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.

After Dee Dee learns that her mother's co-star in a new play is engaged to Dee Dee's idol, esteemed attorney Maxine Shaw, Dee Dee sees an opportunity to atone for a bad interview she once had with the woman. However, Dee Dee believes she has lost her chance after Big Dee Dee (who had to finance the play to ensure she could star in it) gets Max's beau fired because she fears he will take attention away from her. Meanwhile, Mona must find a way to rein in her co-workers after Kai is delayed and leaves her in charge of a company retreat at a resort.