All The Men Taylor Swift Has Dated So Far (As of 2023)

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Taylor Swift is one of the biggest pop stars, performing her hits to packed stadiums. One of the biggest inspirations for her music is the men she’s dated – and there are quite a few on the list so far.

If you’re interested in learning more about all the men Taylor Swift has dated so far, sit down and get ready as we dive into 15 people who have found themselves in Taylor Swift’s life.

1. Brandon Borello 

taylor swift on the red carpet in 2008
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First on our list of all the men Taylor Swift has dated so far is Brandon Borello, the first boyfriend she dated in high school. They broke up in 2008 because of the distance due to college, pushing them in different directions. There were a couple of other high school boyfriends that appeared, but Brandon Borello was the sweetest for Swift.

2. Joe Jonas

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Taylor Swift and the iconic Joe Jonas started dating in 2008, dating from July to October of the same year. It was a very public breakup, completed by Jonas over a 27-second call on the phone. She reports it was painful then, but she’s since grown to look fondly on it. Now, all that remains of the relationship is the infamous phone call and the resulting breakup.

Related: 18 Best Sibling Bands

3. Lucas Till

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Lucas Till is next on our list of all the men Taylor Swift has dated so far, meeting the singer when he appeared in her music video for “You Belong With Me”. They dated for a short period from March to April 2009, on and off again, stating they were better off as friends instead of boyfriend and girlfriend at that stage in their life. 

4. Taylor Lautner

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Taylor Lautner met Taylor Swift when they starred together in the movie Valentine’s Day, portraying a high school couple desperately in love. They dated from August to December of 2009 until they realized their relationship wasn’t headed in the right direction, and they broke it off, inspiring the song “Back To December”. 

5. John Mayer

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John Mayer was a prominent but brief figure in Taylor Swift’s life, linking when they worked together on the song “Half of My Heart.” They dated from December 2009 to February 2010, breaking up thanks to irreconcilable differences largely due to their 13-year age gap. She was bitter about the break-up, writing songs like “Dear John” afterward.

Related: 12 Best John Mayer Songs

6. Cory Monteith 

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Although it was never officially confirmed, Swift reportedly dated the late Cory Monteith for a short period after they were photographed together at a Grammys party. They never confirmed anything and were not seen together for long after the picture took place. Sadly, Monteith passed away a few years later.

7. Jake Gyllenhaal

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Next up was the infamous Jake Gyllenhaal, a quiet relationship that started with a bang when Gyllenhaal spent $160,000 to fly her over in a private jet for a date. They were together from October 2010 to January 2011, but it may have ended with an emotional bang based on her music video for her song “All Too Well,” acted out by Sadie Sink and Dylan O’Brien.

8. Adam Young

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This one partially counts – Taylor Swift and Adam Young never really dated, but they did exchange some emails in 2011 that escalated into one face-to-face meeting between the musical talents. She loved the interaction so much that she supposedly wrote the song “Enchanted” about him. However, it never escalated beyond that point.

9. Chord Overstreet

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Taylor Swift went on a single date with Chord Overstreet in 2011, and pictures were taken. They never went out again after the sweet, documented moment.

10. Connor Kennedy

taylor swift on the red carpet in 2018
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Taylor Swift casually astonished the world when she was photographed with Connor Kennedy in Hyannisport, Massachusetts, being very friendly with each other. She met him after meeting his aunt the year before, who later brought the two together. They started dating in July 2012 and broke up in October of the same year due to the distance.

11. Harry Styles

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The iconic Harry Styles briefly had a relationship with Taylor Swift in November 2012 after meeting backstage at the Kid’s Choice Awards and hitting it off. They dated for three months and then broke up in January 2013 after having a massive argument. It was an awkward aftermath, including a Taylor Swift diss towards Harry during the 2013 MTV VMAs.

Related: Are You a Harry Styles Fan?

12. Calvin Harris

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Next on our list of all the men Taylor Swift has dated so far is the DJ Calvin Harris. The two met in 2015 at the Elle Style Awards after being introduced to each other by singer Ellie Goulding. They wore matching outfits, kissed in public, and then broke up in May 2016 after some arguments and an accusation from Harris about Swift cheating on him.

Related: The 15 Greatest DJs of All Time

13. Tom Hiddleston

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In a shocking moment for Marvel fans everywhere, Taylor Swift began dating actor Tom Hiddleston in May 2016. They started hanging out at the Met Gala, then continued their relationship. They canoodled, went on vacation, and danced until they broke up in September of the same year because Swift was afraid he wasn’t with her for the right reason.

14. Joe Alwyn

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Joe Alwyn was the longest relationship Taylor Swift had, lasting from May 2017 to April 2023. They also came together at the Met Gala. They had an incredible relationship, dancing and even attending premieres together. They reported their reason for the split was that the relationship had run its course, and it was the right time.

15. Matt Healy 

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Last on our list of all the men Taylor Swift has dated so far, and the most recent addition to the list, is the lead singer of The 1975, Matt Healy. They were seen holding hands and kissing in New York City in May of 2023, soon after her split with Joe Alwyn. They called it quits less than a month later, possibly due to the controversy that arose because of their connection.

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Written by Hope Davis

Long-time music lover Hope became a full-time writer in 2020 after being laid off from her regular job due to COVID-19. She now spends her time traveling the world to see her favorite bands while writing about them!


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