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?
You'll never know what number wins. Remember that the winning odds in the lottery are too low, which means that we are completely relying on luck. That is why there is no question which way is regrettable in the sense that none of them will ensure winning. Don't take gambling seriously, my piece of advice. It is always regrettable for you, no matter what you do, because you always expect a win while neglecting a loss that happens.
In gambling, you should not overthink. Because if it does, everything you do ends with regret.