That can happen if one becomes addicted to playing games of online poker or blackjack.

Debt is the primary driver in Animal Crossing and Recettear.

Most sports video games, that have a franchise or owner mode are ones you could unwisely manage your team, and be in the negative.

I think I’ve lost money, on the ancient “Sim City” before.

Slot machines on-line!

Microsofts Solitaire you can go into negative payouts if you lose enough.