Taylor Swift’s Dating Journey Through Time: A Comprehensive Timeline

Published 01/21/2024, 9:16 AM EST

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Lately, Taylor Swift has been on a wild rollercoaster of success. First, blowing minds with her Eras Tour and then shattering records with a concert film that practically set the screen on fire. Here is the curveball: she dipped her toes into the sports scene, scoring a touchdown of her own by cozying up to NFL tight end Travis Kelce. Swift stole the show in the stands, not just with her usual chart-toppers, but with A-list friends in tow and dances that could rival any Broadway performance. Most of Swift’s hits are straight from the pages of her own life. 

Let us rewind the tape and dive into Swift’s romantic escapades, starting from the early-aughts flirtation with Joe Jonas to her latest touchdown dance with a Kansas City Chiefs player. The love life exposé below is like a nostalgic road trip for Swifties, where each pit stop is a reminder of those heart-fluttering moments that probably sparked some of our favorite tunes.

Joe Jonas

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Since the dawn of her musical journey, Swift’s fans played detective, digging into the cryptic tales of characters like Drew and Cory in her debut. However, the inaugural chapter in Swift’s public romance unfolded with Joe Jonas in 2008, a fleeting affair that left fans yearning for the inside scoop. Despite the elusive details, the duo called it quits in October 2008. It was just a whisker away from Swift unleashing her second studio album, ‘Fearless.’

In the aftermath, Swift transformed heartache into art, crafting the breakup anthem ‘Forever & Always’. Confirming the song’s muse, Swift cheekily spilled the tea on The Ellen DeGeneres Show. She envisioned a future where she would find a love so grand that memories of the boy who broke up with her over the phone in 25 seconds at 18 would fade away like a distant dream. The melodic saga continued with ‘Mr. Perfectly Fine,’ the lyrics of which echoed the melodies of her time with Jonas.

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Conor Kennedy

Indeed, Conor is a chip off the old Kennedy block, being the son of Robert F. Kennedy Jr. The political scion and Swift dove into a summer fling in 2012, creating ripples of gossip as they were caught canoodling behind the boat shed at Hyannisport, Massachusetts. However, despite the fiery romance, the leaves fell on their love tree by October of the same year.

In an interview with Katie Couric, Swift confessed that she did not know how to navigate a normal relationship, attempting to act and love from an ordinary place while leading a regular life. With a touch of humor, she amusingly added that eventually, she did not really know that much about love.

Harry Styles

The Haylor fling may have been a flash in the pan, but there is nothing like the sizzling gossip that erupts when two music maestros tango. Swift kicked off the rumor mill in November 2012, subtly donning Styles’ iconic paper airplane necklace, a move that set fans’ Sherlock instincts on high alert. The fire was fanned with a December date at the Central Park Zoo.

More so, sparks flew as they locked lips during Dick Clark’s New Year’s Rockin’ Eve with Ryan Seacrest in January. However, the love boat hit choppy waters in the US Virgin Islands that same month, leaving Swift to navigate solo, immortalized in a viral snapshot of her in a lone blue dress on a boat. The Grammy stage became the grand theater for closure in February, as Swift belted out ‘We Are Never Ever Getting Back Together’ with a surprising British accent.

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Calvin Harris

Swift’s encounter with her musical match and eventual sweetheart went down at the ELLE Style Awards in February, courtesy of a matchmaking move by her buddy Ellie Goulding. (Fun fact: Goulding and Harris had teamed up on the track ‘I Need Your Love’ back in 2012.) Fast forward a month, and sparks were flying as Swift and Harris officially hit the dating dance floor. This milestone was celebrated a year later with a sweet anniversary cake shared on Harris’s Instagram.

Their love affair was not shy of a public smooch, with Swift planting one on the DJ at the Billboard Music Awards come May. However, by the same month, Swift and Harris’s romantic melody hit a sour note, coinciding with Swift’s entanglement with two future love interests: Tom Hiddleston and Joe Alwyn.

Tom Hiddleston

In the midst of her Calvin Harris chapter, Swift twirled into the arms of Tom Hiddleston at the Met Gala. The new couple’s dance-off was caught on tape by a fellow reveler. Sparks flew, and the duo embarked on a whirlwind romance in 2016. It was all about a June meeting on a rock outside Swift’s Rhode Island mansion. More so, they shared a kiss fit for a romantic movie. They did not shy away from the spotlight, even earning a spot at Swift’s legendary Fourth of July party.

Adding to the hype, Hiddleston rocked an “I Heart T.S.” tank top. Alas, by September, the love story wrapped up its reel. Despite rumors of it being a PR stunt, Hiddleston set the record straight, declaring in a February 2017 GQ interview that their love was the real deal, painting it as a chapter of fond memories.

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Joe Alwyn

For the Swifties, the love tale between the ‘Midnights’ singer and Joe Alwyn kicked off in 2016. The Met Gala acted as their collision point. Swift’s song ‘Dress’ dropped hints about their first encounter, but it was not until May 2017 that the romance got an official nod. Their dance-floor chemistry hit the spotlight in December, with the duo whirling in each other’s arms at an Ed Sheeran concert.

Steering clear of the paparazzi, Swift and Alwyn kept their love affair on the down low. Sneaky maneuvers included Swift’s covert entrance at the premiere of Alwyn’s film, The Favourite. Their love’s crescendo struck in 2020 at the Golden Globes, where they beamed with affection. Furthermore, Alwyn, under the alias William Bowery, collaborated on Swift’s music, earning him a Grammy for his work on ‘Folklore’. However, in April 2023, the couple called it quits, mutually. It was only then that her iconic hit ‘Lover’ had topped the iTunes charts post the split.

Travis Kelce

In the arena of all things Swift, the story took root with a good ol’ friendship bracelet. NFL player Kelce, making a touchdown attempt at the singer’s Eras Tour in the summer of 2023, had a nifty plan up his sleeve. Armed with a friendship bracelet bearing his digits, he aimed to hand it over to Swift post-show. But the stars did not align, leading him to reveal plans on his New Heights podcast, laying all his cards on the table for Swift to see.

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A mere two months down the calendar, whispers circulated that the duo had kicked off a rendezvous. Soon after, snapshots captured Swift decked out in Kansas City game-day colors, rubbing shoulders with Kelce’s mom in the VIP box. Their adventures traversed Saturday Night Live appearances, cozy hand-holding at various games, and reached a crescendo in Argentina. As of January 2024, insiders spilled the beans, affirming that the couple is riding high on happiness, having a blast, and letting the chips fall where they may.

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Which other flames of Swift do you remember? Let us know in the comments below.

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Riva Khan

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Riva Khan is an entertainment reporter at NetflixJunkie. Given her love for the language and writing, she has honed her narrative skills from a young age. She loves her latest tea in Hollywood and keeps an eye on the news.

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