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| "I Swear" by All-4-One | |
| The song Chris sings in the mirror before Jamie's graduation party. | UK US |
| "Into Your Arms" by The Lemonheads | |
| Plays in the background of Jamie's party. | UK US |
| "Hip Hop Hooray" by Naughty By Nature | |
| Chris sees Jamie dancing to this song with the popular people in her garage. | UK US |
| "And the Radio's On" by Daisyhaze | |
| Plays in the background of Jamie's party. | |
| "Jamie Smiles" by Chris Klein | |
| Dusty Dinkleman tries to play Jamie the love song he's written for her. | |
| "Love From Afar" by Anna Faris | |
| Sung by Faris' character Samantha James at the recording studio. She dismisses being labels as "bubblegum pop" and insists on playing the guitar while singing. | US |
| "Forgiveness" by Anna Faris | |
| Sung by Samantha at various points during the film, the first being right after she finishes making out with Chris and she continues playing it into the next scene on her jet plane. | US |
| "Catch My Disease" by Ben Lee | |
| Chris returns to the Maple bar. | UK US |
| "When It Goes Around, It Comes Around" by Reed Foehl | |
| Chris sees Jamie for the first time in ten years. | |
| "Hackensack" by Fountains of Wayne | |
| Chris looks through old pictures of him hanging out with Jamie in high school. | UK US |
| "Big Winter" by Robbers on High Street | |
| Chris heads over to the old Palomino place for his day-date with Jamie. Jamie's Dad is setting up their Christmas decorations, which he says are the best display in the state. | US |
| "La Gazza Ladra (The Thieving Magpie)" by Gioachino Rossino (Zagreb Festival Orchestra) | |
| Chris gets mad enough to be better at hockey and shoves kids out of the way and hits a slapshot that comes back in his face and knocks him out. | |
| "Our Love Can Do Miracles" by Aaron Zigman | |
| The music from the movie when Chris, his mom, Jamie and Dusty go see The Notebook. | |
| "Twilight Zone" by 2 Unlimited | |
| Chris drives Jamie home and plays their old mix tape from 1995. | |
| "It's the Most Wonderful Time of the Year" by Jonathan Palmer | |
| Samantha wrecks Christmas and the Palomino holiday decorations. | |
| "Eyes" by Rogue Wave | |
| Jamie gets dressed in the Branders' bathroom and hops into bed with Chris, who's too scared to make a move; repeated later as Chris heads back to Jersey to apologize to Jamie. | US |
| "Waiting on a Friend" by The Sights | |
| Plays when Chris waits for the bus but the bus driver kicks him off ten seconds later for being inappropriate. Continues into the next scene at the Maple as a drunk Chris finally tells Jamie she was a tease in high school. | US |
| "I Swear" by All-4-One | |
| End credits song #1. | UK US |
| "Forgiveness" by Anna Faris | |
| An over-produced remixed version (including many sound effects) appears as the second song in the end credits. | US |
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