Joe Jonas
These two cuties seem to have come full circle in the years since they dated. They became a ‘thing’ in July 2008 and ended things in October that year, allegedly via a 27-second phone call. Their brief romance inspired a lot of Taylor’s early work, with songs like Last Kiss on her Speak Now album and Forever and Always on Fearless, a last minute addition before the album’s release in November 2008.
Now, it appears Taylor is friends with Joe and his wife, Game of Thrones actress Sophie Turner. They were seen attending the after party for Taylor’s Saturday Night Live performance just this weekend. Also, in her folklore track Invisible String, she sings “cold was the steel of my axe to grind for the boys who broke my heart/now I send their babies’ presents”. Joe and Sophie have a one-year-old, Willa, and we can’t help but wonder if this is the baby Taylor is referring to.
Lucas Till
Although just a flash in the pan, Lucas has discussed his brief fling with Taylor, meaning it’s a necessary inclusion. The pair met on the set of the video for Taylor’s song You Belong With Me and went on to hang out as more than mates.
“We dated for a little bit. But there was no friction because we were too nice. We just really both liked each other…” Lucas told MTV.
“[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.”
Taylor Lautner
The Taylor/Taylor time marks a golden era in Taylor’s dating history, because for a few months, these two had the relationship we all wanted to be in. The Twilight actor with biceps for days paired with Taylor at the height of her Fearless fame? It was a teenage dream we all wanted to be living.
The two were short-lived, but birthed the tune Back to December, from which fans were able to glean that the breakup was Taylor (Swift)’s choice, and that Taylor (Lautner) perhaps was a little bruised by it.
John Mayer
Turns out Twilight Taylor’s feathers were not the only ones ruffled by the Speak Now era. Taylor wrote Dear John about the end of her tryst with John Mayer, which honestly gave off a few weird vibes. The line 'Don’t you think nineteen's too young to be played by your dark twisted games?' raised a few eyebrows, especially given that John was 13 years older than Taylor.
John was, unsurprisingly, not pleased with the lyrics.
“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 said to Rolling Stone.
Jake Gyllenhaal
To any person who’s ever experienced a “situationship”, this one goes out to you. Taylor dated angel-faced actor Jake Gyllenhaal only for three months, yet it inspired some of her greatest work to date on Red, which we let hurt us all over again just this past weekend.
Unlike John Mayer, the subject of Red (Jake) took the release of the album really well.
“‘I just listened to the album, and that was a really bittersweet experience for me. It was like going through a photo album,’” Taylor quoted the man in question to New York Magazine.
“That was nice. Nicer than, like, the ranting, crazy emails I got from this one dude,” she added.
“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.”
We can perhaps then confirm, that the love affair maimed Jake too.
Conor Kennedy
Taylor followed up her fling with Jake by dating Conor Kennedy. They spent a number of summer days together, looking like a version of the American dream, before splitting amicably a few months later.
It’s widely believed that Begin Again, the final track on the original version of Red, was about Taylor meeting and getting to know Conor. It included some pretty heartbreaking lines about the perspective a new flame can bring. ‘I think it’s strange how you think I’m funny, ‘cause he never did’ was one that stood out in particular, and we still hold a grudge against any man who told Taylor she wasn’t funny. Rude.
Harry Styles
Taylor’s next brief relationship also had a profound impact on us … as we’re sure it did on Taylor, too. Taylor was first spotted wearing Harry Styles’ silver airplane necklace in November 2012, and the pair were seen out together shortly after – going on to date until approximately January 2013.
The 1989 tracks Out of the Woods and Style are allegedly about Harry. Taylor wore the airplane necklace in the video for Out of the Woods, and the song referenced a car accident the pair were in together. And if the line ‘you’ve got that long hair, slicked back, white T-shirt’ wasn’t about Harry, we have no clue who she might have been referencing.
Things got weird post-breakup at the 2013 Grammys, when Taylor allegedly dissed Harry by using a British accent for the male voice part during her performance of We Are Never Ever Getting Back Together. It was the Swifties vs the Directioners and Twitter was not a fun place to be.
In the year's since they've become friendly, with Harry and Taylor spotted chatting at the 2021 Grammys - where they both walked away with major awards.
Calvin Harris
Taylor dated Calvin Harris for about 14 months in 2015 and 2016. The pair were introduced by a mutual friend, Ellie Goulding, and enjoyed quite a low-key relationship for the most part. However, it was reportedly broken off by Calvin Harris in May 2016, and then things got messy.
He might have-kind of accused her of cheating in some of his lyrics, while she made direct reference to him in her famously high-key music video for Look What You Made Me Do, the first single off Reputation.
In the video, a grave was shown with the name ‘Nils Sjöberg’, which was the pseudonym Taylor was credited under on Calvin’s 2016 single ‘This is What You Came For’. Drama? We think so.
Tom Hiddleston
We love Taylor, and we love Tom, but we’re not sure how we feel about their time together. The pictures of them kissing atop a rocky outcrop that went out in The Sun seemed somewhat staged, and if it wasn’t a PR relationship, we’re concerned as to why Tom was spotted wearing a shirt with the words ‘I HEART TS’ emblazoned across the front? Maybe he was just really, really intense? Somehow, we doubt it, but still, a memorable time in Taylor’s dating history.
Joe Alwyn
While it hasn’t been confirmed, we and many other fans have reason to believe that Taylor met her boyfriend of four-fiveish years, Joe Alwyn, at the 2016 Met Gala, where she was also captured dancing with Tom Hiddleston. Oops.
Reports emerged that they were dating in mid-2017, and then in October of that year, Taylor allegedly confirmed to fans at a secret listening session for Reputation that the song Gorgeous was about Joe Alwyn.
The pair, who are still notoriously private, were spotted together throughout the years, but gone were the days of cheesy pap photos and Instagram tributes. In her 2020 documentary, Miss Americana, Taylor admitted that while her life was spiralling from the fall out from her drama with Kim Kardashian and Kanye West, “I also was falling in love with someone who had a wonderfully normal, balanced life.”
“We decided together we wanted our relationship to be private,” she said, and it has remained that way ever since, with the occasional tidbit bubbling to the surface ever since.
It seems that after many years, Taylor has found the great love she sings of in songs like Lover, invisible string, Paper Rings, London Boy, etc. And we’re very happy for her to keep it to herself, so long as she keeps making the music we love so much.
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