A gaming system and method for conducting a wagering game includes a display having a display area showing a poker-themed wagering game. A wager input device receives a base wager to play the poker-themed wagering game. A controller is coupled to the display and the wager input device. The controller is operative to provide a plurality of symbol-bearing objects to form a user-playable hand and award a payoff based on a ranking of the user-playable hand meeting a predetermined criterion. The controller may receive a side wager separate from the base wager from the player to trigger a challenge based on meeting a condition in at least one of a predetermined number of future plays of the wagering game. Additional free challenges may be triggered for the predetermined number of future plays.