Toucher & Rich

Toucher & Rich

Weekdays 6am-10am

(DISCLAIMER: Could this article be the dumbest piece of work i’ve ever constructed in the 7+ years working at the Sports Hub? Most likely, yes. I gotta collect those clicks so I can feed baby Noah. What better way of getting clicks then writing an article about Taylor Swift?)

Pop sensation Taylor Swift is known for weaving her personal life into her music, particularly her love life. As we all know, Taylor often turns to music to express her feelings about love and breakups. Now that she’s in a relationship with star athlete Travis Kelce, let’s take a look at Taylor’s past romances and see how the Chiefs tight end fits into her exclusive list of celebrity partners.

Taylor Swift

KANSAS CITY, MISSOURI – SEPTEMBER 24: Taylor Swift reacts during the first half of a game between the Chicago Bears and the Kansas City Chiefs at GEHA Field at Arrowhead Stadium on September 24, 2023 in Kansas City, Missouri. (Photo by Jason Hanna/Getty Images)

Travis Kelce is quite different from Taylor Swift’s usual partners (I would know being an well-renowned Taylor Swift expert). In fact, Travis is the first professional athlete known to have dated the pop queen. Taylor is typically associated with prominent figures in the music and film industries, so her newfound connection with an athlete like Travis has surprised many, given her dating history with more artistically inclined individuals.


KANSAS CITY, MISSOURI – SEPTEMBER 24: Travis Kelce #87 of the Kansas City Chiefs looks on prior to a game against the Chicago Bears at GEHA Field at Arrowhead Stadium on September 24, 2023 in Kansas City, Missouri. (Photo by Jason Hanna/Getty Images)

With that said, I’m here to provide you with a comprehensive list of Taylor Swift’s former boyfriends, the songs she has penned about them, and whether I consider them a “hunk” or “cutie pie.” We’ll also assess how Travis Kelce measures up to this illustrious group.

  • Joe Jonas (July 2008 - October 2008)


    MIAMI BEACH, FLORIDA – MAY 05: Joe Jonas of the Jonas Brothers speaks during SiriusXM Hits 1 Celebrity Session at SiriusXM Studios on May 05, 2023 in Miami Beach, Florida. (Photo by Emma McIntyre/Getty Images for SiriusXM)

    Broke up over a 27-second phone call. Inspired songs like “Forever & Always” and “Last Kiss.”

    Hunk or cutie-pie: barely a cutie pie.

    Kelce or Jonas: Kelce.

  • Taylor Lautner (August 2009 - November 2009)


    LOS ANGELES, CA – NOVEMBER 14: Actor Taylor Lautner arrives at Summit Entertainment’s “The Twilight Saga: Breaking Dawn – Part 1” premiere at Nokia Theatre L.A. Live on November 14, 2011 in Los Angeles, California. (Photo by Frazer Harrison/Getty Images)

    Met on the set of “Valentine’s Day.” Inspired by the song “Back to December.”

    Hunk or cutie-pie: Neither.

    Kelce or Lautner: c’mon

  • John Mayer (November 2009 - February 2010)


    LOS ANGELES, CALIFORNIA – OCTOBER 31: John Mayer performs onstage during “Mac Miller: A Celebration Of Life” Concert Benefiting The Launch Of The Mac Miller Circles Fund at The Greek Theatre on October 31, 2018 in Los Angeles, California. (Photo by Kevin Winter/Getty Images for LiveNation)

    Their breakup reasons weren’t confirmed. Inspired the song “Dear John.”


    Kelce or Mayer: Mayer and it’s not even a debate.

  • Jake Gyllenhaal (October 2010 - December 2010):


    LOS ANGELES, CALIFORNIA – APRIL 17: Jake Gyllenhaal attends the Los Angeles Premiere of MGM’s Guy Ritchie’s “The Covenant” at Directors Guild Of America on April 17, 2023 in Los Angeles, California. (Photo by Jon Kopaloff/Getty Images)

    Broke up due to Jake’s change of feelings and media attention. Inspired songs on the “Red” album, notably “All Too Well.”

    Hunk or cutie-pie: Hunk. Bad boy hunk because he broke Taylor’s heart.

    Kelce or Gyllenhaal: This is tough. Are we talking Prisoner Jake or Nightcrawler Jake? If we’re talking Prisoner Jake Gyllenhall, gimme dat!

  • Conor Kennedy (July 2012 - October 2012)


    BEL AIR, CALIFORNIA – FEBRUARY 04: (L-R) Conor Kennedy and Giulia Be attend 2023 Roc Nation The Brunch at Private Residence on February 04, 2023 in Bel Air, California. (Photo by Momodu Mansaray/Getty Images for Roc Nation)

    Ended due to long-distance issues following his mother’s death.

    Hunk or cutie-pie: Does nothing for me.

    Kelce or Kennedy: Kelce.

  • Harry Styles (December 2012 - January 2013)


    PARIS, FRANCE – MARCH 13: In this handout photo provided by Helene Marie Pambrun, Harry Styles performs during his European tour at AccorHotels Arena on March 13, 2018 in Paris, France. (Photo by Handout/Helene Marie Pambrun via Getty Images)

    Ended with a heated argument during a vacation. Taylor left early.

    Hunk or cutie-pie: He’s the definition of a cutie-pie.

    Kelce or Styles: I’m going with Styles. Usually i’m not a cutie pie kinda guy. He just seems like a fun hang.

  • Calvin Harris (March 2015 - June 2016)


    NEW YORK, NY – DECEMBER 07: Calvin Harris performs at Z100’s Jingle Ball 2018 at Madison Square Garden on December 7, 2018 in New York City. (Photo by Dia Dipasupil/Getty Images for iHeartMedia)

    Broke up due to various factors, with the song “This Is What You Came For” playing a role.

    Hunk or cutie pie: Hunk, I guess?

    Kelce or Harris: Kelce. Not a fan of the techno.

  • Tom Hiddleston (June 2016 - September 2016)


    LAS VEGAS, NEVADA – APRIL 03: Actor Tom Hiddleston attends the 51st Academy of Country Music Awards at MGM Grand Garden Arena on April 3, 2016 in Las Vegas, Nevada. (Photo by David Becker/Getty Images)

    Breakup attributed to media pressure. Inspired the song “Getaway Car.”

    Hunk or cutie pie: LOKI.

    Kelce or Hiddleton: LOKI.

  • Joe Alwyn (September 2016 - March 2023)


    WEST HOLLYWOOD, CALIFORNIA – MAY 17: Joe Alwyn attends a Special Screening for Hulu’s “Conversations With Friends” at Pacific Design Center on May 17, 2022 in West Hollywood, California. (Photo by Jon Kopaloff/Getty Images)

    Their almost seven-year relationship ended abruptly. Taylor wrote songs like “Lover” and “Cornelia Street” dedicated to him. She initiated the breakup during The Eras Tour.

    Hunk or cutie pie: Who?

    Kelce or Alwyn: Seriously, who’s Joe Alwyn?

Sign me up for the 98.5 The Sports Hub email newsletter!

Get the latest Boston sports news and analysis, plus exclusive on-demand content and special giveaways from Boston's Home for Sports, 98.5 The Sports Hub.

By clicking "Subscribe" I agree to the website's terms of Service and Privacy Policy. I understand I can unsubscribe at any time.