When Taylor Swift was interviewed by Ellen DeGeneres on her show in October of 2012, the comedian dared the country superstar to play a game of “Was He Your Boyfriend?” Swift was instructed to ring a bell if she had dated the man whose picture came up on a slideshow, but Taylor ended up not playing and instead looked terribly uncomfortable. She explained, “I don’t want to! Because they’ll send me angry emails, and I don’t want to get them!” Well, Taylor may have appeared not to be at ease talking about her exes in public, but she sure has attracted a lot of attention by making several of them the inspirations for her songs. In fact, although not solely because of her colorful love life, Swift has sold more than 30 million albums and more than 80 million digital single downloads worldwide.
Here are ten men, some her exes and some not, that Taylor Swift has been rumored to have written about in her songs, which have certainly taken the world by storm:
10. Drew Hardwick
Swift actually mentions the name of the boy whom “Teardrops on My Guitar” is about when she sings, “Drew looks at me” as the first line of the song. That “Drew” is Drew Hardwick, a high school classmate that Taylor had developed a crush for. However, Taylor ended up never revealing her feelings to him because Hardwick would often speak to the then-to-be music superstar about another girl he had feelings for, something Swift pretended to be happy for him about. Well, when Teardrops became a massive hit, Drew tried to get in touch with Swift, but a romantic relationship never developed between them.
9. Drew Dunlap
When she was a freshman in high school, Taylor wrote “Tim McGraw” for her boyfriend at the time, a certain Drew Dunlap. The song, which turned out to be her first ever published material, contained Swift’s feelings about how she and Drew had decided to break up because he was going to college at the end of the year. The lyrics contained various things that she felt would remind Dunlap of their relationship, one of them being Taylor’s love of Tim McGraw‘s music.
8. Adam Young
Adam Young, also known as the man behind Owl City (of “Fireflies” fame), never really dated Swift, but he was fortunate enough to have had a beautiful song written about him by her. In a 2011 interview with US Weekly, Adam shared that he considers Taylor “a great person” and that he is “so inspired by her music and the person herself.” He also revealed that he bought Speak Now at midnight when it was released, and was thrilled that he saw his name spelled out in Enchanted‘s lyrics code. Before that, the two had emailed back and forth, and one time Taylor had commented that Adam was the first person she had met who had used the word “enchanted”. It was for that reason that he guessed the song was about him. For his part, Adam recorded this cover of the song, but it seems Swift never responded:
7. Joe Jonas
The late Joan Rivers interviewed the Jonas Brothers when they paid a visit to the Fashion Police set in 2013. The feisty host brought up how Joe Jonas had dumped Taylor via a 27-second phone call, and observed, “You did it over the phone, and you got three songs written about you.” Those three songs are “Forever & Always” from Fearless, “Last Kiss” from Speak Now, and “Holy Ground” from Red. The lyrics of the songs seem to reflect how Swift still values the fond memories of her past with Jonas despite her irritation at the abrupt end of the relationship. There’s one more Joe-related song, however, where Taylor isn’t as sweet and demure; in “Better than Revenge” from Speak Now, Swift almost certainly sings about Camilla Belle, who is believed to have stolen Joe’s heart from Taylor. In Better, swift sings,
She’s not a saint
And she’s not what you think
She’s an actress, whoa
She’s better known
For the things that she does
On the mattress, whoa
Soon she’s gonna find
Stealing other people’s toys
On the playground won’t
Make you many friends
She should keep in mind
There is nothing I do better than revenge
6. Taylor Lautner
The two Taylors fell in love after meeting on the set of their 2010 smash movie, Valentine’s Day. Soon after, the tag “Taylor Squared” was born. Unfortunately, Swift seems to have bungled the relationship, but she publicly apologized to Lautner for it through her 2010 hit song, “Back to December”. In it, she regretfully sings, “So this is me swallowing my pride / Standing in front of you saying, ‘I’m sorry for that night.'” She seems to further reference Lautner in the line “I miss your tan skin, your sweet smile.” Making the song’s subject even more obvious, the Speak Now lyrics sheet for the song contains the hidden message “TAY”.
Intriguingly, in a much-talked about live performance of the #6-peaking Billboard Hot 100 hit during the 2010 American Music Awards, Swift mashed in parts of “Apologize”, seemingly an allusion to the parody video Lautner made for the One Republic song. The heartfelt performance by Swift was listed by Time Magazine as one of the top apologies of 2010.
5. John Mayer
For his 2009 album, Battle Studies, John Mayer collaborated with a then teenaged Taylor Swift on the song “Half of My Heart”, and the two were said to have dated after working on the track. However, the two split up months before Swift’s Speak Now album was released, and it wasn’t too difficult for fans to guess whom “Dear John” was about. Some of its lyrics go, “Dear John, I can see it all now that you’re gone. / Don’t you think I was too young / To be messed with?” Taylor later confirmed that both “Dear John” and “The Story of Us” were inspired by the same person. For his part, Mayer told Rolling Stone magazine that “Dear John” made him feel terrible and that “it was a really lousy thing for her [Swift] to do.”
4. Cory Monteith
Taylor spoke to Yahoo! Music about her 2010 album, Speak Now, and in that interview, Swift talked about her first single, “Mine”. She said that the song was “a confession of some sort” about a guy she hadn’t even dated but whom she had thought was cute. Swift shared, “This is a situation where a guy that I just barely knew put his arm around me by the water, and I saw the entire relationship flash before my eyes — almost like a weird science-fiction movie.” That recounting seems to match a story told by unnamed sources who claim that the “arm being put around Taylor” is exactly what happened between Swift and the late Glee star.
3. Jake Gyllenhaal
Jake Gyllenhaal is perhaps the boy Taylor Swift has written the most about in the songs she has released. “The Last Time”, “We Are Never Ever Getting Back Together”, “State of Grace”, “Girl at Home”, and “The Moment I Knew” have all been rumored to be about the actor. But it is perhaps “All Too Well” that paints the saddest picture of late 2010 and early 2011, when the two were said to be dating. In the track, Swift sings about a scarf that she left at the home of a lover’s sister and how he has kept the scarf despite returning all her other things. The details seem to be clear references to a scarf that Taylor was photographed wearing when she attended a Thanksgiving dinner with Jake at Maggie Gyllenhaal’s Brooklyn home. In fact, in an interview with Good Morning America, Swift revealed that the song was very laborious to write because it started out as a ten-minute song, and she “had to filter it down to a story that could work in the form of a song.”
2. Conor Kennedy
Considering what Taylor has written about of her exes, Conor Kennedy can probably consider himself lucky that the song she wrote about him is entirely positive. The two were reported to have been dating for only a few months, but from the brief relationship was born “Begin Again” from the Red album. In the song, Swift fondly describes falling in love again after going through a failed relationship. More specifically, she sings about a boy who has as many James Taylor records as she does and who throws his “head back laughing like a little kid.” The speculation is that “little kid” is a reference to how Conor is three years younger than Taylor. Moreover, the song was released as a promotional single in September of 2012 and as the second Red single in October of the same year — both are within the period the two were said to have dated.
1. Harry Styles
If Taylor Lautner and Taylor Swift as an item were called “Taylor Squared”, Harry Styles and Taylor were dubbed “Haylor”. And the One Direction star predictably got his own share of songs written about him, too. The first was reportedly “I Knew You Were Trouble” from Red — the title itself seeming to indicate how Taylor felt about Harry after he had cheated on her in 2012. And Swift seems to have kept the Harry song diaries coming with several more songs, this time in her new album, 1989. “Out of the Woods” mentions “twenty stitches in a hospital room,” which appears to allude to a snowmobile accident the couple went through together. Then there’s the hardly veiled “Style”, which she sings to a guy with a “James Dean day dream look” in his eye.
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