When beautiful and free-spirited Skyler Dayton wanders into The Stacks, a small, family-run bookstore owned by Gavin Dewitt and his brother, Stuart, looking for a self-help book on relationships, no one expects this to be the beginning of the most unexpected chapter of their lives. In the series opener, Skyler enlists the bookstore gang's help in ending her relationship with her philandering rock-star boyfriend while Gavin begrudgingly asks Skyler to return the favor to make his ex-wife jealous.

Skyler tells everyone in the bookstore that she loves them, but not Gavin. Harold thinks it's because she's infected with a life-threatening illness, while Katrina thinks she just wants money.

Skyler throws Katrina a Western-themed birthday party to attract the attention of a handsome customer.