Dear Penny: My Sister Is Broke Due to Her Freeloading Sons. Do I Help Her Anyway?

A mother and son look unhappy.
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Dear Penny,

My sister left her husband and moved into the city I live in now, living a block away from me. Shortly after, her two sons (currently 28 and 25) moved here also and live with her. 

The eldest hasn't worked since 2017 because my sister says he has anxiety issues. He's worked before, and it's my view he's manipulating her. He signed up for COVID unemployment in 2020 and received it until I brought attention to it. I've had anxiety and stutter my entire life and I've worked since I was 14. The youngest works off and on. He will work a job for a few weeks and then quit because it's not exactly what he wants. He has this luxury of course because he has a roof over his head and food.

My sister is a schoolteacher who will turn 61 in a few months. The burden of all the bills usually is on her. She also drives Uber and tutors to try to make ends meet. She received $40,000 from her divorce last year, and that money is already gone. Her sons won't get the COVID vaccine, and the younger one was in the hospital for two weeks. I'm pretty sure she paid the hospital bill with her divorce money.

I spoke to her last night and she is super down because her car broke down so she can't Uber to make money for bills. She can't afford to pay the rent and will have to pay the cost of the car being fixed in payments. 

I've spoken to her many times about how she should insist that her sons work to help out. She now just shuts down if I talk about it. I'm sure she won't change her situation. 

My question is, I could help but I feel it would be enabling the situation and she would be in the same situation in a month or two. I don't really have extra money but do fine. Should I help out financially when there are three possible breadwinners in the house and they aren't helping? I've offered to find her financial counseling as well.


Dear M.,

Your sister knows what you think about her sons. So since you’ve said your piece — plenty of times, it sounds like — you should consider helping only if you can accept your sister’s choices. That doesn’t mean you have to approve. It’s more of a why-beat-a-dead-horse type of thing.

But I do think helping your sister out makes sense. It sounds like the car repair bill could be the domino that causes everything else to collapse. If your sister can’t pay rent and gets evicted, she’ll have difficulty finding housing for years to come. If she falls behind on bills, she’ll destroy her credit. Bad credit is notoriously expensive, triggering exorbitant interest rates plus security deposits for just about everything.

It’s frustrating when you see how someone’s decisions compound their troubles. None of us gets life right every single time, though. And I think your sister sounds like she’s doing the best she can. She’s clearly a hard worker if she’s pursuing side hustles while also working as a teacher. Her sons may be making it harder for her to get ahead financially, but I think she’s also had some bad luck. Since it sounds like her divorce was recent, drawing hard lines with her children may be more than she can emotionally handle right now, even if they are a burden.

I don’t think you’re enabling your sister if you offer to help with the car repair bill. But you need to make this a gift, not a loan. If there’s one thing I’ve learned from writing this column, it’s that giving money to family members with the expectation of getting repaid is among the fastest ways to ruin a relationship.

It doesn’t sound like your sister has actually asked you for money. Regardless, if you help her out, make it clear that this is a one-time assist. Tell her you’re not in a position to make this a repeat occurrence. Should she ask you for money in the future, tell her no to avoid making this a pattern.

Normally, I’m not a fan of gifts that come with strings attached. But in this case, it might make sense to tell your sister you’ll help her on the condition that she accept your offer to help her find a financial counselor. Financial counselors tend to work with people who are struggling with the basics, like budgeting and debt. You can find one through the Association for Financial Counseling & Planning Education’s search tool at

There’s no guarantee that your sister will make any significant changes, of course. Sometimes we’re more willing to listen to advice when it comes from a neutral third party, though.

You clearly care about your sister. You’ll probably feel even more pressure to help her if this situation escalates further and she’s falling behind on bills because she doesn’t have a working vehicle. So if you’re inclined to help out your sister, don’t delay. Bailing her out now will be way less costly than if you wait until her finances have imploded.

Robin Hartill is a certified financial planner and a senior writer at The Penny Hoarder. Send your tricky money questions to [email protected].