Since the early beginnings of Taylor Swift's songwriting, she has employed the confessional style of the diarist in her lyrical tributes to the joy and heartbreaks of youth. All of Taylor Swifts songs, rich in melody and unique in the seemingly effortless craftsmanship of their catchy bridges, owe much of their quality to the feckless honesty of their lyrics. In keeping with many great artists, Taylor Swift's songs transcend the standard outlay of the crises of youth. Hers is not the mere portrayal of the lovelorn. With a striking honesty similar to that of Janis Ian and Brian Wilson, Taylor Swift gives dramatic importance to the otherwise mundane elements everyday life as illustrated by her past relationships.

Due to the incredibly quick reception of her work by the public, almost all of Taylor Swift's songs have become closely associated with her past dating history. Though she has stated that many of the subjects she sings about are fictional creations rooted solely in observation, she has also very clearly indicated which songs are personal documentations of past relationships. The subjects of these songs range from high school romances to more recent liaisons with men who share with her, at various levels, a highly public profile that quickens the interest for details behind the meaning of her lyrics.

Of her early personally tailored tributes to past boyfriends, a few of the subjects remain anonymous. Taylor wrote "Tim McGraw" when she was a freshman in high school. It recalls the time she spent with a boy named Brandon Borello and was written as a parting gift to him when they broke up on his departure for college. She hoped that he would remember her and the time they spent together every time he heard a song by Tim McGraw. "Picture to Burn" is a song about a narcissistic man who, despite their never having a relationship, inspired her to write these lyrics about his openly selfish, self-serving nature. She refers to him as the "redneck" and his real name is not known. In 2007, she wrote "Teardrops on My Guitar" about a classmate named Drew Hardwick. Her affection for him was unspoken and, due to his love for another girl, her interest remained secret until "Teardrops" was published. Realizing the song was written about him, Drew contacted Taylor and asked her out, but, considering his proposal too opportune, she rejected his offer. At the age of sixteen, she wrote the song "Should've Said No" about an unfaithful boyfriend who, it has been deduced, may have been her first lover. In several introductions to the song in concert, she has given his name as "Sam". Nothing else is known about this early excursion into heartbreak.

Since 2008, with the release of her first million-selling CD, the men in her life have been widely known and the facts behind her songs about them are more easily discernible than those of her earlier compositions.

In the summer of 2008 she met Joe Jonas, of the Jonas Brothers. They dated through the summer of 2009, during which time she noticed a reduction in his affections, the cause of which she would discover to be his interest in Camila Belle, star of the remake version of “When a Stranger Calls”. Particularly hurtful, as Taylor confessed on the Ellen Degeneres show, was that Jonas broke up with her during a "27 minute phone call". The song "Forever and Always" documents her sadness and frustration as Jonas' feelings for her waned. She wrote two more songs about Jonas after their breakup was final, "Last Kiss” and "Better than Revenge", the latter an uncharacteristically venomous commentary on Camila Belle's new affair with Tim Tebow.

In the fall of 2009, she began her relationship with Taylor Lautner after they met on the set of their movie “Valentines Day”. Soon to be known as "Taylor squared", the couple dated through early 2010. It was a strong bonding, however Taylor Lautner’s feelings for Swift exceeded those she had for him and this time it was she who initiated their breakup. Her song "Back to December" contains her feelings of remorse and her need to apologize for having broken his heart. The song is, in effect, a plea for his forgiveness. Many have interpreted the final lyrics to favor a potential reunion.

Her romantic tryst with John Mayer is documented in the song "Dear John". Their time together was very short and it is rumored that his philandering habits were their downfall. Twelve years Taylor’s senior, John Mayer has responded harshly to the song’s accusatory lyrics. He maintains it was Taylor who misunderstood their connection as more than a casual fling. They harbor extreme resentment toward one another and no longer speak.

In all of Taylor Swifts songs there has never been such a deep expression of the hurt she felt when Jake Gyllenhaal rejected her. Jake Gyllenhaal, of "Brokeback Mountain" fame and the subject of her best-selling never getting back together song, was Taylor’s next romantic excursion. She has expressed several times openly the magnitude of her love for him and how badly heartbroken she was when he broke up with her. Jake Gyllenhaal, notoriously insistent on his privacy, expended vast amounts of money to ensure his relation with Taylor did not become a media spectacle. He purportedly once rented an entire theater for a night so they could see a movie together. She and he attended Thanksgiving festivities at his parents’ home. Gyllenhall’s heartless method of ending their affair was with a text mail. The reasons he gave were based on his concern over the unending publicity of their union and that he was sensitive to his being eight years older than her. The never getting back together song, “The Moment I Knew” and “Girl at Home” are all about Gyllenhaal.

Taylor's recent relationship with Conor Kennedy ended quickly, possibly due to his youthful rejection of her need to tie him down. The son of Robert F. Kennedy, Connor is eighteen years old, three years Taylor’s junior. Her need for long term commitment did not mesh with the vistas of experiences he could, as a Kennedy, more likely obtain in a romantically unfettered state. As of yet, there have been no songs Taylor has published regarding her dating history with Conor Kennedy.

Most recently Taylor Swift has been seen going out with Harry Styles from One Direction. That didn't last long though. Pressure from the other members of One Direction allegedly led to the Harry Styles breaking it off.