Salem bets Zelda, Hilda and Sabrina at a big poker game in the Other Realm against Diamond Dave and loses, so now the girls have to serve Diamond Dave for the next twenty years. Zelda will be his cook, Hilda will be his maid and Sabrina will be his personal assistant and is keen to the idea once he reveals that she will get to drive his porsche. In order to get out of this deal, they brew up a sleeping potion, but they are caught when Diamond Dave orders Hilda to try his food and the punishment is to clean the sewers. Sabrina doesn't take this and bets they will stay forever if they lose a game of Chutes & Ladders, a game that Sabrina has never lost. As Sabrina and Diamond Dave advance in the game, Sabrina starts to lose. When a final roll of the dice declares Diamond Dave the winner, Hilda, who is still having a reaction to the Sleeping Potion stumbles in and Diamond Dave rudely tells her to exit. So the dazed Hilda tells him that she spit in his grotto and Diamond Dave makes another rude remark calling her "Aunt Tipsy". Hilda then states to have never liked him and that she is annoyed by his chin cleft before punching him unconcious. While Diamond Dave is out it is revealed that he cheated Sabrina with dice that had 6 on all sides, Salem declares he must have been cheated as well and they make their escape. Back at home Hilda and Zelda decide to let Sabrina drive Diamond Dave's porche to the Celtics game with Harvey. As Sabrina pulls up everyone starts to gaze and they all prefer to take the bus over Libby's available shotgun offer. Sabrina states to Libby that she'll try not to gun it when she passes her on the thruway and drives off.
- Melissa Joan Hart as Sabrina Spellman
- Nick Bakay as Salem Saberhagen
- Caroline Rhea as Hilda Spellman
- Beth Broderick as Zelda Spellman
- Nate Richert as Harvey Kinkle
- Jenna Leigh Green as Libby Chessler
- Edward Albert as Diamond Dave LaRouche
Uses of Magic
- Valerie and Mr. Kraft do not appear in this episode.
- This episode marks the first time Sabrina cackles over a cauldron. She previously commented on how cool it was when her aunts did it in the Season 1 episode "Trial by Fury."
- The title is a pun on the game show You Bet Your Life.
- At the end of Opening Credits in this episode, Sabrina is wearing a strawberry outfit and says "Pick me! Pick me!"