At the Last Second
I took my first ever solo vacation when I was 24 to Ireland. When I got there, I was tired from the flight and confused by the car rental system (I had never rented a car before). I accidentally overpaid for the total coverage Cadillac insurance package. When I got to the place where I was staying, I called my dad about it.
He called the car company, figured things out, and told me that the next day I could drive back to the airport and get my money back for a less crazy insurance package. At the last second, I figured I’d never driven in another country, much less switching to the opposite side of the road, so I decided to just keep the insurance.
Halfway through the trip, I made a boneheaded mistake, hit another car, and totaled my rental car. I didn’t pay a penny.
Story credit: Reddit / Ohtarello