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 must hit the books to prove her worth when Gavin hires an ultra-competitive new employee and then realizes that only one of them can stay on the staff.

Comments about Skyler being a ""groupie"" come back to haunt Gavin when he proves to be one himself. Meanwhile, Skyler tries to get Katrina in to see her favorite band and Harold tries to make amends for telling Stuart he has no chance of ever being with Skyler.

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.