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Boyfriends (Taylor’s Version)

Updated: Apr 17, 2023

Image credits: Pinterest


Happy Valentine's Day! I compiled a playlist of songs Taylor has written for previous and current boyfriends, and put the songs in order for her timeline. I thought today would be the perfect day to share the songs, both of love and of heartbreak.



Joe Jonas (2008)

Image credits: Pinterest


Taylor's first public boyfriend was Joe Jonas, who famously broke up with her over a 27-second voicemail.


Notable songs:

"Forever and Always" (Fearless)

"Last Kiss" (Speak Now)

"Holy Ground" (Red), which is her looking back on the relationship in a positive light.

"Mr. Perfectly Fine" (Fearless)


Taylor Lautner (2009)

Image credits: Elle


The two met when they co-starred together in "Valentine's Day," where they played a high school couple.


Notable songs:

"Back to December" (Speak Now)

"your tanned skin, your sweet smile"

John Mayer (2009)

Image credits: Popcrush


Who could forget the infamous John Mayer, who dated 19 year-old Taylor when he was 32? After their messy breakup, John Mayer popularly said in a Rolling Stone Interview: "I will say as a songwriter that I think it's kind of cheap songwriting" about Taylor's "Dear John" which he confirmed was about him.


Notable songs:

"Superman" (Speak Now)

"Ours" (Speak Now)

"The Story of Us" (Speak Now)

"Dear John" (Speak Now)

"Would've, Could've, Should've" (Midnights)


Jake Gyllenhaal (2010-2011)

Image credits: The Verge


The boyfriend who prompted an entire 10-minute song about the way he treated and gaslit Taylor. The rumor is that the 10-year age gap wasn't working, so Jake broke up with her. In "All Too Well" (10 Minute Version), Taylor says "you said if we had been closer in age maybe it would have been fine, and that made me want to die"


Notable songs:

"All Too Well" (10 Minute Version) (Red)

"The Last Time" (Red)

"I Knew You Were Trouble" (Red)

"I Bet You Think About Me" (Red)


Conor Kennedy (2012)

Image credits: Elle


Taylor dated Conor throughout the summer of 2012, though the two broke up as the Kennedy family accused Taylor of crashing his cousins wedding (which her reps denied).


Notable songs:

"Begin Again" (Red)


Harry Styles (2012-2013)

Image credits: Pinterest


This was one of Taylor's most popular relationships, and it produced many songs about the couple. After a year-long on-and-off breakup, the two broke up for good in 2013. Shortly after, Taylor posted a picture of her in a recording studio.


I also have a playlist about songs they each wrote for their relationship, and it has even more songs than I added on this.



Notable songs:

"Message In A Bottle" (Red)

"Come Back... Be Here" (Red)

"This Love" (Red)

"I Know Places" (1989)

"Out Of The Woods" (1989)

"Style" (1989)

"Wonderland" (1989)

"We Never Go Out Of Style" (Red)

"Maroon" (Midnights)

"Question...?" (Midnights)


Calvin Harris (2015-2016)

Image credits: Vanity Fair


Calvin and Taylor's relationship was one of her most pictured; there are many red carpet appearances and social media posts together.


Notable songs:

"High Infidelity" (Midnights)


Tom Hiddleston (2016)

Image credits: Popsugar


I previously wrote a blog post about this romance, which tells of their whirlwind relationship that abruptly ended after Hiddleston allegedly proposed. Taylor met Tom at the Met Gala, and the two were pictured dancing together while she was still dating Calvin. "High Infidelity" is said to be loosely based off of this event.


Notable songs:

"Getaway Car" (Reputation)

"Champagne Problems" (Evermore)

"Cowboy Like Me" (Evermore)

"Midnight Rain" (Midnights)


Joe Alwyn (2016-Present)

Image credit: Hollywood Life


The two have been keeping their romance much more private than Taylor has in the past, but Joe has certainly been with Taylor the longest and has the most positive songs written about him. If you follow Joe on Instagram, you can see the occasional posts of Taylor's cats to remind you they live together.


Notable songs:

"...Ready For It?" (Reputation)

"Gorgeous" (Reputation)

"King Of My Heart" (Reputation)

"Dress" (Reputation)

"Call It What You Want" (Reputation)

"Lover" (Lover)

"I Think He Knows" (Lover)

"London Boy" (Lover)

"Afterglow" (Lover)

"Invisible String" (Folklore)

"Peace" (Folklore)

"The Lakes" (Folklore)

"Willow" (Evermore)

"Long Story Short" (Evermore)

"Lavender Haze" (Midnights)

"Snow On The Beach" (Midnights)

"Labyrinth" (Midnights)

"Sweet Nothing" (Midnights)

"The Great War" (Midnights)

"Paris" (Midnights)

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