Home EntertainmentCelebrity A First Down Comes Before a Touchdown: Top 5 Taylor Swift Ex-Boyfriends

A First Down Comes Before a Touchdown: Top 5 Taylor Swift Ex-Boyfriends

by Scott Kacsmar
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Taylor Lautner Taylor Swift

Taylor Swift is living her best life right now with a record 4th Grammy award for Album of the Year, a hugely successful World Eras tour, and she won the Super Bowl for the Kansas City Chiefs.

Well, that’s at least a popular theory about what happened in the NFL this year after Swift started dating superstar tight end Travis Kelce of the Chiefs. She attended her 1st game in Week 3 to confirm there was a relationship developing. By Super Bowl LVIII, she was at her 13th game, her lucky number, to see Kelce and the Chiefs end the longest drought in NFL history without a repeat champion.

Now with Kelce in offseason mode, the star couple might finally get some real time together as she has been busy touring, and he was busy playing championship football. It was back in July when Kelce shot his shot to Swift on his podcast, and they allegedly started seeing each other soon after that leading into the season.

So, this relationship has been going on for at least 6 months, which already gives Kelce more staying power than some of Swift’s past famous flings, including Harry Styles, Jake Gyllenhaal, and Joe Jonas.

Kelce already has 3 Super Bowl rings, but can he pull this one off too, or will he join Swift’s list of famous ex-boyfriends and become the inspiration for her next album’s break-up songs?

Kelce has his work cut out for him now that football’s over, so we thought this would be a good time to rank Taylor Swift’s top 5 ex-boyfriends. For fun, we compared each ex to another NFL tight end to put them in context with Kelce.

And if you’re wondering if you can bet on Swift, you’ll be happy to know that many of the top betting sites do offer props on the singer’s personal life.

5 Taylor Lautner

Taylor Swift Taylor Lautner

  • Relationship Period: August to November 2009
  • NFL Tight End Comparison: Todd Christensen

One of Swift’s earliest celebrity boyfriends, actor Taylor Lautner was enjoying the limelight in 2009 with the success of Twilight where he played werewolf Jacob. Anyone who could give Robert Pattinson a run for his money in drawing the attention of teenage fans has to be given some props.

Lautner caught Swift’s attention when they played a high school couple in the movie Valentine’s Day. The two dated for a few months in 2009 before she allegedly ended things as stated in her song “Back To December.”

But they remain on good terms, with Lautner making appearances in her music video and at her Eras tour. Lautner’s wife is also a Swiftie, so everything worked out in the end.

Our NFL tight end comparison for Lautner is Raiders’ great Todd Christensen, who was one of the top tight ends in the league in 1983-87 when he made 5 straight Pro Bowls and led the league in receptions twice.

But his run of success was short-lived just as Lautner’s, who didn’t do much as an actor outside of that peak run during the Twilight saga (2008-12).

4 Tom Hiddleston

Taylor Swift Tom Hiddleston

  • Relationship Period: Summer 2016
  • NFL Tight End Comparison: Kellen Winslow Sr.

While it only lasted briefly in the summer of 2016, “Hiddleswift” was rumored to be a publicity stunt, just like people have said about Kelce and Swift this year. But the actor known for playing Loki in the MCU was reportedly smitten with the singer, and their breakup was far less messy than her other trysts with older men such as John Mayer and Jake Gyllenhaal.

Maybe Hiddleston shouldn’t have worn the “I Heart T.S.” t-shirt shortly before the couple’s demise, but he has been supportive of her in the years since.

Our NFL tight end comparison for Hiddleston is Chargers’ legend Kellen Winslow, a 1st-round pick and Hall of Fame member. He rocked the Power Blue jersey just like Hiddleston’s blue eyes steal scenes. Winslow was a prolific receiver and helped the Air Coryell offense reach historic heights, just like how The Avengers wouldn’t be the same if not for Hiddleston’s performance as Loki.

3 Joe Jonas

Taylor Swift Joe Jonas

  • Relationship Period: July to October 2008
  • NFL Tight End Comparison: Sam LaPorta

You (probably) always remember your first celebrity boyfriend. The Jonas Brothers were popular in 2008 and Swift was also still a young, breakout artist after her debut album came out in late 2006. The couple only dated for a few months before he allegedly ended things with the 18-year-old via a 27-second phone call.

But it had such an effect on Swift that she ended up writing songs about Jonas for her 2008 album Fearless and again on her 2010 album Speak Now. He clearly left a mark, for better or worse.

But with instant success, our NFL tight end comparison for Jonas is Sam LaPorta, the Detroit Lions rookie who just set an NFL record with 86 catches as a rookie tight end. He also had 889 yards and 10 touchdowns, so he came out on fire to start his career. We’ll see if he can keep it going.

At least Jonas is reportedly on good terms with Swift today.

2 Joe Alwyn

Taylor Swift Joe Alwyn

  • Relationship Period: May 2017 to April 2023
  • NFL Tight End Comparison: Marcedes Lewis

The ironman of the group, English actor Joe Alwyn is not a household name like many of these other boyfriends. His IMDb page says I’ve seen him in 3 films and I wouldn’t be able to pick him out of a lineup, so he’s not the most impressionable actor or someone who gets many leading roles.

But Alwyn was with Swift for 6 years and looked like he might be the one, given none of her other ex-boyfriends made it past a year. Fans were surprised when things ended in 2023. Swift’s new album, The Tortured Poets Department, is allegedly going to be about Alwyn, so he’ll get his break-up song(s) while she’s at the peak of her career. Good luck, king.

We have to reward the longevity here, though. That is why our NFL tight end comparison for Alwyn is Marcedes Lewis, a 1st-round pick in 2006 who was still in the league this past year with Chicago. He hopes to return for his age-40 season in 2024 too, so Kelce, who will be 35, has some real competition on the longevity front here.

But Lewis has only made the Pro Bowl once in his 18 years when he had a career-high 700 yards for the Jaguars in 2010. Lewis is no Kelce, and we’ll see if Travis is indeed the lifetime answer for Swift that Alwyn was not.

1 Jake Gyllenhaal

Taylor Swift Jake Gyllenhaal

  • Relationship Period: October 2010 to January 2011
  • NFL Tight End Comparison: Rob Gronkowski

There was always some concern with Swift dating another man with a solid 10 years on her after the disastrous relationship with John Mayer, a musician that’s always been overrated to me.

But Gyllenhaal came at an interesting time in her life in late 2010, and the couple reportedly spent Thanksgiving at his sister’s place. But he also allegedly missed her 21st birthday party. The age gap did indeed lead to the couple splitting in January, and that led to a popular Swift song “All Too Well” that references her scarf that Gyllenhaal has been seen wearing over the years. Maybe he just really likes the scarf?

Our NFL tight-end comparison for Gyllenhaal is Rob Gronkowski. Both did their best work in the 2010s when Gronk was a 3-time Super Bowl-winning stud for the Patriots, and Gyllenhaal had an incredible run of films with Source Code, End of Watch, Prisoners, Enemy, Nightcrawler (his best work ever), and the underrated Nocturnal Animals.

They may not have worked out as a couple, but you could say the end of their relationship inspired Gyllenhaal and Swift to raise their careers to a much higher level with some of their absolute best work in the 2010s.

We’ll see if Swift can inspire Kelce to reach even deeper in his age-35 season in 2024 and help the Chiefs do something that’s never been done before – win 3 straight Super Bowls. That might prompt Kelce to retire on the spot and propose to Swift on the stage at the big game.

But he has a long way to go before that can happen as evidenced by her extensive list of famous ex-boyfriends.

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Scott Kacsmar
NFL football picks are Scott Kacsmar's expertise, serving as his main focus. He has contributed to various sports websites and blogs, such as NBC Sports, ESPN Insider, FiveThirtyEight, and, JoeWager. Originating from Pittsburgh, Scott maintains a love-hate connection with the Pirates.

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