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 have no doubt that I would prefer to always follow a specific pattern and never win, rather than changing the set once and see how it wins. But, although my father used to play always with the same set of "lucky" numbers (he never won) I prefer to choose random numbers instead, so there is nothing to regret because I have no special attachment to any set that could win and, therefore, no regret.