"First Cut Is the Deepest" February 18, 2008
Kyle takes Jessi on a trip to University of Washington to learn more about Sarah, while she continues to try proving that she is better than Kyle. Meanwhile, Hillary, Lori, and Amanda attempt to book a cool DJ for prom. Declan and Kyle get involved in a bloody fistfight when a college boy tries to punch Kyle. Kyle finds Jessi to be continuing to push herself. Amanda tells Kyle that she accepts the fact that she has to share her boyfriend with other people. Andy and Josh receive couple's counseling from Nicole.