All of the Boys She Loved Before


Caitlin Quinlan

Taylor Swift at Gillette Stadium on May 20th performing “Lover.”

Caitlin Quinlan, Contributing Writer

Taylor Swift’s love stories have always been haunted. The media work like masterminds to find every detail of her life. People outside Swifties usually see her as another famous person who has dated too many men and then goes on to write songs about them. Although Swift’s fans know the men in her life have not shaped her career, she’s done that all alone. Swift has many famous exes from throughout her life; some were revealed to be more controversial than others in a poll conducted on

Beginning in December 2009, Swift and John Mayer were linked as a couple after collaborating on “Half of My Heart.” Mayer was 32, and Swift was 19 then, a 13-year age gap between the two. The relationship only lasted until February 2010, and Mayer was explicitly mentioned with the release of Swift’s new album Speak Now. The song “Dear John” became a hit, with Swift telling the story and emotions she felt during the relationship and break-up with Mayer. She clearly called out their age gap with the lyric, “Don’t you think I was too young to be messed with?” Mayer later mentioned he had never known her feelings on the relationship until the song was released, and he felt “humiliated.” SHS students notably find John Mayer as their least favorite boyfriend, with 42% of 19 voters choosing him.

After Swift released her most recent album, Midnights (3 AM Edition), fans have speculated about the song “Would’ve, Could’ve, Should’ve”: Is it about Swift and Mayer’s relationship? Swift uses the words, “Give me back my girlhood–it was mine first.” Having held back from name-calling exes in songs since the “Dear John” release due to the controversy it aroused, Swift is set to release Speak Now (Taylor’s Version) on July 7th, 2023, with the new version of the popular song “Dear John.”

Mayer isn’t the only infamous Swift boyfriend; the album Red revealed the bad blood between Swift and her actor ex-boyfriend, Jake Gyllenhaal. The song “All Too Well” illustrates their tragic story, including mentioning a red scarf and the heartbreak she faced. Swift has never confirmed the song is about Gyllenhaal. They dated in 2010 for three months, when Swift was 20 and Gyllenhaal was 29. 

In 2021, Swift re-released her Red (Taylor’s Version) album with a 10-minute version of “All Too Well.” Fans were elated while delving deep into the new verses. Continuing the “All Too Well” fever, Swift directed and released an “All Too Well” short film starring young actress Sadie Sink and actor Dylan O’Brien. The movie supposedly represents Swift and Gyllenhaal’s relationship as it started as a whirlwind romance devolving into a dreadful break-up.

Swift’s longest-known relationship was with London boy Joe Alwyn, starting in 2016 and reportedly ending in 2023. Alwyn was the SHS favorite Swiftie boyfriend, with only one vote against him. Swift has written songs about Alwyn in her Reputation, Lover, Folklore, Evermore, and Midnights albums. Unlike all her other past partners, Swift worked with Alwyn to write songs together. They co-wrote songs during Covid together using the pseudonym for him–William Bowery. Swift revealed it was Alwyn in her “Folklore: The Long Pond Studio Sessions” documentary. Swifties were saddened to hear of their split at the beginning of this year, many still denying any truth behind it. 

Recently, a previously unreleased Midnights song called “You’re Losing Me” was exclusively released for download on the Taylor Swift merch store for 24 hours. Fans theorize it’s about Alwyn, with lyrics connecting to songs Swift wrote with him.

Swift was recently reported to be in a new relationship with Matty Healy, the controversial lead singer of the alternative British band 1975. However, sources have reported recently that Healy and Swift have split up due to incompatibility. Healy has been an unwanted boyfriend since their relationship started. Fans were dying to be clean of him. His comments on women and people of color have been derogatory and disrespectful. Healy has not apologized for many of his comments and seems to be fueled by the controversy he creates. Swifties around the globe will be shaking off Healy’s bad karma.