'He owes me thousands': Man in debt to best friend finally wins a bet, ruins friendship by relentlessly nagging for the payout

Author image for Isabella Penn
Isabella Penn
Aug 24, 2024 9:00 AM EDT

When you make a quick bet with your friends, do you stick to the payout? Say you bet your friend to do something silly in public, or maybe you bet on the outcome of a sporting game. If the other person loses, do you hold them accountable for paying you? It can go either way, but you have to be on the same page as the other person. One time, my friends bet someone in the group to go up and talk to their crush, and if they didn't, they would be removed from the group chat promptly for one week. Let's just say we didn't hear from her for a week. 

But if you're a friend who constantly loses bets and never coughs up the money, yet expects other people to when you win, then you're likely going to lose your friends pretty quickly, just like this guy did. This entitled man was constantly losing trivia bets with his friends. One friend claimed that "he thinks he's really smart, but he's not." See what happened next. 

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  • 01
    • r/mildlyinfuriating ⚫ 14 hr. ago FOOOOr Annoying friend finally wins a bet, won't stop pestering me for money.
    via u/F0000r
  • 02
    I have a friend, he thinks he's really smart...but he's not. Its to the point were he's constantly making bets for $100 on random trivia. Dumb things like ostriches have been known to swim across oceans to migrate since they can't fly,l. Foxes are
    via u/F0000r
  • 03
    the most beautiful type of wild cat. Tesla made every car in the world electric and the old ones take gas to charge their batteries. Jackie Chan was going to be a dentist but a scouting agent discovered him during an appointment. Just a
    via u/F0000r
  • 04
    constant parade of things most people know are wrong. He'll then get sheepish and kind of sweep the fact that he lost $100 under the rug. He never gave me any money for the any of the bets he lost. Its to the
    via u/F0000r
  • 05
    point were he owes me thousands if not tens of thousands. I never thought he was really serious about the money, it was just a quirk he had. So I never tried to collect or pressure him, I just let it go.
    via u/F0000r
  • 06
    Well it finally happened, I lost a bet over a bus route and he won't shut up about it. Constantly asking if I have the money, when is he gonna get the money, maybe he should start charging interest on the money ect. I told him I'd just take it off of
    via u/F0000r
  • 07
    the money he owes me. Well surprise surprise, he doesn't think he owes me any money. All those other bets in the 5 years I've known him were just joke bets.
    via u/F0000r
  • 08
    The only bet he won, well that was a real bet. This is the kind of kindergarten etiquette I do not expect from a man in his 30's. I don't think I want him in my life anymore.
    via u/F0000r
  • 09
    JimBob-Joe • 1d ago The way you described him makes him sound like hes 12. But in his 30s? The whole unit is defective.
    via u/JimBob-Joe
  • 10
    hmmmrmm 1d ago 05 I'm gonna pay you $100 to off.
    via u/hmmmrmm
  • 11
    SnooApples5554 • 1d ago "You don't have to pretend the bet was real this time. If you're that hard up for money, just ask." Just find a way to make it uncomfortable for him to keep harping. Ask to.see the contract. People playing dumb games aren't usually receptive to emotional maturity or growth, so I'd beat him at his own game lol
    via u/SnooApples5554
  • 12
    . Byakurane 1d ago You have 3 choices. 1. You tell him to cut the or you cut him off. 2. You say the previous bets werent a joke to you and he either pays you or back to 1. 3. You say the bet was a joke just like he always did and if he says no back to 1.
    via u/Byakurane
  • 13
    SingleHitBox ⚫1d ago Just tell him "It was a joke bet" get over it and move on with life.
    via u/SingleHitBox
  • 14
    HealerOnly . 1d ago "mildly infuriating" idk, friends like this is not worth keeping. I would just cut ties with him completely if possilbe.
    via u/HealerOnly
  • 15
    victraMcKee • 1d ago Ok read the signs. Your "friendship" has run it's course. Ghost him and be done
    via u/victraMcKee
  • 16
    AdventurousCelery89 • 1d ago It's time to cut ties if he only takes it seriously now that you owe him money, but it's just a game when he loses constantly, I'd tell him to get stuffed and kick rocks if he doesn't drop it
    via u/AdventurousCelery89
  • 17
    Vivid Possible6614 If 1d ago you never seen him again, that would be the best $100 you ever spent.
    via u/Vivid Possible6614
  • 18
    YomiKuzuki • 22h ago "Why are you saying I owe you money? It was just a joke bet like yours were. Unless those were serious bets. In which case this bet will be serious too. And you'll owe me interest on those. So either off with telling me you want that money, or get out of my life." And then kick him out of your life anyway.
    via u/YomiKuzuki
  • 19
    Humble-Vermicelli503 • 1d ago Have you considered going double or nothing?
    via u/Humble-Vermicelli503
  • 20
    B ComicsEtAl • 1d ago Just tell him you stopped taking his bets seriously the last several times he didn't pay up and you no longer take his bets seriously.
    via u/ComicsEtAl
  • 21
    Inevitable_Spell5775 • 1d ago What a strange individual.
    via u/Inevitable_Spell5775
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    Cheezburger Image 10392257536
    via August de Richelieu

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friendship bet drama friends relationships petty entitled reddit thread Reddit betting money
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