An international mix of "Teardrops on My Guitar", included on the non-US edition of Swift's second studio album, Fearless, was released as a single in Europe in May 2009.

Despite its country radio release, music critics disputed the genre classification and categorized it as pop or soft rock.

Reviews of "Teardrops on My Guitar" complimented Swift's vocals and songwriting for earnestly portraying teenage heartbreak.

In the US, the single peaked at number 13 on the Billboard Hot 100, was Swift's first entry on the Pop Songs chart, and was certified triple platinum by the Recording Industry Association of America.

Trey Fanjoy directed the music video, which features Swift as a girl who is heartbroken when she discovers that her love interest is in a relationship.

Swift was inspired to write "Teardrops on My Guitar" about her experience with a boy named Drew Hardwick, a classmate of hers whom she had feelings for.

[4] Two years after the album's release, as she was leaving her house to attend a Nashville Predators hockey game with Kellie Pickler and Carrie Underwood, Hardwick appeared at her driveway.

[3] "Teardrops on My Guitar" was released to US country radio on February 20, 2007, by Big Machine Records as the second single from Swift's debut album.

Perone cited the song as Swift's songwriting ability to draw on diverse musical styles and regarded the "teardrops on my guitar" image one of the album's most memorable lyrical details.

Holland continued, "Yet this is the channel to market she has chosen, and so she has to be prepared to hear complaints about the way that trademarked Mutt Lange guitar whine has been married to her bright shiny pop songs in order to get them onto CMT, GAC, and country radio.

"[26] Fiona Chua of MTV Asia said "Teardrops on My Guitar" demonstrated that with Swift, "what you hear is what you get", and selected it as one best cuts on Fearless.

[22][note 1] Deborah Evans Price of Billboard stated that "Teardrops on My Guitar" showcased the same qualities as "Tim McGraw" (2006) – solid gifts of songwriting and time-halting earnest and pure voice.

[23] Chuck Taylor, also of Billboard, reviewed the pop version release of "Teardrops on My Guitar", and stated it was a "beautiful mainstream intro to an artist whose rise is ably exemplified by her last name.

"[20] An uncredited review from Rolling Stone attributed the track to be one of the reasons why Taylor Swift was so commercially successful.

[27] Jon Bream of Star Tribune believed the song was in attempt to empower high school- and college-age females by confronting males.

[30] In the United States, "Teardrops on My Guitar" peaked at number 13 on the Billboard Hot 100 chart dated February 23, 2008.

[35] The single was certified triple platinum by the Recording Industry Association of America (RIAA) in April 2014, for surpassing three million units based on sales and streaming.

Swift had been fond of Hilton's music as well as acting on the television series One Tree Hill and the film Walk the Line (2005).

By the song's bridge, Swift's character witnesses the male lead kissing his girlfriend as she watches despondently.

[47] She performed "Teardrops on My Guitar" as she opened for Rascal Flatts on several dates, from October 19 to November 3, 2006, included on the Me and My Gang Tour (2006–07).

[64] Since completing promotion for Taylor Swift and its corresponding singles, Swift has performed "Teardrops on My Guitar" as a duet with English rock band Def Leppard on CMT Crossroads, the episode was released as a DVD exclusively through Wal-Mart stores in the United States,[65] Clear Channel Communications's Stripped,[66] at the 2009 CMA Music Festival,[67] at the 2009 V Festival,[68] and at the Australian charity concert Sydney Sound Relief.

He stated, "Taking a cue from her pal Miley Cyrus, Swift embellishes hits such as 'Teardrops On My Guitar' and 'Love Story' with a lot of flashy production in concert.

"[73] Brandy McDonnell of The Oklahoman, who attended the March 31, 2010, concert at the Ford Center in Oklahoma City, believed "Teardrops on My Guitar"'s music video heavily influenced the setting and role she enacted in the performance.