotherapist in Hewlett. Esther works with individuals, couples, and families. Esther is presently offering phone, Zoom, and FaceTime sessions. She can be reached at or 516-314-2295. 


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