Every Song Taylor Swift Wrote About The Men In Her Life Explained

When Taylor Swift released her re-recorded album, "Red (Taylor's Version)," in November 2021, conversation picked up once again about several songs that fans have long felt were about some of her ex-boyfriends. "I wonder if there are people who might think that they were the one you were singing about — if it's easier or far, far worse for them 10 years later," host Seth Meyers asked the singer-songwriter on "Late Night." Swift's response? "I haven't thought about their experience, to be honest." Ouch. Meyers commented what everyone else was thinking: "I think that's the biggest burn."

While appearing on "Jules, Merrick & Sophie" back in 2014, Swift admitted that she does write songs about her past relationships, but noted, "I have a really strict personal policy that I never name names." This, of course, only added to those fan conspiracy theories, but as Swift added, "Anybody saying that a song is about a specific person is purely speculating." The Grammy winner also had strong words for any critic who thought she "just writes songs about her ex-boyfriends," saying, "I think frankly that's a very sexist angle to take," before explaining that several male artists like Ed Sheeran and Bruno Mars also write "songs about their exes, their current girlfriends, their love life, and no one raises a red flag there."

From famous celeb couplings to unrequited crushes to teenage romances, this is every song Taylor Swift wrote about the men in her life explained.

In a 2013 interview with Vulture, Taylor Swift admitted that most of her album, "Red," was about one particular ex-boyfriend. Based on the timing of when she dated actor Jake Gyllenhaal for a few months in late 2010, most people have assumed certain tracks were written about him, including hit singles like "We Are Never Getting Back Together" and fan-favorite ballads like "All Too Well." 

While Swift never named names, she told the outlet that this particular guy reached out after listening to the album, allegedly saying, "That was a really bittersweet experience for me. It was like going through a photo album." According to Swift, their relationship was "a love that was wonderful until it was terrible, and both people got hurt from it — but one of those people happened to be a songwriter."

Almost a decade after its original release, "All Too Well" made a searing comeback with both a re-recorded version and a 10-minute version. That latter features lyrics scrapped for the original recording like, "You said if we had been closer in age, maybe it would've been fine / And that made me want to die," which may reference Swift and Gyllenhaal's nine-year age difference, per Genius. This also became the longest song ever — at 10 minutes and 13 seconds — to top the Billboard Hot 100 chart. "I'm so proud of this song and the memories I have with you guys because of it," Swift tweeted in response to the honor. "You truly chose this one."

For her first role on the big screen, Taylor Swift appeared in the 2010 romantic comedy, "Valentine's Day," playing Taylor Lautner's on-screen love interest. At the height of his fame for playing werewolf Jacob in the "Twilight" movies, Lautner reportedly started dating Swift in real life once the cameras stopped rolling. 

While hosting "Saturday Night Live" in 2009, Lautner addressed the rumors surrounding his relationship with Swift and what it was like being onstage with Swift when Kanye West infamously interrupted her victory speech at the MTV VMAs. However, the romance only lasted for three months and allegedly ended in December 2009 after Lautner flew to Nashville to celebrate Swift's birthday. According to a source cited by Us Weekly, Lautner reportedly "liked her more than she liked him" and "went everywhere he could to see her, but she didn't travel much to see him." 

"Back to December" from Swift's 2010 album, "Speak Now," talks about breaking up with an unnamed ex. With lyrics like, "Standing in front of you, saying I'm sorry for that night" (via Genius), she also sings, "I miss your tan skin, your sweet smile." In an interview to promote "Scream Queens," co-star Lea Michele probed Lautner about whether or not Swift wrote a song about him. "That's what she does. She writes songs," Lautner simply said, before finally conceding that the song was called "Back to December."

While Taylor Swift attended Hendersonville High School in Tennessee, she reportedly linked up with her classmate Jordan Alford — before he moved on to another classmate named Chelsea, whom the Daily Mail reported "would later become his wife."

"We were kind of good friends at school, later not so much. She dated him, that's why," Chelsea told the outlet about their teenage years with the music superstar. She went on to claim that Swift and Alford dated as freshmen in high school, and the Grammy winner later wrote about the situation in "Picture to Burn" off of her debut album. According to Chelsea, Swift's bestie at the time, Abigail Anderson, apparently told her that the song was about Alford. While she claimed to not care that her husband was the subject of the song because it was a long time ago, Chelsea still wanted to set the record straight about one particular lyric: "I'm not a redneck! She makes me look like some redneck! But other than that we just thought it was kind of funny."

Chelsea also recalled that, after Swift's debut album dropped, she and other former students tried to decipher all the different lyrics, saying, "We know other people she wrote songs about. That first record was a game, like, 'OK, which one is this about? OK, did they even date?'" Other former classmates have also alleged that the music video for "Picture to Burn" contains several references to Swift and Alford's relationship, per Teen Vogue.

Thanks to TikTok, Taylor Swift's song "Love Story" received a second life in 2020 as a viral hit on the social media platform, Rolling Stone reported. But the resurgence may have been a painful reminder for the tune's alleged subject. According to Genius, the track may have been about her exes Joe Jonas or Martin Johnson — Swift reported dated the latter, who was the lead singer of the band Boys Like Girls, back in 2008.

As reported by Radar, Johnson apparently had a crush on Swift after the two worked together on the song "Two is Better than One." But people close to Swift allegedly told her a relationship would be a bad idea. A source claimed that Swift was also "head over heels for Martin, but her team didn't really feel that he was a good influence on her or her image." As a result, Swift was reportedly "pretty much forced to end things," with the insider adding, "She sort of broke his heart." The same source alluded to warning flags that her team may have seen. Around that time, Johnson was reportedly "battling some personal demons." 

Another song that may be about Martin is "White Horse," which is also off of "Fearless." Swift told Billboard that the ballad was about being optimistic for the future with a special someone, noting that "then there is that moment where you realize that it is not going to happen." According to Vulture, "Breathe" and "If this was a Movie" are also rumored to be about the alleged connection between Swift and Johnson.

While she was touring in 2008, Taylor Swift caught feelings for her one partner on the road, which she detailed in "Hey Stephen" from her second album, "Fearless." Telling Access Hollywood that "the song is actually about a guy who I had a crush on and never told him," she added, "So I wrote everything that I was thinking down in the song instead of telling him." 

The person in question was likely Stephen Barker Liles, who was in the band Love and Theft that opened her shows. In the album's liner notes, Swift wrote that the hidden message to "Hey Stephen" was "Love and Theft," per Genius. In an interview with The Boot, Liles claimed that he first heard about the song from Swift herself, admitting, "She doesn't really write very many nice songs about guys. So I was very relieved when it turned out to be a nice song, and it's actually one of the nicest things anybody's ever done for me." 

Liles also confirmed that Swift was upfront with him about the song and told Access Hollywood that "she invited us to go with her at midnight to pick up the record ... and listen to the track." Later, Liles responded to Swift with his own song called "Try to Make It Anyway." In the lyrics, per Genius, he alludes to Swift with lines like, "The curly hair and the cowboy boots / How could anyone get over you?"

Around the release of "Speak Now," Yahoo! Music Blogs pieced together the clues in Taylor Swift's song "Enchanted," starting with the hidden message, "Adam," in the album's liner notes. Swift also explained that she used the word "wonderstruck" in the song lyrics deliberately, which pointed to Adam Young. Swift once had a crush on the singer, better known for his stage name Owl City. She also happened to attend one of his concerts at the Bowery Ballroom in Manhattan. 

"It was about this guy that I met in New York City, and I had talked to him on email before, but I had never met him. And meeting him, it was just this overwhelming feeling of: I really hope that you're not in love with somebody," Swift said about the lyrics. She explained that, on her way home from that first meeting, she remembered "sitting there thinking, am I ever gonna talk to this person again?" Swift recalled having a "feeling of pining away for a romance that may never even happen, but all you have is this hope that it could, and the fear that it never will."

For his part, Young wrote in a blog post that he was "honored" Swift wrote a song about him, per BuzzFeed. The Owl City singer added that after listening to the record, "I was lost for words and utterly smitten. I couldn't stop smiling." In response, he released a cover version of "Enchanted" on Valentine's Day in 2011, per Genius.

During "Taymerica" — one of Taylor Swift's epic Fourth of July parties held at her house in Rhode Island — the singer hosted famous guests like Blake Lively and Ryan Reynolds. She was also spotted holding hands with British actor Tom Hiddleston, a source cited by People claimed. The rumor that the two were dating only became stronger when Hiddleston wore a tank top that said "I [heart] T.S." The romance may have started at the 2016 Met Gala in New York, when the pair were seen dancing together. Swift was dating Calvin Harris at the time, but their relationship ended the following month, People reported. 

Sadly, Hiddleswift split up after three months together as an official couple, and Swift seemingly wrote about these back-to-back romances in her song "Getaway Car" from her album "Reputation." Per Genius, Swift's lyrics reportedly "[liken] her rebound relationship with Tom Hiddleston to a 'getaway car' ride used to get away from a crime scene, or her failed relationship with Calvin Harris." Meanwhile, the music video for "Look What You Made Me Do" features a callback to her former actor beau: In one scene, a bunch of dancers are all wearing shirts that read, "I [heart] TS."

Years later, Swift wrote the song "Long Story Short" for her 2020 album, "evermore," which is about her public ups-and-downs. According to Genius, the following lyrics, "Clung to the nearest lips / Long story short, it was the wrong guy," are likely about Swift quickly linking up with Hiddleston after Harris.