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

Some people don’t recognize a favor, and this Redditor got stuck paying for a whole Airbnb while waiting on one guy to “send the money later.” The trip was supposed to be simple, $56 each, split cleanly. Instead, it turned into an uncomfortable standoff that left the OP watching the calendar, watching the credit card bill, and watching the other person quietly disappear.

Here’s the cast: OP’s girlfriend paid through her credit card, OP’s girlfriend’s friends were in the mix, OP’s friend paid, and then there was one extra guy OP never even met before. He missed the payment, sent random texts about pranks, promised he’d pay on the 17th, then claimed he accidentally spent everything. Now it’s the 31st, OP still hasn’t seen a cent, and OP is trying not to cause drama while his girlfriend unknowingly has to deal with the credit card.

Now he’s wondering if he really is the problem.

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

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Original Post

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

This awkward standoff over $56 is just like the nail salon fight where someone debated tipping, after a $35 tip on a $105 mani pedi.

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

That’s when the “I’ll pay you later” guy starts texting OP from a number OP never gave him, like this is all just part of some prank schedule.

After the 17th rolls around and he says he spent the money, OP is stuck between letting it slide and watching his girlfriend’s credit card get hit.

The awkward part gets worse when OP asks for the $56 for the Airbnb and the guy keeps acting like it’s somehow tied to a future trip.

And by the time OP checks again on the 31st, the only thing that’s really “owed” is the silence, because OP’s friend and his friend are still not in the loop.

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.

Nobody wants to be the person chasing $56 while everyone else gets to pretend it’s not happening.

For another boundary blowup, see what happened when a 14-year-old refused to share her tipex.