I’ve had very few that I regret. I only gamble with money I can afford to lose and I’m pretty conservative when I do as far as the bets I make. The only one that I can really remember that I regret was a few years ago with a friend. He drives a truck for a living and hates to drive or ride so when he goes somewhere he wants to stay a while.
One night while we were at the casino I was down about $1000 and got down to literally my last $10 in chips. I threw the $10 down on the table and the next shooter (craps) had an incredible roll, about 30 or 40 minutes and hit a bunch of points and numbers. I was $30 or $40 ahead at one point but my friend wouldn’t leave. I stood there and gave back my entire $1000.
It’s not his fault, that’s just what happened. That was many years ago and since I have learned to set win loss limits and to actually stop when I reach them. When I go with him now and he doesn’t want to leave and I get done gambling, I’ll hang out at the bar and play penny slots or go eat.