Woman forces friend with $300 to her name to give $40 to a homeless person after she already spent $50 on their coffee and food: 'Your friend was playing the big-hearted philanthropist with YOUR money.'

Author image for Emmy Pratt
Emmy Pratt • Senior Editor
Oct 30, 2026 8:00 AM EDT

Nobody should offer anyone money that isn't theirs. If you have money, you can do whatever you want with it, even if it isn't technically "wise." But anybody who takes money out of your pocket, says they're going to pay you back, and doesn't do that is a horrible friend. It doesn't matter how noble the cause was. 

Advertisement
  • 01
    Homeless sleeping on the sidewalk
    via Curated Lifestyle (Unsplash+)

    A homeless woman sleeping on the side of the street. 

    Representative only.

  • 02

    Am I wrong for not wanting to spend $40 on my first paycheck on a homeless person?

    I just got a new part time job after 6 months of unemployment. My first paycheck was less than $300. I was hanging out with one of my closest friends after our shift together, I paid for both of our coffee and food already (like $50 worth- but I
    via u/AffectionateVirus576
  • 03
    didn't mind because sometimes she'll pay for me for food and coffee too) after we ate we decided to go to the mall and we stumbled upon a woman who seemed homeless right outside an old navy. She was asking us to get her socks from there, I
    via u/AffectionateVirus576

    First of all, it is wild that someone who just got off a stint of unemployment is fully paying for $50 worth of food and coffee. If you make $150K and your friend makes $200K, then it's fine for one of you to cover the other's food. Heck, it's okay to do that if one of you makes $55K and one of you makes $70K! But nobody with $300 to their name should be buying anything but the absolute necessities until they have at least $1000 saved. The only exception is if you're a teenager or college student who is financially supported by your family. 

  • 04
    was about to say no when my friend offered her. My friend told her she didn't have her card but I could pay and she would Venmo me without really asking me if that's okay at first. I went along with it only because she promised to pay me
    via u/AffectionateVirus576
  • 05
    back for it, I had no intention on helping tbh. We go in and the strange lady suddenly went from a pair of socks to 2, to a shirt, asked for jeans, and at the register grabbed 2 snacks and I was the one who paid for it all. It totaled $40. My friend kept saying
    via u/AffectionateVirus576
  • 06
    she would Venmo me back which is the only reason I wasn't 100% saying no; despite being extremely uncomfortable and slightly upset. It's been a day now and my friend still hasn't paid me a dime back from it, and to be honest I'm getting
    via u/AffectionateVirus576
  • 07
    more and more upset about it the longer I go unpaid. I feel like an a hole for not wanting to use my own money to help out, I don't have much of it honestly. Should I ask for her to pay me back the $40 or just tell her since we were going on a
    via u/AffectionateVirus576
  • 08
    trip together to keep the $40 for gas since I was planning on covering for that. I've never had this happen to me and I just am shocked by the audacity to offer my money to a stranger and promise to pay me back but never do.
    via u/AffectionateVirus576

    This friend seems to have a pattern of not repaying her. Notice how, earlier in the post, she says her friend "sometimes" pays for her food and coffee, too. I have to imagine that her friend pays for her stuff far less frequently than she pays for her friend's stuff. I also imagine she pays for her friend's stuff because her friend regularly pressures her into it, not out of kindness. It's normal for high earners to pay for other people's food, and it's normal for significant others to do so, but not for friends who are individually struggling with money. You can even set aside part of your budget to help the homeless if that's where your generosity leads you. But if you only have $300 to your name, you're not in a position to give generously yet. 

  • 09
    edit: I sent her a message giving her my Venmo username and to send the money when she could. As for people calling me spineless or pushover, I don't care what she does with her own money, if she wanted to spent her last cent on a
    via u/AffectionateVirus576
  • 10
    potential scam, I only didn't say anything because she was promising to pay me back constantly while we were in there. Lesson learned from my end.
    via u/AffectionateVirus576
  • 11
    VisualStruggle891 NTA. Your friend was playing the big-hearted philanthropist with YOUR money. Send her a Venmo request right now and don't cover her gas until she pays you back.
    via u/VisualStruggle891
  • 12
    Affectionate Virus576 OP Thats a good idea, I wanted to avoid any awkward conversations but I might have to just send the request after that
    via u/AffectionateVirus576
  • 13
    Sufficient_Song3387 You can't avoid awkward conversations when someone owes you money. That's how you allow yourself to get taken advantage of.
    via u/Sufficient_Song3387
  • 14
    Katcar2007 In the future don't spend any money that is promised via Venmo from her unless she Venmo's you right then and there. She may have forgotten her card but I guarantee you she had her phone with her.
    via u/Katcar2007
  • 15
    hyundai-gt NTA but grow a spine. No is a full sentence. It is not your responsibility to solve other people's issues.
    via u/hyundai-gt

    This is sad, but true. Somebody who has been out of work with only $300 to their name is close to becoming homeless themselves. It's perfectly reasonable for somebody in that position not to want to give a big chunk of their paycheck to somebody else, even if they're objectively in more need than they are. As all pre-flight videos say, put on your own oxygen mask first before helping others. That said, some people have more money than they can spend in one lifetime and still think they don't have enough to give to the less fortunate. You should try to foster a spirit of generosity throughout your life, but not because somebody pressured you into it. 

  • 16
    Affectionate Virus576 OP I had no problem if she actually held her end of the promise by paying me back. I would've said no initially if I knew that wasn't going to happen. She probably told me 5 times in the store she was paying me back so I believed it. But yeah definitely gonna say no moving forward
    via u/AffectionateVirus576

    This makes her behavior so much more egregious. She should have paid her back as soon as she paid for the woman's stuff. 

  • 17
    Effective_Olive_8420 NTA. "Friend, I had been out of work for 6 months and just gotten my first paycheck for $300 when I gladly treated you to a meal! Then you offered to cloth someone, with the promise to pay me back because you did not have your card. I did not want to have anything to do with this, but trusted you at your word. You still have not paid me, and this puts me in the awkward position of having only $200 left after being unemployed for 6 months, and having to write to you about thi
    via u/Effective_Olive_8420
  • 18
    SlipInternational439 I grew up in a small town but ended up in the big city. I've heard all the stories. You were scammed. Your friend was scammed. You went along with it. This person may not have even been homeless. Even if they were, if they ask for "A" then start asking for "A plus B plus C", you aren't legally required to just say YES. So learn to say NO and grow a spine.
    via u/SlipInternational439
  • 19
    Beneficial-Guess2140 And they returned it for cash
    via u/Beneficial-Guess2140
  • 20
    relativeisrelative I've had homeless folks pull this stunt on me too. One time someone asked me to buy them a snack at CVS. Fine. Then they go and grab a $100 gift card. I just said no. Even when people are in need, no one likes to be taken advantage of.
    via u/relativeisrelative
  • 21
    rockology_adam NTA, and insist your friend pay you back. One thing that is difficult to accept especially with your first job is that having an amount of money in your pocket is not the same as having impulsive freedom to do whatever with your money. If your friend says anything about not wanting to pay you back because you should be charitable... start limiting your time with this friend and never pay for anything for her ever again until she apologizes and pays up. If she's happy to give away
    via u/rockology_adam

    I know this is only one instance, but I really don't think that this person is worth keeping as a friend. If she pays her back, maybe she should get another chance, but her behavior doesn't show that she really cares about her friend.

    One more thing: it is 2026! This friend should have Apple Pay on her phone by now! 

Want More? Follow Us and Add Us as a Preferred Source on Google.

Tags

friendship charity poor money problems homeless friends unemployment money unemployed
Scroll Down For The Next Article