Things aren't going well for New Jersey high school student Hal Hefner (REECE DANIEL THOMPSON). Not only have his parents, Juliet (LISBETH BARTLETT) and Doyle (DENIS O'HARE) split up, and his kleptomaniac brother Earl (VINCENT PIAZZA) constantly belittles him (usually by calling him by various girls' names), but he's also a stutterer.
Accordingly, he's shocked when Ginny Ryerson (ANNA KENDRICK) suddenly invites him into her universe. That isn't because she's pretty and he doesn't seem her type (although both are true), but mainly because she wants him to be her new partner on the debating team at Plainsboro High School.
Since her former teammate, Ben Wekselbaum (NICHOLAS D'AGOSTO), abruptly quit the team after a disastrous performance at the last championships, Ginny needs a replacement and convinces Coach Lumbly (MARGO MARTINDALE) that she can mold Hal into a champion debater. Accordingly, and as Juliet starts dating Judge Pete (STEVE PARK) and eventually has him move in with his teenage son, Heston (AARON YOO), Hal tries his best to overcome his speech impediment.
When Ginny shocks everyone by transferring to another school, Hal is upset because he thought he was making process, not just with debating, but also romantically with her. Thus, when not practicing for the upcoming championship, he spends his time across the street from Ginny's house in the bedroom of young Lewis (JOSH KAY), hoping he can see what she's up to, particularly when it appears she's gotten friendly with her new debate team partner.