Why would you want your kid to buy pointless gifts before they pay off their debt?

There’s nothing worse than being the friend who pays for a concert, trip, or excursion, only to have to chase everyone else down begging for them to pay you back. I never buy the idea that someone merely forgot to pay someone back for something as big as a plane ticket or a hotel room. I’ve forgotten to pay someone back for a drink or an Uber, but never something that costs hundreds of dollars. The second the person who paid tells me how much the purchase cost them, the money is zooming out of my checking account faster than you can say «please.» There are good reasons for having a little more than you technically need in your checking account, and this is one of them. Your friend owing money on your behalf and having to beg and plead with you for it is not good for your friendship in the long term.