Taylor Swift Dating History – Taylor Swift Ex-Boyfriend History


Taylor Swift gets a lot of extremely unfair sh*t for dating celebrities and then writing songs about them. But without Taylor’s openness and honesty about her romantic life and exes, we wouldn’t have some of her best lyrical work—including her collaboration with a certain someone who goes by the name William Bowery or an entire rerelease of Red (come for the extended track list, stay for the Jake Gyllenhaal shade!). And on that note, here’s a look back at everyone who has been lucky enough to date Tay (lol, hi, Tom Hiddleston, nice to see you again).

JOE JONAS: JULY 2008 TO OCTOBER 2008

Joe and Taylor barely dated, yet their breakup was somehow the most dramatic thing ever. Probably because he rudely ended things over the phone—which Taylor confirmed during a November 2008 appearance on Ellen, saying:

“When I find that person who 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.”

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Memorable Moment: Taylor Swift on Joe Jonas

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Taylor later released a Joe-inspired song called “Forever and Always,” which includes the pretty pointed lyrics, “Was I out of line? / Did I say something way too honest, made you run and hide / Like a scared little boy.” Yikes!

And while Taylor has since apologized for putting Joe on blast, just a fun reminder that in 2009, she mentioned their breakup in her Saturday Night Live opening monologue:

“You might think I’d bring up Joe, that guy who broke up with me on the phone. But I’m not going to mention him in my monologue. Hey, Joe! I’m doing real well and I’m hosting SNL—but I’m not going to write about that in my monologue.”

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Taylor Swift Monologue Song – SNL

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What is having chill, even?

LUCAS TILL: MARCH 2009 TO APRIL 2009

‘Kay, so Lucas played the guy in Taylor’s “You Belong With Me” video, and apparently they dated for a minute. At least, according to Lucas, who told MTV:

“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.”

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Taylor Swift – You Belong With Me

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TAYLOR LAUTNER: FALL 2009

Taylor and Taylor (help) were an item while filming Valentine’s Day, where they shared several iconic scenes together:

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Valentine’s Day (2010) – Young Love Scene (5/9) | Movieclips

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She allegedly wrote “Back to December” about him, and when asked what he thought of the song in 2016, Twilight Taylor mused, “That’s what she does.”

Wow, the implied rudeness is enough for me to join Team Edward FOR LIFE.

JOHN MAYER: DECEMBER 2009 TO FEBRUARY 2010

Who can forget this relationship? NO ONE, THAT’S WHO. Taylor and John Mayer dated for just a few months, and their breakup was a massive mess thanks to John’s terrible reaction to Taylor writing “Dear John” about him.

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John complained to Rolling Stone in a highly whiny interview, saying, “I never got an email. I never got a phone call. I was really caught off guard, and it really humiliated me at a time when I’d already been dressed down. I mean, how would you feel if at the lowest you’ve ever been, someone kicked you even lower?”

He added, “I will say as a songwriter that I think it’s kind of cheap songwriting. I know she’s the biggest thing in the world, and I’m not trying to sink anybody’s ship, but I think it’s abusing your talent to rub your hands together and go, ‘Wait till he gets a load of this!’ That’s bullshit.”

@ John, you need to calm down.

JAKE GYLLENHAAL: OCTOBER 2010 TO JANUARY 2011

Us Weekly broke the news of these two dating in a December 2010 cover story, blessing the universe with these photos:

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Us Weekly

Fast-forward to January and the magazine reported that Jake broke up with Taylor completely randomly. “It was a 180-degree turn and so out of the blue,” a source said at the time. “Jake just told her it wasn’t working out.…Taylor is really upset and hurt. She doesn’t know what she did for him to put a stop to it. She feels really burned by him.”

A bunch of songs on Red were allegedly inspired by Jake and he was completely cool with them. Taylor didn’t exactly name names, but she *did* tell New York Magazine that the man in question told her…

“‘I just listened to the album, and that was a really bittersweet experience for me. It was like going through a photo album.’ That was nice. Nicer than, like, the ranting, crazy emails I got from this one dude. It’s a lot more mature way of looking at 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. So what are you going to do? Did you not Wikipedia me before you called me up?”

CONNOR KENNEDY: JULY 2012 TO OCTOBER 2012

Good ol’ Us Weekly also broke the news of Connor and Taylor’s relationship after they were photographed together in Hyannisport, Massachusetts, and an onlooker revealed that “Connor put his arm around Taylor and they kissed behind the boat shed.”

The good news is the split was “totally amicable and down to the distance between them,” according to E!, but I’m personally still bummed Taylor didn’t become a casual Kennedy.

HARRY STYLES: NOVEMBER 2012 TO JANUARY 2013

QQ: How much coffee have you had? Because the Harry Styles section of this timeline is best described as EXHAUSTING despite spanning just three months. Rumors about Haylor started flying around after Tay was spotted wearing Harry’s silver airplane necklace—which she also wore in the video for her Harry Styles breakup song “Out of the Woods.” See?

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In December, these two “went public” when they were photographed strolling around the Central Park Zoo—but after just a few months of dating and one vacation where Taylor was seen sitting alone on a boat, Haylor broke up. Things were pretty awkward henceforth, especially when Taylor dissed Harry during her 2013 Grammys performance by using an English accent.

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Taylor Swift mocking/dissing Harry Styles during Grammy performance

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CALVIN HARRIS: FEBRUARY 2015 TO MAY 2016

Taylor and Calvin met at the Elle Style Awards in February, and good news: There is photo evidence.

A month later, they were spotted in matching outfits at a Whole Foods in Nashville, the setting of all love stories.

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Tayvin went public at the 2015 Billboard Music Awards in May, and they even kissed for the cameras.

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The pair celebrated their one-year anniversary on March 6, 2017…

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But then two months later, People reported that Calvin broke things off. The breakup was deeply messy, with Calvin low-key accusing Taylor of cheating in some song lyrics.

TOM HIDDLESTON: MAY 2016 TO SEPTEMBER 2016

Remember when Taylor was dating the poor lost soul known as Tom Hiddleston? No? Well, here’s a reminder. This unlikely relationship started at the Met Gala, where Taylor and Tom were seen dancing the night away:

THEN June rolled around and The Sun published pictures of them kissing atop a rocky outcrop in Rhode Island. The internet had questions! Questions like, Were these pictures staged, y/n?

Things went full steam ahead after the photos went viral. Tom met Taylor’s parents in Nashville, they were seen dancing at a Selena Gomez concert, and Tom was spotted wearing an “I HEART TS” tank top while frolicking in the ocean with Taylor and a bunch of supermodels.

Alas, things went south for the couple in September 2016, with sources saying Taylor was worried Tom wasn’t with her for the right reasons.

JOE ALWYN: MAY 2017 TO NOW

Taylor and Joe met on The! First! Monday! In! May! which is the fancy way of saying at the Met Gala. To be honest, this hasn’t *actually* been confirmed by anyone, but fans think Taylor’s song “Dress” implies they had a moment at the event based on these lyrics: “Flashback to when you met me / Your buzz cut / And my hair bleached.”

Reminder: This is what Tay looked like on that fated night (yeah, same Met Gala as that scarring Instagram video above, and apparently Joe, not pictured, had a buzz cut):

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An entire year later, British tabloid The Sun broke the news that Taylor and Joe were dating, that she’d been staying in London in disguise, and that she and Joe were “the real deal.” Then in December 2017, Jaylor were seen publicly swaying at an Ed Sheeran concert:

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And in March 2018, she wore his initials around her neck:

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Flash-forward to September, and Taylor was spotted sneaking into the premiere of Joe’s new movie The Favourite—and yes, paps were there to snap pics:

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THEN, in February 2019, they were spotted getting super cozy at the BAFTAs. Things have been going strong ever since, with Joe (er, William Bowery) collaborating with Taylor on Folklore and the singer addressing her now six-year romance with the actor on her latest album, Midnights.

You can get a full rundown of their relationship this way, bye!

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