Who Did Taylor Swift Date At 19?
2022 Toronto International Film Festival - In Conversation With... Taylor Swift
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Who Did Taylor Swift Date At 19?

Rachael Grealish October 21, 2022

Taylor Swift’s tenth studio album, Midnights, has finally dropped and it has fans asking who did the superstar date at 19.

Today, October 21, Taylor Swift dropped her new album Midnights which features 13 tracks. There are 20 on the 3am Edition which she announced at, you guessed it, 3am as a “chaotic” surprise to fans.

Photo by Dimitrios Kambouris/Getty Images for MTV/Paramount Global

However, there’s one track on the bonus songs that has fans questioning the 32-year-old’s dating history when she was a teenager. That track is “Would’ve, Could’ve, Should’ve”.

Taylor Swift Would’ve, Could’ve, Should’ve

In the bonus track song on Midnights, “Would’ve, Could’ve, Should’ve” the 11-times Grammy Award winner seems to sing about a relationship she had at age 19, describing it as “dancing with the devil”.

Swift sings: ‘And I damn sure would’ve never danced with the devil/ At 19, and the God’s honest truth is that the pain was heaven/ And now that I’m grown, I’m scared of ghosts/ Memories feel like weapons/ And now that I know, I wish you left me wondering.’

She also sings about how she “misses who she used to be” and says the person this song is about took her “girlhood” as she sings: ‘Give me back my girlhood, it was mine first.’

Who did Taylor Swift date at 19?

With lyrics literally calling out an age, 19, it has fans asking who Taylor Swift dated when she was that age and theorizing the song could be about that person.

Photo by Dimitrios Kambouris/Getty Images for VEVO

When she was 19 Swift sparked up a romance with the then-31-year-old singer John Mayer. It wasn’t kept quiet and the pair were often spotted together on the red carpet. Their romance was brief, but it clearly struck a nerve with the teenage singer as it’s often thought the song “Dear John”, from her 2010 album Speak Now, was about none other than Mayer.

This is because in the song she sings: ‘Dear John, I see it all, now it was wrong/ Don’t you think nineteen is too young/ To be played by your dark twisted games, when I loved you so?’

Then Mayer pretty much confirmed the whole thing when he later spoke to Rolling Stone magazine saying: ‘“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 thing for her to do.’

As she was 19 when she started dating Mayer and “Would’ve, Could’ve, Should’ve” describes a person going through a relationship that changed then at 19, fans are quick to put out their theories.

Both Taylor Swift and John Mayer have been contacted by GRV Media for a comment.

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Rachael is the Senior Content Editor at Freshered. She is NCTJ qualified with an MA in journalism. Rachael has almost ten years experience as a journalist in regional, national and international press and is passionate about creating engaging content.