What have you lost the most money on and still regret it to this day?
Have you ever gambled or bet and still feel guilty?
All in all, my answer is NO.
I only gamble with what I can afford to lose, nothing more.
I don't expect big wins from gambling, but if they occur, it could be a bonus while enjoying the game.
Keep in mind that gambling never guarantees payouts or profits, so having a clear strategy to secure gains is very important. You must implement a stop-loss to avoid chasing losses.