In a strange reversal of fortunes, Dee Dee's charmed life seems to hit an unlucky streak at every turn while, ironically, the usually pessimistic Mona's life becomes auspicious from one moment to the next. When Dee Dee starts doubting herself after failing her assigned mock-court competition at school, with Mona's help she manages to regain her waning confidence by confronting a crooked businessman.

After Dee Dee bests her at an online word game, Mona grows frustrated by the fact that she always loses to her sister. She becomes determined to beat her at something, and sees her opportunity when Dee Dee organizes a poker party for one of her law school professors. Their mothers decide to crash the event, where Phyllis winds up winning Big Dee Dee's wedding ring in the pot. Meanwhile, Adam tries to get access to a copy of Spencer's personal music playlist.

In the hopes of getting closer to Phyllis, Dee Dee sets her up with her bitter divorced professor. However, the relationship soon fizzles, and the professor seeks revenge against Phyllis by turning her in for having too many cats. Phyllis blames Dee Dee, whose efforts to correct the situation only wind up making it worse.