Let’s be honest: no celebrity dating history gets the internet talking quite like Taylor Swift’s. Over the years, the pop icon has been linked to a seriously A-list lineup — from boy-band heartthrobs to Hollywood actors, indie musicians, and even the occasional unexpected curveball. Basically, if you were a famous guy in the 2010s, the internet wondered if you dated Taylor at some point.
Some of these relationships were full-on public romances that lasted years, while others were blink-and-you-miss-it flings the tabloids obsessed over for about five minutes. And yes, a few of them later showed up as subtle lyrical Easter Eggs in her songs — because Taylor turning life into art is basically pop culture law at this point.
So who exactly has Taylor dated? From her longest relationships to the rumored flings and the unexpected boyfriends you totally forgot about, here’s a complete timeline of Taylor Swift’s dating history — and the famous exes who briefly (or not so briefly) had a starring role in her love life.
How many boyfriends has Taylor Swift had?
Over the years, Taylor Swift has been linked to around 12–13 boyfriends, depending on whether you count rumored flings alongside her confirmed relationships.
Taylor Swift’s Longest Relationships (Ranked)
| Rank | Boyfriend | Length |
|---|---|---|
| 1 | Joe Alwyn | ~6 years |
| 2 | Calvin Harris | ~15 months |
| 3 | Travis Kelce | 2023–present |
Who is Taylor Swift dating now?
As of now, Taylor Swift is *engaged* Travis Kelce, the Kansas City Chiefs tight end. Their relationship went public in 2023 and quickly turned into a full pop-culture moment, with Taylor showing up at NFL games and Travis becoming a regular presence during the Eras Tour era. More on that below!
Taylor Swift’s Relationships Over the Years
Jump to:
- Joe Jonas
- Lucas Till
- Taylor Lautner
- John Mayer
- Cory Monteith
- Jake Gyllenhaal
- Chord Overstreet
- Eddie Redmayne
- Zac Efron
- Conor Kennedy
- Harry Styles
- Calvin Harris
- Tom Hiddleston
- Joe Alwyn
- Matt Healy
- Travis Kelce
Ex: Joe Jonas
Who is He? Singer
Dated In: July – Oct 2008
Joe Jonas holds a pretty iconic spot in Taylor Swift’s dating timeline — he was her first famous boyfriend. The two started dating back in 2008, when both of them were basically teen pop royalty. Their romance didn’t last very long and after about three months together, the relationship ended in a way that quickly became pop culture lore.
Yes, we’re talking about the infamous 27-second phone call breakup. “I’m not even gonna be able to remember the boy who broke up with me over the phone in 25 seconds when I was 18,” she told Ellen DeGeneres at the time.
Fans assumed Joe had cheated on Taylor, especially since he soon moved on to date Demi Lovato. But he later addressed the rumors in a heartfelt message, explaining that there was no cheating involved — his “heart moved on” and his “feelings changed.”
Ex: Lucas Till
Who is He? Actor
Dated In: March – April 2009
Taylor Swift and actor Lucas Till met on the set of her You Belong With Me music video, and sparks briefly flew off-camera too. The two started dating soon after filming, but the romance was pretty short-lived — lasting one month before they decided they were better off as friends.
Lucas later explained what happened in an interview with MTV: “We dated for a little bit. But there was no friction because we were too nice. We just really both liked each other…[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.”
Ex: Taylor Lautner
Who is He? Actor
Dated In: Aug – Nov 2009
In 2009, the internet couldn’t stop talking about “The Taylors.” Taylor Swift and Taylor Lautner met while filming the movie Valentine’s Day and quickly turned their on-screen romance into a real-life relationship. The couple dated for about three months, becoming one of the most talked-about celeb pairings of the time.
But despite sharing the same name (which honestly felt like fate), the relationship reportedly fizzled out because the two just didn’t have much chemistry.
Fast-forward years later, and the exes proved there’s zero bad blood between them. Lautner appeared in Taylor’s I Can See You music video, and he even joined her on stage at The Eras Tour.
Ex: John Mayer
Who is He? Singer
Dated In: Nov – Feb 2010
At one point, Taylor Swift was also linked to singer-songwriter John Mayer — and yes, he was quite a bit older, which definitely got people talking at the time. Their rumored relationship didn’t last long, but the aftermath turned into one of the more dramatic chapters in Taylor’s dating history.
Taylor did what Taylor does best: she turned the experience into music. Fans widely believe her song Dear John was about Mayer, and he later made it clear he wasn’t exactly thrilled about it. Speaking to Rolling Stone, he said: “It made me feel terrible, because I didn’t deserve it. I’m pretty good at taking accountability now, and I never did anything to deserve that. It was a really lousy
Side-note: Taylor’s relationship with John also triggered her never-ending drama with Katy Perry!
SEE ALSO:
Katy Perry’s Dating History – List of Boyfriends
Rumored Ex: Cory Monteith
Who is He? Actor
Dated In: April – May 2010
This one’s more of a “maybe” in Taylor’s dating timeline. Back in 2010, Taylor reportedly had a little spark with Cory Monteith, the late star of Glee. They never officially confirmed a romance, but rumors swirled that her single Mine was inspired by him — a guy she secretly dreamed about dating.
Fans also spotted them hanging out together a few times, from casual bowling nights to late-night dinners, keeping the speculation alive.
Ex: Jake Gyllenhaal
Who is He? Actor
Dated In: Oct 2010 – Jan 2011
In 2010, Taylor Swift had a brief but high-profile fling with Hollywood actor Jake Gyllenhaal, lasting about three months. According to Us Weekly, the relationship ended because Jake wasn’t a fan of the constant camera attention and reportedly could “feel the age difference” — he was 29, Taylor just 21.
The breakup hit Taylor hard. So hard, in fact, that she channeled all that heartbreak into We Are Never Ever Getting Back Together and All Too Well, two of her most iconic breakup anthems.
Rumored Ex: Chord Overstreet
Who is He? Actor
Dated In: February 2011
Okay, this one’s super low-key, but it still counts! Taylor was spotted on a date with Chord Overstreet from Glee, giving him a small spot in her dating timeline. They were seen at an L.A. Kings NHL game, and a source told US Weekly, “After the event, Taylor and Chord grabbed a bite. He’s into her.”
Not exactly a full-blown romance, but fans love adding him to the list of “might-have-beens.”
Rumored Ex: Eddie Redmayne
Who is He? Actor
Dated In: Oct 2011 – Jan 2012
Taylor Swift allegedly had a three-month fling with Eddie Redmayne, the Oscar-winning Fantastic Beasts actor, around 2011–2012. The reason it didn’t last? Eddie reportedly wasn’t down for a long-distance relationship.
Even today, he denies they ever dated, but back then, reports claimed the sparks flew when Taylor was about to be cast in Les Misérables.
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Rumored Ex: Zac Efron
Who is He? Actor
Dated In: Feb 2012 – March 2012
Taylor and Zac Efron? Swifties really wanted this one to be real, but it was more rumor than romance. The speculation blew up when they were promoting The Lorax, but they quickly shut it down on Ellen DeGeneres’ show — with a parody song to make it official: they were never a couple. Still…can we really say sparks didn’t fly?
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Ex: Conor Kennedy
Who is He? Robert F. Kennedy Jr.’s son
Dated In: July – Sep 2012
Enter a Kennedy into Taylor’s dating saga. Taylor had a brief summer fling with Conor Kennedy, son of Robert F. Kennedy Jr., that lasted less than two months. Their PDA-filled romance played out around the Kennedy compound in Massachusetts, but Conor, only 18 at the time, apparently bailed because Taylor “came on too strong.”
RadarOnline even reported that Taylor was allegedly “obsessed with the idea of dating a Kennedy, than the actual Kennedy she was dating.” And fans love pointing out that her Blank Space music video seems to be a nod to this whirlwind romance.
Ex: Harry Styles
Who is He? Singer
Dated In: Dec 2012 – Jan 2013
Taylor Swift’s ex-boyfriends really are what dreams are made of. Back in 2012, Taylor had Directioners losing it when she dated Harry Styles. The popular stars were spotted hand-in-hand at the Central Park Zoo and even kissing on New Year’s Eve, making them one of the most iconic young celebrity couples of the decade.
Sadly, the romance only lasted one month, but it left a huge mark. Taylor channeled the heartbreak into her album 1989 and even gave fans little Easter eggs about them in the Style music video. Honestly, we have a feeling this one stung the most.
Ex: Calvin Harris
Who is He? DJ
Dated In: March 2015 – June 2016
After officially flying solo for over a year, Taylor Swift jumped back into the dating game with DJ Calvin Harris in March 2015. Their relationship lasted until June, and it was full-on public couple energy — matching outfits, sweet anniversary posts, and even making the 2015 list of the highest-paid celebrity couples with combined earnings over $146 million!
Things got messy later, though. Marked as one of Taylor’s famous feuds, Calvin accused her of trying to make him “look bad” and “bury him like Katy Perry,” amid rumors of her dating Tom Hiddleston. In hindsight, Calvin told GQ, “It was the wrong situation. It clearly wasn’t right, so it ended.”
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Ex: Tom Hiddleston
Who is He? Actor
Dated In: June 2016 – Sep 2016
Just two weeks after her breakup with Calvin Harris, Taylor was already linked to another ridiculously handsome celebrity: Marvel actor Tom Hiddleston. And let’s just say…this relationship was anything but low-key (Marvel fans, if you know, you know).
The romance rumors exploded when the pair were photographed kissing on a beach in 2016, and from there, the relationship went fully public. Over the next few months they were spotted everywhere together — from dancing at a Selena Gomez concert to Tom wearing the now-iconic “I ♥ T.S.” tank top during a Fourth of July party.
Sadly, the whirlwind romance didn’t last long. After about three months, the couple split, with reports claiming Tom “wanted the relationship to be more public than she was comfortable with.”
Ex: Joe Alwyn
Who is He? Actor
Dated In: May 2017 – April 2023
Taylor clearly has a soft spot for British men. Actor Joe Alwyn — known for films like Billy Lynn’s Long Halftime Walk and The Vanishing (2018 film) — became the longest and most serious relationship in Taylor Swift’s dating history.
The pair dated for six years, keeping their relationship extremely private compared to Taylor’s past romances. Marriage rumors constantly followed them, and fans truly thought this might be the one that lasted forever.
Although the couple eventually split after the relationship reportedly “ran its course,” their low-key approach is believed to be what helped them last so long. Taylor later confirmed that several songs on her album Folklore were inspired by Joe and their relationship.
Ex: Matt Healy
Who is He? Singer
Dated In: May – July 2023
First rumors of Taylor Swift dating Matt Healy from The 1975 popped up back in 2014, though nothing was ever confirmed. Matt admitted to “exchanging numbers” with her at the time: “We exchanged numbers. Let’s see what happens. I mean bloody hell, what am I going to do? Go out with Taylor Swift? She’s a sensation, I wouldn’t say no.”
Fast forward to May 2023, and the two were spotted holding hands and reportedly kissing on a private NYC date. The Sun’s sources gushed, “It’s super-early days, but it feels right…[they’re] madly in love.”
But, as quickly as it started, it ended. Just two months later, People reported: “They are absolutely not together and aren’t even in contact anymore. She is enjoying being single and has been spending time in the studio and hanging out with friends…”
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Fiancé: Travis Kelce
Who is He? American footballer
Dated In: Sep 2023 – now
Taylor Swift surprised everyone by entering her NFL era with Travis Kelce, the Kansas City Chiefs tight end.
Dating rumors first started in September 2023, when Taylor was spotted cheering at one of Travis’s games. The two were later photographed leaving together and reportedly heading to a private dinner — instantly sending both the Swifties and the NFL internet into meltdown mode.
Not long after, Taylor confirmed the timeline herself in an interview with Time: “We actually had a significant amount of time that no one knew, which I’m grateful for, because we got to get to know each other. By the time I went to that first game, we were a couple.”
From there, their relationship became one of the biggest celebrity storylines in the world. Taylor was regularly spotted cheering for Travis at Kansas City Chiefs games, while Travis returned the support by attending multiple stops of her The Eras Tour.
In 2025, the couple blew up the internet by confirming their engagement, and now fans are eagerly waiting as reports suggest their wedding is set to take place later this year.
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Looking back at Taylor Swift’s dating history, it’s basically a timeline of pop culture moments — from whirlwind flings and headline-making breakups to long-term loves that had fans rooting for her. Some relationships lasted only weeks, others years, but almost all of them became part of the internet’s collective memory.
Now, with her engagement to Travis Kelce, it looks like Taylor may have finally found her real-life happy ending. And if there’s one thing we know about Taylor, it’s that every chapter — heartbreak, romance, and everything in between — eventually becomes part of the story.
Originally published in November 2015.
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