Dee Dee tricks Mona into joining her at a singles weekend at an exclusive new hotel. Mona meets a handsome bartender, but Dee Dee repeatedly tries to steer her away from him, claiming that she has her best interests in mind. Spencer and Adam also attend the event, thanks to Adam's successful friend. Spencer enjoys the perks of hanging out with Adam and his friends, but is surprised to discover that people believe he is also gay. Meanwhile, Big Dee Dee convinces Phyllis that her presence in the building and relationship with Glen are driving Mona away.

Mona realizes that she needs to slow down her relationship with Chase after they start spending so much time having sex that it begins to affect her job and other aspects of her life. Dee Dee plans a "legends ball" on behalf of her mother (who is depressed because of her floundering acting career), but finds that none of the invited guests want to attend. Spencer buys a gigantic new truck that soon leaves him financially strapped because he can't afford gas.

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.

Mona convinces Chase to hire Lorenzo as a pastry chef at City Sonoma. Chase become furious with Mona for not informing him that Lorenzo is her ex-boyfriend. Phyllis is bed-rested after taking a fall in the hallway of her apartment building, which Big Dee Dee and Charles happen to own.

While Chase is out of town on a business trip, Lorenzo shares with Mona that he still has feelings for her. Although Mona remains committed to Chase, she begins to fantasize about Lorenzo. Meanwhile, Dee Dee tries to convince Big Dee Dee and Charles to financially support Adam's new career as a stand up comedian. Big Dee Dee quickly agrees when she finds out she can produce his stand-up set.

Mona discovers everyone is hanging out with Chase behind her back. Gus leaves town, leaving Brett in charge of the office. But when Dee Dee's colleagues tell her he is envious of her new responsibilities she tries to keep the peace in the office. Meanwhile, when Mona begins to see a therapist she realizes she has to take control of her life.

In an effort to make up her mind once and for all, Mona decides she wants to date both Chase and Lorenzo. When both men agree she finds herself more confused than ever. Dee Dee meets a new guy but when Brett tells her the relationship won't stand a chance, she sets out to prove him wrong. Meanwhile, Spencer meets a new woman and when she invites a friend to join them on the date he thinks his dreams have come true.