Doug secretly takes $100 from the "emergency fund jar" without Carrie's knowledge and bets it on a race. When he and Deacon win $5000, Doug knows he can't tell Carrie about the big win because she'll know he took the money after she told him not to. Deacon and Doug decide to spend the winnings all in one day of fun by renting a fancy sports car, eating a big steak dinner, and hiring Eddie Money to come to the house to sing for them.
Meanwhile, Carrie is offered a new job from the owner of the firm where she works. Turns out the offer isn't as great as she thought.