Summary:
A friend known for absurd $100 wagers actually won one and now relentlessly demands repayment despite previous joke bets. I’m rethinking our friendship.
hey, i feel u. been there, bet da bet was jst a joke right? maybe have a chill talk bout boundaries, tell him its fun when its a joke, not when its real cash. sometimes friends forget the line, ya kno?
Man, I feel you on this one. I mean, when a joke turns into a never-ending money request, it can really mess with the vibe of a friendship. Maybe it’s time to have a heart-to-heart. Tell him how his constant cash demands are making you uncomfortable and that you miss the fun, easy-breezy days when wagers were just for laughs. I know it might be a bit awkward at first, but clearing the air could save a friendship and even add some extra respect for each other’s boundaries. Hang in there, and I hope you both can get your groove back! 
i once faced a similar snafus with a friend over what started as a joke bet. upon noticing his continuous tickling over cash, i decided to have a direct conversation, explaining that the wager was intended to be a one-time thing. the discussion was quite uncomfortable at first but ultimately proved necessary, as boundaries had to be established. this honest approach helped in clarifying expectations and saved the friendship from further strain. i suggest addressing the issue head-on, ensuring that both sides understand the original context of the bet.
hey, i feel u. maybe time to tell him the wager was a one-off joke, not a cash grab. if he won’t get it and keeps pressuring, u might need to set firmer boundaries or rethink where u stand in this friendship.
Hey there, I can totally understand how this could start feeling really off. It’s hard when a bet that used to be all fun turns into a stressful situation. I ended up in a similar mess when a friend took things too far. I sat down with him, explained that the wager was all in good fun and not something to pressure me about repeatedly, and it helped clear the air. It might also be good to reinforce that boundaries are important, and if he can’t get that, maybe it’s time to take a step back. I hope you find a balance that makes you feel respected and keeps things friendly! 