My Holiday Trip Fell Apart After I Refused To Pay For My Brother’s Dinner

It was a dream of my wife and I to visit Japan, so we planned a trip there with my brother’s family. My brother and I didn’t have the closest relationship, but we still get along well, so I thought, why not?

The planning phase went smoothly. My brother proposed that we rent a car there so we could drive across prefectures and explore. He also suggested that he will be the main driver since he and his family are familiar with Japan and he had an international driving licence.

Once we were there, we enjoyed every moment of it. Japan’s scenery was just as breathtaking as we imagined, and the entire group had fun. Everything went so well until something happened.

On the third night, the entire family was at a seafood restaurant in Ishikawa. My wife and I wanted to try king crabs, so we ordered one for ourselves. My brother’s family saw it and decided to order some too.

When the check arrived, my brother hinted that I should buy him and his family dinner. It wasn’t unusual for us to treat each other occasionally, but that dinner came up to over S$1,000! I paid for it and thought we could talk about splitting the bill later that night.

However, when I brought it up, he lashed out at me for being "cheap," and said that after driving us around for three days, the least I could do was pay for dinner. I tried to reason with him and pointed out that I had already contributed to the travel expenses, including petrol and car rental fees. But he was still furious and accused me of being ungrateful.

Then for the remaining days, my brother’s mood changed, and the trip turned sour.

From that experience, I made myself a promise: if I ever travel with family or friends again, I will make sure everyone is clear on their contribution of every meal and expense, no matter how inconvenient it might be. It’s the best way to preserve friendships and family relationships while travelling, so no one ends up feeling shortchanged.

This article is part of TSS Confessions, a weekly column where we delve into personal finance topics that are unscripted and genuine real accounts from people.