Jimmy Boner, a 20-something slacker living with his parents, is given an ultimatum by his wicked stepmother to find a job and move out within 3 months after he accidentally walks in on her book club meeting wearing nothing but an iPod. Jimmy scrambles to find a job and lands an interview at a rundown, overworked accounting office where he meets Ivana, a recently-demoted corporate ice queen with whom Jimmy falls instantly in love. Through a miracle of fate, Jimmy gets the job despite having no marketable skills and puts his nose to the grindstone, working grueling hours and enduring Ivana's constant disappointment, in the hopes of impressing her and garnering her affections. Chaos, hilarity, and triumph ensue as Jimmy seeks to gain independence and find true love.

When Hollywood star Helena Harris (Diane Neal) films her newest movie, “This Magic Moment,” in the small town of Stone’s Throw, she strikes up an unlikely friendship with local video store owner Clark Gable (Travis Schuldt). Helena, who recently broke up with “This Magic Moment” co-star Roberto Molinez (Vincent Spano), asks her new friend Clark to pretend to be her love interest in order to make Roberto jealous. Clark agrees and in exchange, Helena helps him pursue his screenwriting career. While this agreement benefits both Clark and Helena, it also complicates the relationship between Clark and his newly single ex-girlfriend, Emily McIntyre (Alaina Huffman). As the director Doyle Duncan (Charles Shaughnessy) begins to wrap production, Clark finds himself caught between his admiration for the famous beauty and his feelings for former high school sweetheart. With whom will he find his happy ending?