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's old rival Nikki Foos attempts to use Stuart to get even with her.

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 reunites with an old friend, Eve, who she hasn't seen in a very long time. To her surprise, Eve looks completely different than she did last time they crossed paths, and is planning a wedding. Eve then asks Skyler to be her maid of honor.

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

Skyler thinks that Harold is lonely, so she attempts to fix him up on a date. Meanwhile, Katrina has a run-in with an Asian health inspector who thinks she's a racist.