Money is one of the trickiest subjects to navigate between friends. It can turn the strongest bonds into a minefield of resentment and awkwardness, especially when one friend seems to have a recurring case of wallet amnesia. We’ve all known that person—the one who is always enthusiastic to go out, but whose memory conveniently fails them the exact moment the check hits the table. One reader, after months of unwillingly bankrolling his friend’s social life, decided it was time to stop being a friend and start being a bookkeeper.
My best friend Jake suffers from a very specific and convenient medical condition: Chronic Wallet Forgetfulness. It only flares up when a bill is due. For months, I’ve been his safety net, covering his share with a sigh and an empty promise of “I’ll get you back, man.” But after he stuck me with the bill for my own birthday dinner, I decided it was time to issue him a statement for his services. Literally.
The ‘Oh, Man, Not Again!’ Routine
Jake is a great guy, but he’s a financial black hole. The routine is always the same. We’ll go out, have a great time, and when the bill arrives, he performs the holy trinity of the mooch: the frantic pocket pat-down, the look of dawning horror, and the inevitable, “Oh, man, you are not going to believe this… I must’ve left my wallet at home.”
I, being the responsible friend with a steady income and a functioning memory, would always end up covering him. He’d promise to Venmo me later, or that he’d “get the next one,” but the repayment rarely came.
The final straw was my birthday. He insisted on taking me out to a nice steakhouse as his “special treat.” We went all out—nice steaks, a good bottle of wine. It was a great night, right up until the $200 bill arrived. Like a terrible magician performing his only trick, Jake did the pocket pat-down. “Dude, I am so, so sorry,” he said, putting on an Oscar-worthy performance of self-loathing. “I can’t believe I did this to you on your birthday.” I ended up paying for my own birthday dinner. That was the moment I knew something had to change.
The Ledger of Lies
I went home that night fuming. I knew arguing with him was pointless. I needed cold, hard, undeniable data. I sat down with my laptop and went through six months of my credit card statements. I created a spreadsheet.
I listed every single time Jake’s “amnesia” had struck and I had to pay. Every concert beer, every late-night pizza, every movie ticket. I listed the date, the place, and the exact amount. The list was shockingly long. The final line item was the steak dinner: August 28th – My Birthday “Treat” – $212.78.
I then turned the spreadsheet into a clean, professional-looking invoice. I titled it “INVOICE: For Services Rendered” and added a memo line: “Re: Chronic Wallet-Related Memory Loss.” The grand total was $487.32.
Payment is Now Due
A few days later, Jake texted, “Pizza tonight? My treat, for real this time!” I agreed. We met at our usual spot. Before the waitress could even bring us menus, I slid a crisp, white envelope across the table. “I have something for you,” I said, my voice completely neutral.
He opened it, a confused look on his face. His expression shifted as he read the title. I watched his eyes scan down the long, itemized list of his debts. I saw the exact moment he got to the entry for the steak dinner. All the color drained from his face.
He tried to laugh it off. “Bro, is this a joke? This is hilarious.” I didn’t smile. “It’s not a joke, Jake. That’s what you owe me. I love hanging out with you, but I’m done being your credit card. So, you can pay me back, or you can buy my half of the pizza for the next… 30 or so times we come here. Your call.”
The rest of the dinner was the most awkward silence of my life. But the next morning, I got a Venmo notification for the full $487.32. The memo just said, “Sorry.”
Our friendship is definitely on thin ice, but for the first time in years, our finances are settled. My other friends think it was a genius move. My sister thinks I was passive-aggressive and that I valued the money more than the friendship. I think I finally forced him to be accountable. AITA for sending my friend an itemized bill for his mooching?
This story is a perfect illustration of what happens when financial resentment is left to fester in a friendship. The narrator, pushed to his limit, chose not to have another pointless argument, but to present his friend with an undeniable, documented history of his behavior. The invoice wasn’t just a request for money; it was a physical representation of the one-sided nature of their friendship. It was a cold, hard, and arguably necessary, reality check.
What do you think, readers? Was the invoice a brilliant and justified way to handle a chronic mooch, or did the narrator nuke a friendship over a few hundred dollars? Let us know your thoughts!
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