After throwing together a baby shower for Neil and Janet, Dee Dee becomes concerned by the fact that she is the only person in attendance who is not attached. She begins to question her life and decision to pursue her career so aggressively. Meanwhile, Mona worries that her lack of maternal instinct could have a negative effect on her relationship with Chase. She tries spending time with Drew, and receives some advice from Big Dee Dee.

Mona fears that Chase hasn't made any special plans for Valentine's Day, so she tries to take action. Dee Dee sets Brett up on a blind date in the hopes of curing him of his bad mood concerning the holiday, which stems from a broken engagement. Spencer gets close with a rival music executive whom Mona despises. Adam grows irritated with his Valentine's date, a man with whom he's shared a yearly tryst for the past 10 years.