Let's say when gambling, you follow a specific pattern. Let us use lottery for example. You bet on the same specific set of numbers. What would be more regrettable? Betting on the same set of numbers for the rest of your life and not winning or... changing up the set you bet on only for your old set to win?
Basically, would you rather bet on the same thing again and again then regret not exploring more or explore different kinds of bets then miss out on a win?
I am not sure there is anyone who would consistently follow thesame pattern all his life when that pattern is not giving the desired results. After a few unproductive attempts, they will switch to a different pattern.
The second option is more regrettable. It would have been better that the first pattern didn't win at all that for it to become the goal immediately after switching.
To avoid feeling so hurt with scenarios like this, simply gambling with what one can afford to lose will be the best option. Things like this happen alot in gambling, but we can't hurt ourselves simply because we lost.