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Taylor Swift Dating History: A List Of The Men In The “Me” Singer’s Life And The Songs Based On Them

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Taylor Swift

Taylor Swift is known to have drawn inspiration from her real life experiences for her songs. Below are some of her most notable relationships and her songs inspired by those relationships.

Joe Jonas

Taylor dated Joe Jonas in the summer of 2008, but things were over by fall. Still, the relationship remains infamous because of its cruel and cold end. In a November 2008 appearance on Ellen, Taylor explained,

“When I find that person that is right for me he’ll be wonderful. And when I look at that person, I’m not even gonna be able to remember the boy who broke up with me over the phone in 25 seconds when I was 18.”

Swift went on to write three songs about Jonas: “Last Kiss”, “Better Than Revenge,” and “Forever and Always”.

But a lot can change in a decade. In May 2019, Taylor returned to Ellen. During a segment called “Burning Questions,” DeGeneres asked her guest to name the most rebellious thing she did as a teenager.

“Probably when I put Joe Jonas on blast on your show. That was too much… We laugh about it now but that was some mouthy—yeah, just some teenage stuff there.”

Lucas Till

In March 2009, Taylor briefly dated actor Lucas Till. The two met on the set of Hannah Montana: The Movie, but the flame flickered out after just one month. Till told MTV News in 2019–

“We dated for a little bit. But, there was no friction because we were too nice. 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.”

However, Till managed to nab a spot in the music video for her song, “You Belong With Me.”

Taylor Lautner

August 2009 marked the birth of Taylor Squared—a five month-long period where Swift was linked to Twilight star, Taylor Lautner. The two met on the set of the 2010 rom-com Valentine’s Day, in which they play high school sweethearts.

Their attempt at a real-life romance didn’t last very long, but sources say that neither shed tears over it. And yet, Swift reflected on their time together in “Back to December,” off of her 2010 album Speak Now.

John Mayer

From December 2009 to February 2010, Taylor dated fellow singer-songwriter John Mayer. The two forged a bond over music, with Taylor collaborating on “Half of My Heart” for Mayer’s 2009 album Battle Studies.

But perhaps their age difference—Mayer is 15 years her senior—is something they couldn’t overcome. In “Dear John”, she sang about it.

Jake Gyllenhaal

In October 2010, actor Jake Gyllenhaal entered Taylor’s life. Things intensified at warp speed, with Gyllenhaal reportedly spending $160,000 to fly her on a private jet for a date in London. However, the romance lasted all of three months.

In a tense 2017 interview with The Guardian, the actor repeatedly shuts down questions regarding Swift. “I would love to not talk about my personal life,” he said. Meanwhile, Swift predictably worked through her feelings by writing 2012’s “Red”. She said in a Rolling Stone podcast–

“I look back on this as my only true break up album. Every other album has flickers of different things–this was an album that I wrote specifically about a pure, absolute, to the core heartbreak.”

In “All Too Well” Swift sings, “Left my scarf there at your sister’s house / And you still got it in your drawer even now.” Fans are convinced this is a reference to a paparazzi photo where Taylor and Gyllenhaal are seen walking arm in arm while she dons a striped scarf. (When asked if it’s still at her place, actress Maggie Gyllenhaal said, “It’s totally possible. I don’t know.”)

“We Are Never Ever Getting Back Together,” “State of Grace,” and “The Moment I Knew” are also rumored to be about Gyllenhaal.

Conor Kennedy

From July through October 2012, Taylor was romanced by Conor Kennedy, grandson of Robert F. Kennedy. It all started when word got out that “Starlight,” off of Red, was inspired by the relationship between Bobby and Ethel Kennedy. Rory, Ethel’s daughter, reached out to Taylor and gave her entry into the famed family’s world.

Unfortunately, rumor has it some of Kennedy’s blue blood relatives weren’t too keen on the musician. In August, when Taylor showed up at the wedding of one of Conor’s relatives, the mother of the bride asked her to leave. Vicki Kennedy told the Boston Herald–

“I personally went up to Ms. Swift, whose entrance distracted the entire event, politely introduced myself to her, and asked her as nicely as I could to leave. It was like talking to a ghost. She seemed to look right past me.”

Some believe a line in the song “Begin Again” (“I think it’s strange that you think I’m funny ’cause he never did”) is a reference to Conor.

Harry Styles

In December 2012, following months of rumors that they were an item, Taylor stepped out with One Direction’s Harry Styles. Everything about the pair screamed of young love, from using pal Justin Bieber to spread the word of Taylor’s crush on Styles to the matching necklaces they wore.

But just after the new year, while on holiday in the British Virgin Islands, the couple reportedly had a blowout fight and Taylor made a solo journey back to Nashville. Taylor drew on the experience for songs on “1989”. She sang about it in “All You Had to Do Was Stay”. Styles handled it with maturity, telling Rolling Stone,

“I’m lucky if everything [we went through] helped create those songs. That’s what hits your heart.”

Calvin Harris

From March 2015 to June 2016, Taylor dated superstar DJ Calvin Harris. The two were introduced by Ellie Goulding at the 2015 Elle Style Awards and were attached at the hip from that moment on.

But things went sour shortly after their one year anniversary. Things got worse after their actual breakup, with Taylor’s rep revealing to People that Swift had ghostwritten Harris’ hit “This Is What You Came For,” featuring Rihanna.

Taylor Swift Calvin Harris

Harris, triggered by Taylor’s new relationship with Tom Hiddleston, went on a since-deleted Tweet rampage. He wrote–

“I figure if you’re happy in your new relationship you should focus on that instead of trying to tear your ex bf down for something to do.”

Theories are abundant when it comes to Taylor’s 2019 album Lover. “I Forgot That You Existed” and “I Did Something Bad” are allegedly about Harris, if not—believe it or not—Kanye West. Others believe “Dancing With Our Hands Tied,” in which Swift sings about an invisible locket, is about the end of her time with Harris (who once gifted her with a locket).

Tom Hiddleston

Between June and September 2016, Taylor was linked with Avengers star Tom Hiddleston. That’s right—Swift fell into his arms only weeks after her split with Harris. The two hit off at the Met Gala that year, but after only a few months, things didn’t work out. Swift addressed Hiddleston in “Getaway Car,” suggesting that she used him as an excuse to leave Harris (ouch).

Taylor Swift Tom Hiddleston

Joe Alwyn

Rumors that Taylor was dating her current boyfriend, English actor Joe Alwyn, began around May 2017.

In October, at a secret listening session for her album Reputation, Swift told a crowd of 300 attendees that the track “Gorgeous” was about Alwyn. Almost a year later, the couple was still managing to keep a low profile. Alwyn told British Vogue,

“I’m aware people want to know about that side of things…but I really prefer to talk about work.”

Taylor Swift Joe Alwyn

This November, Taylor finally revealed some thoughts about the relationship. In an interview with Paul McCartney for Rolling Stone, Swift praises the music icon for successfully separating fame from his personal life. And shares her struggle to do the same.

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