The accompanying video to "Teardrops on My Guitar" was directed by Trey Fanjoy, who directed the video for "Tim McGraw". Swift decided to film the video with Fanjoy as a result of how positive the experience was when filming "Tim McGraw". She appreciated all the preparation techniques that she taught her and stated, "You have to remember the people who were good to you in the beginning". Swift said the video centered around unrequited love.Some of Swift's associates first believed the video should have been set in a prior era. They then though about filming the video at a large city. However, Swift wanted to go back to basics and keep the song's integrity by filming the video in Nashville, Tennessee.American singer and actor Tyler Hilton portrayed Drew. He was cast because of prior interactions with Swift.They had a mutual fondness for each other's music. Taking into account his acting on the television series One Tree Hill and the film Walk the Line (2005), Swift asked him to participate in the video after he attended and performed at one of her concerts.Swift chose Hilton primarily because he accurately represented Drew, a cute guy that is oblivious to the fact someone has feelings for him.The video was filmed in one day in March 2007 at Hume-Fogg High School; the drama room was transformed to simulate a bedroom for the performance scenes.The video commences with Drew asking Swift, "Hey, are you gonna go to the game on Friday?" Swift responds, "Well, I don't know. I was thinking about it. Why?" He then admits it was just curiosity, informs Swift about a girl he met, and walks away. The video then transcends to Swift, wearing a long aquamarine evening gown, lying beside an acoustic guitar on a mattress in a bedroom. She performs the song until the scene transitions to Swift and Drew at the library, where he parodies a novel and she chuckles. The librarian requests for the two to maintain silence, so they converse quietly. Afterwards, Swift is in a chemistry laboratory, where she is mixing substances. Distracted by Drew approaching her, she accidentally pours too much of one substance and causes it to spill. They both rapidly attempt to clean the mess generated. As the song approaches its bridge, Swift and Drew walk towards each other, both smiling, but Drew then kisses his girlfriend, as Swift watches in agony. The video again transcends to the performance scene, where it concludes. Cut-scenes feature Swift lying on the mattress, crying, and standing beside a fireplace in the bedroom. The video received a nomination for "Number One Streamed Music Video" at the web-hosted 2007 CMT Online Awards, but lost to Sugarland's "Stay" (2007).The video received a nomination for MTV Video Music Award for Best New Artist at the 2008 MTV Video Music Awards, but lost to Tokio Hotel's video for "Ready, Set, Go!" (2007).