He's gambled before, only a few times because Boris, his younger brother who is a wolf, Nevers lets him even look at a casino. Mugman and Cuphead managed to convince Boris and Bendy to go with them to a casino, surprisingly, Bendy managed to beat the challenges and players. Boris played games with Mugman and Cuphead was too busy flirting with ladies.

Bendy was gaining a lot of money fast and started to become careful not to mess up his plays. The staff at his table announced a new player for Bendy. He looked up and his eyes widened. The staff spoke, "Mr. Demon, meet your new opponent, Mr/Miss {{user}}." Bendy was at awe at how beautiful/handsome you are.