Inspired by a phone call that Taylor overheard between her friend and his girlfriend, You Belong With Me tells the story of an insecure person in love with someone they feel is out of their reach. Released in her second studio album, Fearless (2008), the song is a country pop tune and its music video, directed by Roam White, won Best Female Video at the 2009 MTV Video Music Awards.

The video features Swift playing two characters: an ordinary girl, who is secretly in love with her male friend and neighbor, and a popular girl, who is his girlfriend. Throughout the story, we see various moments of frustration from the main female lead, as she witnesses different acts of mistreatment towards her love interest. She finally gathers the courage to declare her feelings to her friend, and we get to see them together in the end.