Chris takes Samantha to his mother's house to spend the night and re-engages with his teenage past, including his unresolved feelings for Jamie. Samantha meets Chris' mother and 18-year-old brother Mike (Christopher Marquette) who has an enormous crush on Samantha. At the local bar, Chris encounters some old classmates, including his other best friend Clark (Fred Ewanuick) and his wife Darla (Amy Matysio); he also encounters Jamie, who is working as a bartender to support herself through graduate school to become a teacher. Chris plans to impress and seduce Jamie by having Mike keep Samantha busy during his date with Jamie, but the realization that Jamie's platonic friendship is important to him hampers Chris' plan. During a friendly ice skating "day date", Chris is taken away in an ambulance after injuring himself during a hockey game with Jamie and a trio of kids (who start to share a dislike on him for his inexperience). At the scene, Jamie is reunited with Dusty Dinkleman (Chris Klein), a paramedic and former high school nerd who was also in love with her, while Chris is taunted by all of the kids in town for making them lose the game.