It's 2026, and if you haven't seen the photos of Taylor Swift and Travis Kelce looking basically inseparable in Beverly Hills this week, you might be living under a rock. They’ve been the "it" couple for a while now. But before the Super Bowl rings and that massive engagement announcement in August 2025, the road was... well, it was a lot.
People love to keep track of her exes like they're stats in a game. Honestly? It’s kind of wild how much we remember. From the 27-second phone calls to the scarves left at sisters' houses, the history of who all has taylor swift dated is essentially the roadmap to some of the biggest pop songs of the last two decades.
The Early Days: High School and the First Heartbreaks
Before she was selling out stadiums globally, Taylor was just a kid in Pennsylvania and Nashville writing about the boys in her class. Most people forget about the "non-famous" ones.
- Drew Dunlap: Her high school sweetheart. He’s the guy behind "Tim McGraw." They broke up because he went off to college. Standard teenage stuff, really.
- Jordan Alford: Mentioned in "Picture To Burn." He was the "redneck" who wouldn't let her drive his truck.
- Sam Armstrong: This one was messy. He cheated, she found out, and we got "Should've Said No." It was the first time she used the liner notes to call someone out—capitalizing his name in the lyrics.
Then there was Drew Hardwick. Most fans think they dated, but they didn't. He was the subject of "Teardrops on My Guitar," the guy who'd talk to her about another girl he liked while she just sat there and took it. Classic friend-zone material.
The Hollywood Era: JoBros, Werewolves, and Mayer
The moment "Love Story" blew up, her dating life moved from the classroom to the red carpet.
In 2008, she dated Joe Jonas. It lasted about four months and ended with that infamous phone call. She went on Ellen and told the whole world it took 27 seconds for him to dump her. Flash forward to today, and they’re actually friendly—he even got a shoutout in "Invisible String."
Then came Taylor Lautner in 2009. They met on the set of Valentine's Day. Fans called them "Taylor Squared." This is one of the few relationships where she actually apologized in song. "Back to December" is basically a public "my bad" for how she treated him. Lautner’s still a fan favorite; he even did a backflip on stage during the Eras Tour a couple of years ago.
The John Mayer Situation
This one was different. It wasn't puppy love. Taylor was 19, and John Mayer was 32. They collaborated on "Half of My Heart," and things got romantic fast. It ended badly. "Dear John" is one of her most scathing tracks, and in 2022, she revisited those feelings with "Would've, Could've, Should've." It's clear that age gap left a mark.
The "Red" and "1989" Years: Gyllenhaal to Styles
If you want to know who all has taylor swift dated during her peak "indie-pop" transition, you have to talk about Jake Gyllenhaal. They dated for a few months in 2010. He’s the reason "All Too Well" exists. He skipped her 21st birthday party, and the rest is history.
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2012 brought Conor Kennedy. Yes, as in the Kennedys. She was 22, he was 18. It was a whirlwind summer in Hyannis Port. She even bought a house nearby. It didn't last through the fall, but it gave us "Begin Again."
Then came Harry Styles. "Haylor" was short-lived—only about a month or two—but the impact was massive. That New Year’s Eve kiss in Times Square? The snowmobile accident? It’s all in the songs "Style" and "Out of the Woods."
The Longest Run: Calvin, Tom, and the Six-Year Secret
For a while, things got quiet.
Calvin Harris was her longest relationship for a long time—15 months between 2015 and 2016. It ended with a lot of Twitter drama over who wrote "This Is What You Came For." Then, in a move nobody saw coming, she danced with Tom Hiddleston at the Met Gala. They dated for a "Getaway Car" summer. He wore the "I Heart T.S." shirt. The internet cringed. It fizzled.
Then she disappeared.
Enter Joe Alwyn. They stayed together for six years. From 2016 to early 2023, they were a ghost couple. They barely ever did red carpets. He helped her write songs under the name William Bowery. Everyone thought they were the endgame. When the news broke in April 2023 that they'd split because the relationship "ran its course," the fandom actually went into mourning.
The 2023 Pivot: Matty Healy and the NFL
The summer of 2023 was chaotic. Right after Joe, she had a brief, high-profile fling with Matty Healy from The 1975. It lasted about a month, but it caused a massive stir. When The Tortured Poets Department dropped in 2024, fans realized a lot of those heartbreak songs were actually about him, not Joe.
But then, the friendship bracelet happened.
Travis Kelce tried to give her his number at her Kansas City show in July 2023. He failed. He talked about it on his podcast. She reached out. By September, she was at a Chiefs game. By 2024, they were kissing on the field at the Super Bowl.
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Where They Are Now (January 2026)
As of right now, Taylor and Travis are officially engaged. They announced it back in August 2025 with a post set to "So High School." The Chiefs might be out of the playoffs this season, but Travis is reportedly spending his downtime in L.A. with Taylor, planning a June wedding.
Summary of Major Relationships
| Era | The Partner | Noteworthy Detail |
|---|---|---|
| Debut | Joe Jonas | The 27-second breakup call. |
| Fearless | Taylor Lautner | The apology in "Back to December." |
| Speak Now | John Mayer | Significant age gap; "Dear John." |
| Red | Jake Gyllenhaal | The infamous "All Too Well" scarf. |
| 1989 | Harry Styles | Paper airplane necklaces and 1950s style. |
| Reputation | Calvin Harris | High-profile DJ; messy social media split. |
| Folklore/Evermore | Joe Alwyn | Six-year relationship; co-wrote songs. |
| TTPD | Matty Healy | A short, controversial summer romance. |
| Present | Travis Kelce | NFL star; engaged as of August 2025. |
Learning about who all has taylor swift dated isn't just about gossip. It's about seeing how her music evolved from teenage diary entries to complex, adult reflections on love and fame.
If you're trying to keep up with the latest, keep an eye on the June 2026 calendar. All signs point to a wedding that might just break the internet. For now, you can catch up on her history by listening through her re-recordings—the "Taylor's Versions"—where she often adds "From the Vault" tracks that give even more context to these past chapters.