UPFRONT DEPOSITS

The trip was supposed to be simple: six friends, one annual getaway, and the same person doing all the booking. But after last year, the group's usual organizer stopped fronting the money.

Last year, the poster had put together the trip the way they always did, finding the Airbnb, handling the arrangements, and covering the deposit out of pocket. The cost came to $600. Everyone told them the same thing: "pay me later."

That later never fully came.

Only half the friend group actually paid the poster back.

So when this year's trip started coming together, the organizer changed one detail: they asked everyone to send their deposit first, before anything got booked. No more covering the upfront cost alone. No more hoping people would settle up after the fact.

That request did not land well.

Some friends pushed back, saying it was "making things complicated." Others accused the poster of "overthinking" the whole thing, as if asking for money before booking a shared trip was turning a simple plan into a hassle. One friend cut right to the point with a line that clearly stung: "you're usually good at this, what's changed."

But what changed was last year's unpaid bill.

The poster had already learned what happens when a group promises repayment without putting money down first. Six friends talked about the trip. Six friends benefited from the planning. Yet when the time came to reimburse the person who had covered the Airbnb deposit, only three actually did.

Now the poster wants to know whether asking for deposits upfront makes them the asshole.

It's a small group, a familiar tradition, and a very ordinary kind of money dispute, the sort that can slip into a friendship quietly and then sit there, awkward and unresolved, until the next trip rolls around and someone has to be the one to say: not this time.