Gavin is distraught when Skyler tells everyone but him that she loves them. Stuart tells a customer he loves her in order to defuse his response to Skyler, but it turns out that the customer actually does love him. Harold overhears Skyler's conversation and believes she's dying.
Skyler's friend Eve arrives in town and shocks Skyler with not only her transformation into a beauty from her former ugly duckling appearance, but also that she's getting married to a rich elderly man.
An old rival of Skyler's shows up under the pretense of apology, but her competitive nature shines through when she thinks that Stuart is Skyler's boyfriend and seduces him. Harold starts hearing buzzing when he tries to write a speech.
Gavin is visted by a member of his former writing group named Crazy Ray who informs Gavin that he's been published. Gavin feels the need to work on his own book and the staff feels the burn.
Gavin arranges a date with a young woman who left an iPod at the bookstore, but after a shared moment learns she's only seventeen. Stuart spots a customer who always uses the bathroom and never makes a purchase.
Skyler tries to play cupid for Harold, introducing him to her mentor. When she flakes, Gavin tries his hand at matchmaking. Katrina comes under the watchful gaze of a health inspector.
Skyler hopes that a Western-themed birthday party will lure a customer that Kat finds attractive. Skyler helps Gavin with his wardrobe and Gavin must enter an impromptu thrift store dance-off to try to regain his lost cowboy boots. Kat and Stuart hook up after her crush doesn't show and Skyler leaves with her own date.
Kat and Stuart's post-birthday party encounter comes out to the rest of their cohorts and Gavin wants Stuart to consult a lawyer cousin to avoid sexual harassment.
Gavin prepares for a gallstone removal surgery. Stuart works to effect Gavin's will. Gavin lets the drugs do some talking with Skyler and confesses his desire to be with her.