In the words of Taylor Swift: “So tell me everything’s not about me, but what if it is?”
Fans of the “Who’s Afraid of Little Old Me?” singer have been on high alert as one of Swift’s famous exes, Jake Gyllenhaal, is hosting Saturday Night Live stage on May 18, 2024, with her pal and Eras Tour opener, Sabrina Carpenter, as the musical guest.
While Swift’s love life has provided fodder for numerous sketches on the late-night comedy show, it remains to be seen whether the global pop star of the moment will be mentioned on the episode.
The 34-year-old songstress took a walk down memory lane with her 11th studio album, The Tortured Poets Department, which was released on April 19 to much fanfare. Swifties quickly took several Easter eggs into evidence, speculating that a number of her latest songs were written about her failed relationships with Joe Alwyn and Matty Healy. Fans also surmised that two new love songs may have been written about her current relationship with Kansas City Chiefs star Travis Kelce.
Gyllenhaal previously found himself under intense scrutiny following the release of Red (Taylor’s Version) in 2021. The 43-year-old Road House actor is rumored to be the subject of Swift’s fan-favorite song, “All Too Well,” and its deeply detailed accompanying 10-minute version.
While Swift tends to keep her cards close to her chest when it comes to her real-life muses, the 14-time GRAMMY winner has long been known to use her songwriting talents as a way to channel personal struggles and triumphs into record-breaking album sales and awards acclaim.
Now, ET is taking a Lover look back at Swift’s most famous relationships and some of the men who are rumored to be attached to her biggest hits.
2008: Joe Jonas
Joe Jonas and Swift dated for just a few months in the summer of 2008, but their relationship has since lived in infamy after Swift said during an appearance on The Ellen DeGeneres Show that her ex had ended things via a 25-second phone call. Speak Now‘s “Last Kiss” and “Better Than Revenge” (2010) and Fearless‘ “Forever and Always” (2008) are both said to be about the breakup. Fans also speculate that Red‘s “Holy Ground” (2012) is a reference to her 2008 performance with the Jonas Brothers.
Swift later told DeGeneres that she regretted her original remarks about Jonas’ breakup with her. “That was too much, that was too much,” she said during a 2019 appearance on the show. “I was 18…we laugh about it now, but that was mouthy, yeah, some teenage stuff there.” Jonas later said he appreciated the apology, too. “It did feel nice,” he said several weeks later on ITV’s Lorraine show. “It’s something that I was probably feeling pretty bad about when I was younger, but, at the end of the day, I’ve moved on. I’m sure Taylor’s moved on. It feels nice. We’re all friends. It’s all good. We were so young.”
2009: Taylor Lautner
Swift dated Twilight star Taylor Lautner from October to December 2009, around the same time that they co-starred as high school sweethearts in Garry Marshall’s romantic comedy, Valentine’s Day. Swift’s much-beloved song, “Back to December,” from 2010’s Speak Now, is allegedly an apology to Lautner revolving around the night she broke up with him.
Swift and Lautner have since become good friends. Following her release of Speak Now (Taylor’s Version), Lautner starred alongside Joey King and Presley Cash in a music video for Swift’s vault track, “I Can See You.” Swift debuted the video during a performance at the Eras tour in Kansas City, where Lautner, King and Cash joined the singer onstage following its premiere.
“Taylor, I respect you so much,” Lautner told Swift after backflipping onto the stage. “Not just for the singer you are, the songwriter, the performer, but for the human you are. You are gracious, humble, kind and I am honored to know you.”
2009: Lucas Till
Lucas Till briefly dated Swift after starring as her next-door neighbor in the 2009 music video for “You Belong With Me.” Till also starred as Travis Brody in 2009’s Hannah Montana: The Movie. His relationship with Swift only lasted a few months because according to Till, the pair was better off as friends.
“We dated for a little bit. But there was no friction because we were too nice,” he told MTV that same year. “We just really both liked each other… [but] most relationships work out ’cause you get along and then you don’t, and then you make up and it’s passionate, and with us, I really just liked her as a friend. That’s the only reason that didn’t work out.”
2009-10: John Mayer
John Mayer and Swift were romantically linked from late 2009 to early 2010, when Swift was 19 and Mayer was 32. Swift’s 2010 Speak Now track, “Dear John,” is the singer’s most infamous alleged reference to the much-discussed relationship. A trio of especially cutting lines read, “Don’t you think I was too young to be messed with? The girl in the dress cried the whole way home. I should’ve known.”
Swifties are often fervent in their dislike of Mayer, both for the couple’s drastic age difference and for theories about Mayer’s alleged treatment of Swift based on her lyrics. Mayer later complained to Rolling Stone about “Dear John,” saying the track made him “feel terrible,” explaining, “I didn’t deserve it. I’m pretty good at taking accountability now, and I never did anything to deserve that. It was a really lousy thing for her to do.”
Swift addressed her fans’ distaste for Mayer at an Eras tour performance in 2023, when she asked Swifties to practice kindness ahead of her re-recording of Speak Now.
“I’m 33 years old, I don’t care about anything that happened to me when I was 19 except the songs I wrote,” she told the crowd. “So what I’m trying to tell you is that I’m not putting this album out so that you could go and should feel the need to defend me on the internet against someone you think I might have written the song about 14 billion years ago.”
2010-11: Jake Gyllenhaal
Swift and Jake Gyllenhaal were in an on-again/off-again relationship from October 2010 into early 2011, when Swift was 20 and Gyllenhaal was 29. Fans believe several of the songs on Swift’s 2012 album, Red, are about her relationship with Gyllenhaal, including lead single “We Are Never Getting Back Together” and the power ballad, “All Too Well.”
When Swift released Red (Taylor’s Version) in 2021, she also recorded her original 10-minute draft of “All Too Well,” this time titled “All Too Well (10 Minute Version) (Taylor’s Version) (From The Vault),” which further details an exploitative relationship between a young woman and an older man who many fans still believe to be Gyllenhaal. The new version of the song quickly landed at No. 1 on the Billboard Hot 100, her eighth song at the time to reach such status. Swift also subsequently released a short film featuring the track starring Dylan O’Brien and Sadie Sink, and later that week performed the 10-minute number on Saturday Night Live.
Gyllenhaal turned off his Instagram comments around the time of Red (Taylor’s Version)‘s release, leading many to assume he was facing an onslaught of personal attacks in response to the album. He later told Esquire that he did not resent Swift for her release of the extended “All Too Well,” alleging the song “has nothing to do with me.”
“It’s about her relationship with her fans. It is her expression. Artists tap into personal experiences for inspiration, and I don’t begrudge anyone that,” he said.
2012: Conor Kennedy
Swift dated Conor Kennedy, grandson of Robert F. Kennedy, during the summer of 2012. At the time, Swift’s love of the Kennedy family was well-documented, including one 2011 Rolling Stone interview in which the singer said she had just finished “a 900-page book called The Kennedy Women, which dates back to the lineage of the first Kennedys coming from Ireland in the 1800s.”
Swift met Kennedy through her connections with his aunt, Rory Kennedy. Many fans believe her song, “Begin Again,” from 2012’s Red, is about the start of Swift’s relationship with Kennedy following her breakup from Gyllenhaal.
2012-13: Harry Styles
Pop star and former One Direction singer Harry Styles dated Swift from October 2012 to January 2013. Before they made their relationship official, some fans believe Swift wrote her Red track, “I Knew You Were Trouble,” about a fling with Styles earlier in 2012. Following their split, many believe tracks “Out of the Woods,” “Style,” “All You Had to Do Was Stay,” “I Wish You Would,” “How You Get the Girl,” “This Love,” “I Know Places,” “Clean” and “Wonderland” — all from Swift’s 2014 album, 1989, are about Styles. Off her 2022 album, Midnights, many also posit that the songs “Maroon” and “Question…” are about him as well.
In 2020, Styles told Howard Stern he was ultimately happy to be the subject of any of Swift’s songwriting. “I think about what it means to me to write a song about somebody else and for somebody else to do that, it’s, like, flattering. Even if the song isn’t that flattering, you still spent time on it and ultimately, using Taylor as an example, she’s a great songwriter. So at least they’re good songs,” he said.
2015-16: Calvin Harris
Swift and Scottish DJ Calvin Harris, real name Adam Wiles, dated for 15 months between 2015 and 2016, eventually breaking things off in March 2016.
By June of that year, Swift had begun dating British actor Tom Hiddleston, and she Swift and Harris had wiped all record of their relationship from their respective social media accounts.
In July, Swift’s rep told People that the singer had written Harris’ song, “This Is What You Come For” featuring Rihanna, under the pseudonym Nils Sjoberg. The revelation came after Harris said in an interview he couldn’t see collaborating with his then-girlfriend.
“You know, we haven’t even spoken about it. I can’t see it happening, though,” Harris said while promoting the song, seemingly contradicting his work with Swift on the track. Reports later surfaced that Swift had been hurt by his comments, and that the disagreement led to the end of their relationship.
Soon after the news broke, Harris commented about the situation on Twitter, where he initially praised his ex for her music skills before then taking a turn for the negative. “And she sings on a little bit of it too. Amazing lyric writer and she smashed it as usual,” he wrote. “I wrote the music, produced the song, arranged it and cut the vocals though. And initially she wanted it kept secret, hence the pseudonym.”
Harris later told British GQ, “It’s very difficult when something I consider so personal plays out very publicly. The aftermath of the relationship was way more heavily publicized than the relationship itself. When we were together, we were very careful for it not to be a media circus. She respected my feelings in that sense.”
Many fans believe Swift’s 2017 track, “Dancing With Our Hands Tied,” from her Reputation album, and 2019’s “I Forgot That You Existed,” from Lover, are both about Harris.
2016: Tom Hiddleston
Swift briefly dated British actor Tom Hiddleston during the summer of 2016, after the two were first spotted together at the Met Gala a few days before Swift’s breakup with Harris. Later, Swift and Hiddleston were seen kissing on a beach in June 2016, and Hiddleston wore his now-iconic “I ♥ T.S.” tank top at Swift’s Fourth of July beach bash.
By September, however, ET had confirmed the couple’s breakup. “It was an amicable split,” the source said. Though the relationship was short-lived, many allege that Swift’s hit song, “Getaway Car,” off 2017’s Reputation, is about the couple’s whirlwind romance.
2016-23: Joe Alwyn
Swift’s relationship with British actor Joe Alwyn was perhaps the one she kept the most private, with very little PDA and no Instagram or red carpet appearances. Though it’s unclear when the couple started dating, Swift insinuated in a since-deleted 2022 Instagram post that the couple had been together for six years.
Fans believe much of Swift’s recent discography was inspired by her relationship with Alwyn, including tracks from Reputation (2017), Lover (2019), Folklore (2020), Evermore (2020) and Midnights (2022). Alwyn also boasts an impressive number of co-writing credits, under the pseudonym William Bowery, on albums Folklore, Evermore and Midnights.
On April 8, 2023, shortly after the launch of Swift’s Eras Tour, ET confirmed that the two had ended their relationship. ET also learned that the split was amicable and “not dramatic.”
“The relationship had just run its course. It’s why [Alwyn] hasn’t been spotted at any shows,” the source said.
2023: Matty Healy
The 1975 singer Matty Healy was first linked to Swift when he was spotted at the Nashville stop of her Eras Tour in May 2023, one month after news of her breakup from Alwyn first broke. The duo, who have been longtime friends, was later photographed together as well.
“Taylor and Matty like each other,” a source told ET shortly thereafter. “Taylor has a crush on Matty and they are having a good time hanging out. Matty also thinks Taylor is awesome and incredibly talented, too. They dated briefly in the past.”
By June, though, the romance had ended. “Taylor and Matty broke up,” a source told ET. “They are both extremely busy and realized they’re not really compatible with each other. Taylor’s friends want what’s best for her and aren’t shocked that their relationship fizzled out since she recently got out of a long-term relationship.”
2023: Travis Kelce
In July 2023, Kansas City Chief tight end Travis Kelce revealed on his and his brother Jason’s podcast that he was unsuccessful when he attempted to give Swift a friendship bracelet after the Eras Tour concert at Arrowhead Stadium in Kansas City. Also on the podcast, he admitted that his bracelet had his phone number on it.
Though romance rumors simmered among fans after Kelce’s reveal, it wasn’t until late September that fans first spotted Swift inside Arrowhead Stadium as the Chiefs took on the Chicago Bears. During the game, she rocked a Chiefs jacket while seated next to Kelce’s mom, Donna Kelce, in the NFL player’s suite.
Swift and Kelce were seen together for the first time later that night, leaving the stadium in Travis’ convertible and attending a team party nearby.
After that, Swift attended numerous games in support of her boyfriend and was even photographed with Kelce in New York City on the same day they both made appearances on Saturday Night Live.
The two have gone on to become one of the biggest power couples in the world, with Kelce winning his third Super Bowl and Swift earning her historic fourth Record of the Year at the GRAMMYs.
“Travis has never felt more supported by a significant other ever. This is just the beginning for them as a couple and many milestones are coming their way. Taylor and Travis make time for each other because they want to. They both take so much pride in the importance of family and love bringing their families and close-knit circles together. They are genuine, honest, loving and forthright with each other across the board. They both continually encourage one another to be the best that they can be,” a source told ET in February ahead of the Super Bowl and after the GRAMMYs.
Another source added, “Travis is in love with Taylor and he’s never been happier. Taylor’s feelings are mutual and she is so happy and feels comfortable with Travis. She loves that she can be open with their relationship, live her life, and enjoy this special time together.”
In the months following the GRAMMYs and the Super Bowl, the pair have been more visible with their relationship than ever, whether that means enjoying a casual date night in Los Angeles at a prime sushi spot or taking their love to Coachella to partake in the famed desert festivities.
The couple enjoyed a little R&R on a vacation in the Bahamas at the end of March, where they were photographed holding hands and packing on the PDA while soaking up the sun.
In early April, just days before Swift dropped her highly-anticipated 11th studio album, The Tortured Poets Department, the couple was spotted in videos and photos posted online making out at Coachella, where her friends, Jack Antonoff and Lana Del Rey, were both performing.
A source close to the pair told ET, “Taylor and Travis were so excited to go to Coachella together. They wanted to be there to support their friends and just have fun. They had the best time at the festival and were in their own world even though so many people were around them.”
The source added, “They are very in love and in sync in so many aspects of their lives, and it’s very sweet to see.”
Around the same time, Kelce and his brother, former Philadelphia Eagles player Jason Kelce, invited Lil Dicky (a.k.a. Dave Burd) on their New Heights podcast, where the Chiefs tight end shared how his relationship with Swift began.
Kelce joked, “I don’t know how I did it because she was not into sports. So I don’t know how the f**k I did it.”
Swift has shown her enduring support of Kelce’s NFL career by attending a number of his games, while Kelce has returned the favor by jetting around the world to attend her Eras performances.
Most recently, Kelce was spotted dancing in the audience during one of Swift’s concerts in Paris as she sang “So High School” and “The Alchemy,” both of which fans believe were written about him.
A source told ET, “Taylor’s 87th show had significance not only for the reference to Travis’ football jersey number, but because of the many Easter eggs hidden in the show about Travis. This was also the first time Travis was able to hear songs live that are rumored to be about him, and he was thrilled.”
On Friday, a source said that Swift and Kelce’s loved ones are betting on a quick engagement.
The source told ET, “Taylor and Travis are doing amazing, and their loved ones see an engagement coming sooner than later. They make a great match and there’s no question about that.”
For more on Kelce and Swift’s whirlwind romance, check out the links below.
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