Taylor Swift gets a lot of extremely unfair shit 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 new album The Tortured Poets Department and literally all her re-records (come for the vault tracks, stay for the John Mayer shade!). And, of course, we wouldn’t have the Swiftian magnum opus that is “All Too Well (10 Minute Version) (Taylor’s Version)[From the Vault]” if it weren’t for the twin flame bruise that painted her blue. Moving right along!
On that note, here’s a look back at everyone who has been lucky enough to enter Tay’s romantic realm (lol, hi, Tom Hiddleston, nice to see you again).
jump to:
July 2008—October 2008: Joe Jonas
March 2009—April 2009: Lucas Till
Fall 2009: Taylor Lautner
December 2009—February 2010: John Mayer
October 2010—January 2011: Jake Gyllenhaal
July 2012—October 2012: Connor Kennedy
November 2012—January 2013: Harry Styles
February 2015—May 2016: Calvin Harris
May 2016—September 2016: Tom Hiddleston
May 2017—April 2023: Joe Alwyn
May 2023—June 2023: Matty Healy
July 2023—Right Now: Travis Kelce
July 2008—October 2008: Joe Jonas
Joe and Taylor barely dated, yet their breakup was somehow the most dramatic thing ever. Probably because he ended things over the phone—which Taylor confirmed during a November 2008 appearance on Ellen:
“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.”
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.”
March 2009—April 2009: Lucas Till
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.”
Good! To! Know!!!
Fall 2009: Taylor Lautner
Taylor Squared was an item while filming Valentine’s Day, where they shared several iconic scenes together:
The singer allegedly wrote Speak Now’s “Back to December” about him, and when asked what he thought of the song in 2016, Twilight Taylor mused, “That’s what she does.”
Fast forward to 2023, and T. Swift and “TayTay” are on good terms! Taylor Lautner married another Taylor (I know, it’s hard to keep up ), and the Twilight alum appeared in the Grammy winner’s music video for “I Can See You”:
December 2009—February 2010: John Mayer
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.
Like, John legit complained to Rolling Stone in a 2012 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.
October 2010—January 2011: Jake Gyllenhaal
Us Weekly broke the news of these two dating in a December 2010 cover story, blessing the universe with these photos:
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?”
July 2012—October 2012: Connor Kennedy
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, “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.
November 2012—January 2013: Harry Styles
Q: 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 track “Out of the Woods.” See?
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.
Two Ghosts,” a track off of Harry’s self-titled debut solo album, is also rumored to be about Tay:
Since then, these two have kept things pretty friendly over the years. They reunited at the 2021 Grammys (which set the internet ablaze, btw) and again at the 2023 Grammys.
*** P.S. The October 2023 release of 1989 (Taylor’s Version) blessed us with tons of Harry-coded lyrics, including this one off of the vault track “Is Is Over Now?” Ahem:
February 2015—May 2016: Calvin Harris
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, aka the setting of all love stories.
Tayvin then went public at the 2015 Billboard Music Awards in May, and even kissed for the cameras.
