29-year old who constantly borrows money from friend, including a $300 'emergency PS5,' without re-paying then bothers him for $60: 'You still owe me hundreds, and I've never hounded you about it

Author image for JR Atkinson
JR Atkinson • Writer and Editor
Jan 30, 2025 4:00 PM EST

Borrowing money from friends can be wildly uncomfortable. You want to keep it fun and friendly and polite, but at a certain point, you also might need your money back. If you sweep things under the rug and let them go by, you might end up resenting each other for unpaid debts or unbalanced books. This is why it's important to be up-front and honest in the moment. If you need someone to pay you back, you should hit them with a Venmo request and keep reminding them about it until it's paid. It might be slightly awkward to do, but it saves you a potentially ruined friendship down the line. 

This is way easier said than done, though. Money is an uncomfortable subject in this country, and everyone has different means. You also can't assume someone's financial status. Even if they seem like they're doing okay, you never know what's going on in their bank account. 

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  • 01
    'Never lend him money again' 1004
    via Donovan Grabowski

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

  • That's what happened in this situation when a pair of friends fell into an unhealthy pattern of borrowing/lending money and then not following up on it. That is until the tables were turned and suddenly payment was an urgent need. Read on for the details and see what you think. 

  • 02

    AITA for refusing to pay my friend $60 that I owe him?

    I, 30M, and my close friend 'Jake', 29M, have been close for years. Over the years, I've lent Jake money so many times. I'm talking $50 here for gas, $100 there during a trip, even once $300 when he needed to buy an 'emergency' PS5. I never really kept track because I trusted him. He paid me back some of it over time, but he still owes me a decent chunk, which I've never bugged him about. He would occasionally 'gift' me skins in the games we play in an attempt to balance the books.
    via u/bluenymous
  • 03
    A few weeks ago, Jake covered my $60 when I left my wallet at home during a group dinner. I told him I'd get him back, but life got busy, and I totally forgot. A few days ago, he texted me, "can you send me that $60 from dinner?" I apologized for forgetting and said I'd send it that night to which he replied, "I shouldn't have to chase you for this, man."
    via u/bluenymous
  • 04
    That rubbed me the wrong way. I didn't say anything in the moment, but it really started to bug me. I thought about all the times I've lent him money and how I never pressured him to pay me back. I've never once sent him a passive- aggressive text or made him feel bad about it.
    via u/bluenymous
  • 05
    So, I didn't send him the money right away and instead told him, "Look I get that I owe you $60, and I'll pay you back but let's not pretend this is some one-sided thing. You still owe me hundreds, and I've never hounded you about it."
    via u/bluenymous
  • 06
    Jake didn't take that well. He said it's not the same thing because I never asked for my money back, so it's on me if I didn't care enough to get it. So now he's ped at me thinking I did not pay him back intentionally and saying I'm deflecting to avoid paying him back, and that I'm being a stupid friend.
    via u/bluenymous
  • 07
    I feel like I'm in a weird spot here. Yeah I owe him $60, and ofcourse I'll pay it back. But on the other hand, his reaction feels so hypocritical given everything I've done for him financially over the years. AITA? Edit: I paid him back like I always intended to do.
    via u/bluenymous
  • 08

    Commenters weighed in on how he should approach this sticky situation.

    Giddy UpKitty • 2h ago Jake is a hypocrite, and also an unblushing user. Time to make him grow up, OP. Send a new text: "Heya Jake, this whole thing is leaving a bad taste in my mouth. We both know that
    via u/GiddyUpKitty
  • 09
    you owe me way more than $60. I haven't been hounding you for it, but that doesn't change the fact that you borrowed the money, you said you'd pay it back, and you owe me. It's been bugging me for quite a while. My best calculation of the total you owe me is $450.
    via u/GiddyUpKitty
  • 10
    "I talked to a couple folks and I'm going to take their advice here: I'm setting off my $60 debt against your $450, so now you owe me $390. And just so things don't get any weirder than they are right now, please understand that I can't lend you any more money until that $390 is paid off." NTA for putting an end to the blod, OP.
    via u/GiddyUpKitty
  • 11
    Cheezburger Image 10460779776
    via Alexander Grey
  • 12
    Puzzleheaded-Age... 2h ago NTA - I would be furious at his dig. Even before the dig I was on your side, but that pushed it way over the edge. Are you sure this is a friendship worth maintaining?
    via u/Puzzleheaded-Age-240
  • 13
    owls_and_cardinals • 2h ago I lean NTA. Your friend is being extremely hypocritical. "I shouldn't have to chase you for this, man" and then also "How was I to know you wanted it back when you never asked?" are in direct conflict with one another.
    via u/owls_and_cardinals
  • 14
    It shows you a LOT about his character in my opinion. It might be cleanest to pay him back and also FFS cut ties with him. Or you could do the math and explain that rather than paying him back, you're going to let that money
    via u/owls_and_cardinals
  • 15
    apply towards his debt and by the way, he should officially consider THIS the 'ask' (that you shouldn't have to do, according to him) so that he knows you do indeed expect to be paid back. Your friend's a flaming AH.
    via u/owls_and_cardinals
  • 16
    Savings_Telephone... . 2h ago Just say, I shouldn't have to ask you for the money you owe me because, as you told me, "I shouldn't have to chase you for this, man."
    via u/Savings_Telephone_96
  • 17
    Voidfishie • 2h ago NTA as soon as he said "I shouldn't have to chase you" and then followed up by saying "it's on you if you didn't care enough to get it". Totally hypocritical.
    via u/Voidfishie
  • 18
    Blitzkriek • 2h ago . I don't have a judgement, but I do have a solution. Pay him back the $60 and then never loan him money again. Consider it the cost of a lesson learned. Think of all the money you'll save by never having to give him. money again.
    via u/Blitzkriek
  • 19
    Loisalene • 2h ago NTA --- I've never heard of an emergency game system. Emergency car repair, emergency medical bill...emergency play time? Nah, you're nice to even consider paying this leech back.
    via u/Loisalene
  • 20
    196... • • 2h ago Edited 2h ago NTA. I think you were right to pay him back the $60. That way you keep the high moral ground here. Jake is clearly the kind of guy who has no problem borrowing money and not
    via u/1962Michael
  • 21
    repaying it, and putting it on you to "hound him" for the money. Even though he himself said that he "shouldn't have to hound" you. I will bet that he has a habit of asking for money and NOT calling it a loan, and not saying things like "I'll get you back." Leaving it ambiguous as to whether it's a gift or a loan.
    via u/1962Michael
  • 22
    I think it's OK for you to spell this all out to Jake, and ASK him if, in his mind, he owes you any money for anything in the past. And if he says no, then accept that. THEN you mutually agree on how you're going to handle this going forward.
    via u/1962Michael
  • 23
    One clear solution that doesn't need to be awkward is a Venmo request. As soon as you cover someone, you put in a Venmo request (within a day), and that's all the "hounding" you ever need to do. Let Venmo "keep score." And if it's a gift, then of course you DON'T put in the Venmo request. Then it's clear you don't expect to be repaid.
    via u/1962Michael
  • 24
    shanghai-blonde • 2h ago Pay it back and never lend him money again. Tbh I'd end the friendship over this but I'm quite petty haha it's the audacity that gets me, it's not about the money
    via u/shanghai-blonde
  • 25
    Sleepy_Doge97 · 2h ago NTA Life gets in the way, people forget things, you said sorry. He was out of line dropping that obnoxious "chasing" comment.
    via u/Sleepy_Doge97
  • 26
    • magicmom17 2h ago ESH. You had an agreement with him to pay him back. Honor that agreement. But yes. He should pay you back without needing you to remind him. Wonder if his strategy of "I don't owe someone money until they remind you" would work for if his credit card company didn't send him a statement? His excuse is a childish, selfish one.
    via u/magicmom17

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friendship aita AITAH best friends money problems friends listen to your friends reddit story family feud debt reddit thread Reddit lending money discourse borrowing money money
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