How A Simple Airbnb Split Became The Most Awkward Group Trip Ever: One Redditor's Uncomfortable Standoff Over $56

A Redditor recently found himself in an uncomfortable financial standoff after a weekend trip with his girlfriend, two of her friends, his own friend, and a newcomer he’d never met before. The Airbnb cost just $56 per person and was booked on the girlfriend’s credit card, leaving the OP responsible for collecting everyone’s share.

After the trip, the OP reached out in an Instagram group chat to request repayment, and while his friend handled it immediately, the other guy stayed mysteriously silent. The Redditor chose not to push, hoping the delay was just an oversight.

Things took a strange turn when the newcomer contacted the OP directly using a phone number the OP never gave him, kicking off the conversation with a prank about the OP’s workplace. The two ended up chatting casually throughout the day, and at one point, the newcomer even suggested another hiking trip together.

Sensing a good moment, the Redditor asked him to send over the $56 he owed, only for the guy to question why. The OP clarified it was for the Airbnb from the last trip, not some hypothetical future getaway.

The newcomer promised to pay on the 17th, so the OP and his girlfriend waited patiently, not wanting to seem pushy. But when the Redditor checked in a few days after payday, the guy admitted he had “accidentally” spent all his money.

With the credit card bill looming, the OP explained the urgency, only to be hit with the baffling question: “You can’t pay it off yourself?” The Redditor tried to remain calm, offered more time, and avoided telling his friend about the issue due to a recent tragedy in their circle.

Now it’s the 31st, the OP still hasn’t seen a cent, and the whole situation feels increasingly awkward. The Redditor is left wondering whether asking—again—for a simple $56 makes him the villain of the story or just someone trying to do the responsible thing.

The OP still hasn’t seen a cent, and the whole situation feels increasingly awkward.

AI-generated image

Here's the original post by Reddit user 'ITeeVee'.

I (M21) went on a trip with my gf (F22) 2 of her friends (F20s) my friend (M22) and a friend (M21) he brought (whom I never met before). The Airbnb was $56 per person and was paid through my gf's credit card. Few days pass and I ask in an Instagram gc with my friend and his friend to send the money for the trip. My friend pays shortly after, but I get nothing from the other guy. I don't want to rush him, so I wait cause of the benefit of doubt. He texts me randomly through his phone number (which I didn't give) to make some prank related to my work. I figured out it was him immediately and we just talked here and there throughout the day. He said that we should do another hiking trip with our friend, later on I ask for him to send the $56 to me. He asks "why?" and I tell him for the Airbnb. He thinks I am talking about the Airbnb for the "next" trip , then I tell him otherwise. He says he will get paid on the 17th and he will send it then, I say "okay" and let him be and my girlfriend also does not want to rush him. Few days after the 17th I check up on him and he says he "accidentally" spent all the money he got paid. This is to the point where my girlfriend needs to pay off her credit card already. He asks for an extension and I say "okay, just do it as soon as u can cause the credit card gotta be paid off", and he just says "you can't pay it off yourself?". Now as it is the 31st, I still have gotten nothing. My girlfriend does not know about the last message he sent to me, and I have not told my friend his friend owes me money as we are in the midst of a good friend's death. I honestly don't know what to do, and don't want to cause problems. I guess the question is, as I being an asshole for hounding the guy to send $56?

Here's how the Reddit community reacted.

ProfessorDistinct835

At least it was only $56.

pottersquash

"Oh, hell no!"

yuffie2012

NTA.

Dangerous_Data6749

"You will never see this money again."

voiceofgromit

A $56 life lesson.

Good_day_S0nsh1ne

Your girlfriend should probably be doing the hounding.

Parasamgate

Take them to court if you have to!

fast4help

Send him solo camping.

Ok-Nature-5440

He needs to pay in advance next time.

SuperLoris

"He doesn't intend to pay."

ScaryButterscotch474

"It doesn't sound like he can afford to go anyway."

iloceyourclock

"Ghost him."

Both-Buffalo9490

"Never loan to strangers."

JeanSchlemaan

In the end, the OP wasn’t asking for anything outrageous — just the money he fronted. Whether the guy pays or keeps dodging, the Redditor’s learned that even small debts can reveal big red flags.

And if there’s a silver lining, it’s this: the next trip guest list just got a whole lot shorter.