My Happy Ending was shot in Williamsburg, Brooklyn and Harlem, New York City. The video begins with Lavigne running down a street and entering a cinema, where she finds the film playing is a montage of her memories concerning a specific relationship she had. At first, the memories (shown in full color) are happy, depicting Lavigne at the park with her boyfriend, as he hands her a flower and they laugh together. They are also shown goofing off inside a laundromat. However, as Lavigne sings "so much for my happy ending", the memories start to lose color. Lavigne and her boyfriend lie in bed together, as she looks at him and he stares blankly away. The relationship culminates during the song's bridge inside a grocery store, where the boyfriend antagonizes Lavigne, insisting that he talk to her. He grabs her and tries to pull her into his embrace. Fed up, Lavigne turns and pushes him away. She proceeds to run out of the grocery store and down the street, and to a guitar shop where she grabs a guitar and walks to the roof of the building. There, she walks past the unapologetic boyfriend without looking at him. The theater film tears and the memories end, leaving the final seconds of the video as a close-up on Lavigne in the theater as she tries to decide if the break-up is happy after all. In the end, three other girls leave with Lavigne who know about the breakup as they watch from the restaurant.

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