I have never lost money in particular to gambling so big that I ever regretted it. Gambling are to be done with one mind and I think that should also be with the amount that one can afford to lose. Gambling recklessly will only amount to losing much money you won’t be able to account for. If you’re gambling and don’t want to lose a large amount of money, then gamble responsibly by dividing furthermore the money set aside for gambling. Then take each portion and risk the amount. Play as much as you can as long as your money is not exhausted, if you’re not lucky in one game, you’ll be lucky in another which will help to recover your losses in the other games you’ve lost.
If you've never regretted big losses, it means you have a responsible approach that has saved you from making foolish decisions. To get to that point, I personally had to make a few bets that I later regretted. Another challenge was that once, I got lucky and won a big bet when I decided to go all-in to recover my losses. Of course, after that, I tried to do it again and lost. It's not a practice worth repeating, you might get lucky once or a couple of times, but the final outcome is predictable.
I regretted using my tuition fee to gamble just because I thought that I cam double it. It didn't end well for me since I couldn't meet up with the payment and that made me get an extra semester in school. Sometimes, we need to ne careful with our decisions when gambling so that we don't end up putting ourselves in a deep mess.