A Look Back at Taylor Swift’s Ex-Boyfriends in 30 Photos After Her Engagement to Travis Kelce

From young love to a six-year relationship ending in heartbreak and the scathing words of a former boyfriend's mother, take a look back at Taylor Swift's high-profile relationships in 30 photos — ending with her stunning engagement reveal.

America's sweetheart has finally said yes. But before Taylor Swift showed off that enormous oval-cut ring in a lush garden proposal with NFL superstar Travis Kelce, the global icon endured a whirlwind of famous flings and devastating splits.

In an emotional retrospective spanning over a decade of romantic highs and lows, we take a jaw-dropping look back at the men who tried to win the pop star's heart, through 30 unforgettable photos that trace her path from teenage starlet to bride-to-be.

July 2008 – October 2008: Joe Jonas

It all began with Joe Jonas, who dated Swift during the peak of her early fame. The two were inseparable on red carpets, flashing smiles at fans.

Fall 2009: Taylor Lautner

Next came Taylor Lautner, and for a brief, dazzling moment in 2009, Swift seemed to have found her perfect match. Fans adored the pairing, dubbing Lautner her best boyfriend — a sentiment echoed to this day.

In one discussion, people on Reddit debated which of Swift's exes stood out as the most well-regarded, and Lautner's name came up again and again.

One netizen commented, "Obviously Taylor Lautner. Even back in 2010, she admitted through Back To December she was wrong in the relationship and she would give it another try if she could [sic]."

Another chimed in, "probably taylor l. she's admitted multiple times that she was the wrong one in that relationship and she's only said good things about him [...] [sic]." A third added simply, "Taylor Lautner. This is the answer," while another wrote in part, "She's cordial to Taylor."

December 2009 – February 2010: John Mayer

Then came the man who sparked one of her most biting ballads. John Mayer was 12 years Swift's senior, and the duo performed together and smiled for the cameras.

October 2010 – January 2011: Jake Gyllenhaal

A notoriously private pairing, Gyllenhaal and Swift were rarely seen, except for a few golden moments when paparazzi captured them on strolls through Brooklyn.

July 2012 – October 2012: Conor Kennedy

Things got serious fast with Conor Kennedy. Swift was photographed sailing, attending church, kissing, and partying with the Kennedy clan in Hyannis Port, Massachusetts. They even visited a local pizzeria, proving even icons crave pizza and PDA.

November 2012 – January 2013: Harry Styles

The most photographed couple of 2012? Harry Styles and Swift. Their whirlwind romance dominated headlines, but ended quietly…suspiciously quietly.

Styles later confessed, "I don't talk about my personal life in great detail. I write about it in my songs, and I feel like you can share enough about your life in your music to let people know what you're going through."

Rumors swirled of non-disclosure agreements and ironclad silence, fueled by British legal expert Emma Gill, who noted, "Taylor Swift has settled several scores in song, yet cleverly ensured her ex-lovers rarely become liabilities."

February 2015 – May 2016: Calvin Harris

One of the pop icon's longest public relationships was with superstar DJ Calvin Harris. The two walked countless red carpets hand-in-hand, but as quickly as they lit up Hollywood, they burned out.

May 2016 – September 2016: Tom Hiddleston

Enter Tom Hiddleston. Though their relationship was relatively low-key, the pair were occasionally spotted out and about together, drawing attention whenever they appeared in public.

May 2017 – April 2023: Joe Alwyn

Joe Alwyn was the quiet constant in Swift's chaotic world. For six years, they kept their love deeply private until news broke that they had quietly split during her sold-out Eras Tour.

Alwyn's noticeable absence from her concerts raised eyebrows before insiders confirmed the breakup.

May 2023 – June 2023: Matty Healy

One month. That's all it took for The 1975 frontman Matty Healy to be written into the Swift saga. The polarizing pair set tabloids ablaze until Healy's mother quipped, "Obviously, on pain of death, can I talk about that episode, but not being her mother-in-law is a role I'm glad that I lost." Ouch.

Bonus Part – Taylor and Travis Kelce

In the most unlikely love story of the decade, NFL tight end Kelce publicly declared he wanted to meet Swift, and somehow, manifested the relationship of a lifetime. From game-day cuddles to stadium kisses, their chemistry couldn't be denied.

Then, on August 16, 2025, fans' hearts melted when Swift and Kelce shared dreamy engagement photos from a romantic garden proposal.

Swift, glowing in a striped summer dress, held Kelce close as she showed off her massive engagement ring, surrounded by cascading flowers.

From messy splits to elegant silence, heartbreak to healing, and more — Taylor Swift has turned her romantic turmoil into a love story worthy of its own stadium tour.

And now, as she plans her wedding to the man who tackled her heart, fans can't help but wonder: Will this finally be her fairytale ending?