We need to talk about the most dangerous part of any friendship. It’s not politics. It’s not religion. It’s the group dinner bill at the end of a long day of drinking in the sun.
You know the scene. The waiter drops the check. Everyone freezes.
Then, the “Dance of the Wallets” begins.
Someone (usually the Responsible One) sighs and pulls out a credit card. "I'll just put it on my card to get the points," they say, bravely. "Everyone just Venmo me."
A chorus of "You're the best!" and "Sent!" erupts around the table.
But here is the dark truth: Half of those people are lying.
They haven’t sent it. They think they’ll send it later. But then you’ll go to a bar, and then a club, and then get late-night pizza. By the next morning, that dinner bill is a distant memory, buried under a hangover and three other Uber charges.
The "I'll Get the Next Round" Fallacy
The biggest lie we tell ourselves on group trips is, "I’ll get this round, you get the next one. It’ll all even out."
Spoiler Alert: It never evens out.
Unless you are traveling with a group of mathematicians, "evening out" is a myth.
- Person A buys a round of craft cocktails at a rooftop bar ($85).
- Person B buys a round of beers at a dive bar ($24).
- Person C buys everyone gelato ($15).
In their heads, they all "bought a round." In reality, Person A just financed the evening, and Person C got away with murder.
The Post-Trip "Request of Shame"
This leads to the worst part of the trip: The week after you get home.
You’re sitting on your couch, staring at your credit card statement. You realize you spent $400 more than you thought. You start scrolling through receipts. You realize that Mike never actually paid you for that boat rental.
Now you have to do the unthinkable. You have to send The Text.
"Hey! So fun last weekend! 🌴 Just doing some admin, looks like the boat was $50 per person? No rush!!"
You add the "No rush!!" and the exclamation points to soften the blow, so you don't sound like a loan shark breaking kneecaps. But you feel gross. You feel like a nag. And Mike feels annoyed because the trip is over and he’s back to paying rent.
Stop Doing "Napkin Math"
The problem isn't your friends (usually). The problem is that we are trying to do accounting in our heads while on vacation.
Vacation Brain is not capable of complex division. Vacation Brain wants another margarita.
If you rely on memory or crumpled receipts, someone is going to get shortchanged, and someone else is going to accidentally free-load. Resentment builds silently. And nothing kills the vibe of a trip faster than feeling like you’re the only one paying for it.
Let the App Be the Bad Guy
This is exactly why I built the Expenses feature in PlanAwesome. I wanted to stop being the "Bill Collector" of my friend group.
I wanted a robot to do the dirty work.
Here is how it changes the game:
- Log it immediately: You pay for dinner? Open the app, type "$150," select who was there, and hit save. Done. You can forget about it.
- Split it fairly: Did Sarah not drink? Uncheck her name. Did Dave order the wagyu steak? Assign him a higher specific amount.
- The Running Total: The app tells you who owes who in real-time. You don't need to swap money 50 times a day. You just pay the net difference at the end.
Save Your Friendships
Money is awkward. It just is. But pretending it doesn't exist usually makes it worse.
The best way to be a chill traveler isn't to be loose with your wallet—it’s to be organized so nobody has to worry about it.
So next time the check comes, don't do the "I'll get you later" dance. Put it in PlanAwesome, put your phone away, and order another round.
(But seriously Mike, if you're reading this, you still owe me for the boat.)