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Singers, actors, and an NFL star? Taylor Swift’s complete dating history

Singers, actors, and an NFL star? Taylor Swift’s complete dating history

As the queen of break-up anthems, there has been immense (and at times, invasive) intrigue into Taylor Swift’s romantic life. With fans desperately decoding her latest dating updates through lyrics and set list changes, while tabloids pay big bucks for late night dinner date paparazzi pictures.

And boy, has there been a lot of updates these past few months. After her highly publicised and unexpected break-up with actor Joe Alwyn - who many thought Swift had been planning on marrying since the ‘Me!’ music video debuted, in which she’s wearing what appears to be an engagement ring - the pop star seemed to enjoy a single girl summer.

Taylor Swift attends a Kansas City Chiefs game to support rumoured love interest Travis Kelce (USA TODAY Sports via Reuters Con)
Taylor Swift attends a Kansas City Chiefs game to support rumoured love interest Travis Kelce (USA TODAY Sports via Reuters Con)

Most recently the ‘Midnights’ singer was spotted cheering on rumoured beau Travis Kelce. She attended the NFL player’s Kansas City Chiefs games at Arrowhead Stadium over the weekend, where fans held up pun-heavy signs like: ‘He’s Swift to the end zone’ - clearly the pair already have people rooting for them. For any still doubting whether it was simply a coincidence, Swift was also spotted hanging out with Kelce’s mother and filmed hanging out near the locker rooms before the pair were then papped driving around Kansas City in a convertable. It’s giving music video vibes.

There was also the tell-tale admission from Travis’ brother Jason during an appearance on 94 WIP sports radio show: “It’s hard to answer, because I don’t really know what’s happening in Travis’ love life, and I try to, like, keep, you know, his business kind of his business and stay out of that world,” he said, adding: “But having said that, man, I think he’s doing great. I think it’s all 100% true.”

Talk of the pair’s budding romance started in July after the American footballer revealed in an episode of his podcast ‘New Heights’ that he had attended a Taylor Swift concert. “If you’re up on Taylor Swift concerts, there are friendship bracelets and I received a bunch of them being there, but I wanted to give Taylor Swift one with my number on it!” If the photos from over the weekend are anything to go by, it appears he succeeded in his mission.

A source has said about the burgeoning relationship: “She and Travis have hung out twice, and it’s nothing serious. She thinks he is very charming, and they have been texting this last week.” Adding: “He is a little embarrassed at how much attention they are getting, but he has told her he would love to continue seeing her.”

Taylor Swift and Matty Healy leaving their studio session (Claude Yao Sahi @hijoshotit / Shutterstock)
Taylor Swift and Matty Healy leaving their studio session (Claude Yao Sahi @hijoshotit / Shutterstock)

The news comes after a brief but controversial fling with Matty Healy. Having first been linked in 2014 when she was spotted attending his band The 1975’s concert, the two called it quits after Healy revealed fears that he would simply be known as “Taylor Swift’s boyfriend”.

“I was for a very short time immersed in a celebrity world that I found confusing and scary. At that time, I had fears of being ‘somebody’s boyfriend’ … before even being recognized for my music or presence as a person in my own right,” the Grammy nominee explained to Elle in March 2016. At the time he was called out for saying it would feel “emasculating” to date someone as famous as Swift, which he quickly refuted, explaining that “90 percent” of the questions he was asked at the time were “about either [Taylor] as a person or what our ‘interaction’ was like,” which “elicited a lot of self-exploration” about being in the spotlight.

Either way, they two seemingly reconnected over the summer of 2023 - much to the dismay of her fans. Due to Healy’s controversial past and comments made about Swift collaborator Ice Spice, it triggered a viral new hashtag titled #SpeakUpNow, which begged Swift to address the allegations about her and Healy. There was also an open letter that noted fans were “concerned” and were “writing to express our disappointment regarding recent events” regarding Healy.

Fans were finally happy to hear they called it quits in July. A source explained: “Taylor and Matty broke up. They are both extremely busy and realised 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.”

Taylor Swift with ex-boyfriend Joe Alwyn (Blitz Pictures/Shutterstock)
Taylor Swift with ex-boyfriend Joe Alwyn (Blitz Pictures/Shutterstock)

Of course, that long-term relationship was with Alwyn, who she dated for over six years after they met at the 2016 Met Gala. Although they kept their relationship largely out of the spotlight, Swift told the world how happy she was via her Lover album, and in the title track from the 2019 album she sings “my heart’s been borrowed and yours has been blue, all’s well that ends well to end up with you,” leading to more speculation than ever that she’s close to tying the knot with her London boy.

Although no one knows for sure why they broke up, sources claim they called it quits  over “differences in their personalities,” and because the 32-year-old actor “struggled” with Swift’s level of fame, while the 33-year-old pop star “didn’t see them working out in the long run.” However fans speculated that the mass unfollowing of Alwyn from their mutual celeb friends, including Ryan Reynolds, Gigi Hadid and Swift’s childhood best friend Abigail Anderson, suggests there could have been more to it.

Taylor Swift and John Mayerat the Z100's Jingle Ball 2009 (Getty Images)
Taylor Swift and John Mayerat the Z100's Jingle Ball 2009 (Getty Images)

Her relationship with Alwyn might have been under-the-radar, but Swift's past romances were quite public. She had an array high profile ex-boyfriends, who inspired plenty of love (and hate) songs - remember 'Dear John'?

Swift had a few high school beaus, but her first A-list boyfriend was Jonas Brother Joe Jonas, who infamously broke up with her in a 27-second phone call (we wonder what he said). Post Jonas, she was linked to everyone's favourite Twilight werewolf Taylor Lautner.

Later on, Swift also had far more serious relationships, ones worthy of entire albums. She is believed to have commemorated her relationship with Jake Gyllenhaal in the classic breakup scream-along 'All Too Well,' which felt relatable whether or not you've dated Gyllenhaal.

And who could forget the time she almost became a Kennedy? When she was 22 Swift dated then 18-year-old Conor Kennedy from summer 2012 until the autumn. She even bought her own home in Hyannis Port, Massachusetts in an apparent effort to be neighbors with her new boyfriend. While real estate might seem like a high stakes move for a short-lived summer fling, who wouldn’t want to be part of an American dynasty?

And of course, who could overlook her most recent, and most legendary, relationships? Swift dated One Directioner, Harry Styles, reportedly penning 'I Knew You Were Trouble' about him.

Calvin Harris with ex Taylor Swift (Getty)
Calvin Harris with ex Taylor Swift (Getty)

Post-Styles, she also dated DJ Calvin Harris for two years, after meeting him through Ellie Goulding. The couple announced their relationship with an Instagram on top of a swan float. Ultimately, it didn’t last, but it did lead to her making an appearance on Rihanna’s single 'This is What You Came For,' which he produced and Swift wrote.

And then of course, there was the wild summer of #Hiddleswift. Actor Tom Hiddleston notably donned a skin-tight tee proclaiming 'I heart TS' during their July Fourth getaway. Hopefully, Kelce ends up hearting her even more than Hiddleston.