41-year-old brother borrows $16K from 39-year-old sister over the years, insists that she give him more money after she gave him $2K just 2 weeks before: 'My husband and I just had a 3 hour conversation with him saying no!'

Author image for Emmy Pratt
Emmy Pratt • Writer and Editor
Jun 7, 2025 8:00 PM EDT

You really can't help someone who refuses to help themself. You can throw as much money as you want at a situation, but it will not address the underlying issues of irresponsibility and dysfunction that lead to the need for extra money in the first place. It's difficult to accept that you can't do anything to fix someone else's problems. It's really painful to watch someone you love ruin their life, and not be able to do anything about it. But if you've already tried to help and they keep finding themself in the same bad situation, you need to know when to step back and let them fail. You can't be your adult siblings' or adult children's keeper, and it helps nobody to keep enabling bad habits that hurt everyone involved. Sometimes a bootstraps mentality can be toxic, but not when you're drowning because of a history of poor life choices. 

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  • 01

    Older brother feels that I need to give him more money.

    I'm 39 and my brother, Todd (not real name) is 41. When I was 20, Todd damaged his car and wanted me to give him 2k. So I did. When u turned 22 I wanted my money back. He said it was God's money. Yes, that's what he actually said.
    via u/TrickyAd9597

  • The brother in this story does not appreciate the generous help his sister and her husband have given him over the years. He constantly takes advantage of them, and after years of this, the sister has finally decided that enough was enough. The brother didn't take the resignation of his cash-cow very well. 

  • 02
    Cheezburger Image 10514494208
    via David Cain

    The image does not depict the actual subjects of the story. Subjects are models.

  • 03
    When I was 29 he came to live with me and my husband and our 2 kids, 2 and newborn. My parents gave him 2k. He broke his car so we gave him our 99 camry we had bought used a year ago for 3800$. After 3 months of
    via u/TrickyAd9597
  • 04
    Cheezburger Image 10514502400
    via Jigar Patel

    The image does not depict the actual subjects of the story. Subjects are models.

  • 05
    living with us and not helping do any chores but continue to demand more money and food, I basically had to have him removed from my life. He became homeless for 3 years.
    via u/TrickyAd9597
  • 06
    At 39, he says he maxed all his cc and he is 2 months behind on his rent and needs money. I give him 2000$ and then like 2 weeks later he wants more money. My husband and I just had a 3 hour conversation with him saying no!
    via u/TrickyAd9597
  • 07
    Cheezburger Image 10514503936
    via Getty Images (Unsplash+)

    The image does not depict the actual subjects of the story. Subjects are models.

  • 08
    We will not. We don't owe you! Besides, he only calls when he needs money. He says he will be living on the streets unless we give him money.
    via u/TrickyAd9597
  • 09
    sydmanly Yeah, no
    via u/sydmanly
  • 10
    Big_Bookkeeper1678 It's time brother hits rock bottom. Your priority is your children. Looks like he owes you at least 16K (3 months rent/food 6K) and has done absolutely nothing for you in return for keeping him off the streets.
    via u/Big_Bookkeeper1678
  • 11
    TrickyAd9597 OP We actually do not need him to repay us back. We were really financially responsible and saved for the last couple of years and have decent savings.
    via u/TrickyAd9597
  • 12
    Complete Tell6795 But just bec you really don't "miss" the $$$, that doesn't mean that it's ok to just toss $$$ at him every time he comes around. You guys should have cut him off a long time ago. He's never going to get his sh together if you keep enabling him to live like this. Low on $$$, "Oh I guess I just hit up family for a couple grand like I always do ". This time, stick with the NO.
    via u/CompleteTell6795
  • 13
    Civic4982 "No." Is a complete sentence -- fits so well here but I already wrote that today. Sounds like he has a spending problem. Hopefully 41 year old Todd doesn't have other humans who depend on him.
    via u/Civic4982
  • 14
    Tricky Ad9597 OP No, single, no kids. No job.
    via u/TrickyAd9597
  • 15
    harrywwc add "no brains"
    via u/harrywwc
  • 16
    Vandreeson His problems are not your problems unless you allow them to be. He's done all this to himself.
    via u/Vandreeson
  • 17
    Korean Trouble Sorry to say, but you've been encouraging this behavior all his life. He's now a grown adult and needs to learn to be responsible... don't see that happening.
    via u/KoreanTrouble
  • 18
    Helpful_Hour1984 Seriously. After the "god's money" incident, Todd should've been weaned off OP's support.
    via u/Helpful_Hour1984
  • 19
    Mmmk63792 Wow yall were beyond generous. After that first 2k, I'd be side eyeing him if he asks for anything else! Y'all cannot enable him any further. He's an adult. He has abused your generosity and refused to be responsible.
    via u/Mmmk63792
  • 20
    Rugged Hangnail Every dollar you give Todd, you are taking away from your children, your husband and yourself. Every bit of time and energy you spend thinking about Todd, and getting angry about Todd, is time you are stealing from your children, your husband and yourself.
    via u/RuggedHangnail
  • 21
    Professional-End9600 This is the best response, and why a family whose actions lead to homelessness after attempts to help them is no longer your problem. Help people who are worthy of help and don't let any family member guilt you because you are related.
    via u/Professional-End9600
  • 22
    Mesa Adelante This sounds like my little brother. He always needs just $10 for the bus or trolley. Then he needs $10 more, etc. he was furious last night that I wouldn't send him $100.
    via u/MesaAdelante
  • 23
    IllustratorWeird 5008 My brother is the same. He needs to figure out a sustainable solutions for his needs instead of expecting people who financially support themselves, to also financially support him. In my case, I also have his ex constantly asking me for free money to feel and clothe the niece because my brother does not pay child support and the ex is bad with money and life choices. I know it's hard to say no because of the potential suffering, but they need to figure their shout. Not you
    via u/IllustratorWeird5008
  • 24
    Over the past 20 years, if he got 5 other donors to give the same amount, he basically doesn't have to contribute to society at all. It'll be hard to unlearn that lesson for him. It is NOT your problem.
    via u/IllustratorWeird5008
  • 25
    BrewDogDrinker No no no no. He has to be rock bottom.
    via u/BrewDogDrinker

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housing broke brother house car siblings money problems homeless wife cars no money husband rent sibling sister money big brother little sister
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