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.

When Stuart volunteers to retrieve Skyler's grandfather's watch from her ex-boyfriend Eddie, he ends up getting sucked in by Eddie's charms himself. Skyler attempts to get her mind off Eddie by attending Katrina's knitting group and finds that the company of women is quite different than she expected.