For Millennials. By Millennials.
Taylor Swift’s past relationships have become a topic of interest again after her release of the ‘Red (Taylor’s Version’). In particular, fans of Taylor are talking about her ex-boyfriend Jake Gyllenhaal. Their relationship ended for a multitude of reasons but as hinted in Taylor Swift’s ten-minute version of ‘All Too Well’, their age difference was a major reason for it. Many are calling Jake Gyllenhaal for taking advantage of a young Taylor. But there has also been talk of how Taylor Swift may herself have done the same.
Related: Taylor Swift Celebrates ‘evermore’ Grammy Nomination and ‘All Too Well’ Getting No.1 Spot at The Billboard Hot 100
When a 20 year-old Taylor Swift briefly dated 17-year-old Taylor Lautner
In 2009, Taylor Swift was 20 years old at the time and Taylor Lautner was 17 years old. They met when they starred alongside each other on ‘Valentine’s Day’. They played a couple William Harrington and Felicia Miller. The famous couple dubbed as the Taylor Squared ended up spending a lot of time together and even attending Hockey games. But the two broke up pretty soon, and it seems like it was Swift’s decision to do so. It’s also rumored that her song ‘Back to December’ is about her romance with Taylor Lautner:
“So this is me swallowing my pride / Standing in front of you saying I’m sorry for that night / And I go back to December all the time / It turns out freedom ain’t nothing but missing you / Wishing I’d realized what I had when you were mine.”
And later on in 2010, Taylor Swift had nothing but kind words to say about her ex. When asked who’s her crush, she shared that it was always going to be Taylor Lautner.
Lautner similarly had no bad words to say and called his time with Swift:
It was a fun few months there
He also confirmed that ‘Back to December’ was about him. And at the time, this relationship was legal.
When a 22 year old Taylor Swift dated an 18-year-old Conor Kennedy
In multiple instances in the past, Taylor Swift has dated men that were quite younger than her. In 2012, when she was 22 years old, she met a 17-year-old Conor Kennedy. Conor was a member of the popular and widely known Kennedy family, whom Taylor Swift was in awe of. Taylor Swift was close to Conor’s grandmother Ethel, and it was through her she ultimately met Conor. Conor’s mother had recently died from suicide when he had met Taylor Swift. It was one of the reasons she developed an attachment to Conor, as per J. Randy Taraborrelli’s biography, The Kennedy Heirs:
“Taylor was saddened when she heard the details of how Mary Kennedy had died. She was close to her own mother and couldn’t imagine how Conor was able to go on after facing such tragedy. She admired his strength, his resolve.”
When he turned 18, they started officially dating. At this point, Taylor Swift also bought a house next to his. Which many thought to be an impulsive move on Taylor’s part. A friend of Conor’s shared in the biography:
“Conor liked Taylor, don’t get me wrong, but this business of her buying a house on the Cape made him nervous,” Kennedy’s friend divulged to the writer of The Kennedy Heirs, a biography on the family. “It seemed as if she was getting a little too attached, spending five million bucks on a house just to be near the guy.”
It was after her break-up with Jake Gyllenhaal so people assumed that Taylor Swift was simply over-correcting by dating men younger than her. She had also dated a 32-year-old John Mayer before Jake Gyllenhaal. However, Taylor Swift and Conor Kennedy broke up pretty soon. Taylor Swift ended up selling the house after the break-up. It’s rumored that it happened when Taylor attended a Kennedy family that she was not invited to. But the rumors were shut down by Taylor’s team.
Interestingly enough, the age gap between Conor and Taylor was also a reason the two broke up. As per Taylor’s friend:
“It was like a pendulum for her, swinging back and forth. She dated Jake [Gyllenhaal] and John [Mayer] when she was really young and they were in their 30s, and she got really hurt. So it was like ‘That hurt—this won’t hurt.’ But then it did.”
But the two eventually moved on to other people. Taylor Swift ended up dating One Direction’s Harry Styles.
When a 23-year-old Taylor Swift dated a 19-year-old Harry Styles
Yes, Harry Styles was quite young but he was not underage. Harry Styles and Taylor Swift started their romance in November of 2012. They also dated for only a few months but it was a huge moment for both their fans. The two had met at 2012 Kids Choice Awards. Moreover, Taylor has watched One Direction sing ‘What makes you beautiful’ alongside her close friend Selena Gomez.
Taylor and Harry’s relationship was not publicized as much but he did share in an interview with Seventeen in 2012 that:
“[Taylor]’s a really lovely girl. Honestly, she couldn’t be a sweeter person. She’s a great girl and she’s extremely talented. Some people you meet and they are not as nice as you make them out to be, but she’s one of those people who’s really just amazing.”
The pair were photographed together at a zoo in December 2012, confirming the romance. In early 2013, things started to go sour for Harry Styles and Taylor Swift. A source shared with Daily Mail at the time saying:
“They were on holiday and had an almighty row. They are two young stars at the top of their game so who knows what will happen in the future.”
It seems like they had a fight during the time they were supposed to celebrate New Year’s Eve together. However, things didn’t go as planned. It’s believed that Taylor Swift’s song ‘Style’ is about Harry Styles. The man in the ‘Style’ music video also seemed to be similar looking to Harry Styles. Other songs rumored to be about him were ‘I knew you were trouble’ and ‘Out of the Woods’. Although Taylor didn’t like to name names when talking about her personal life and kept details private, she opened up about her relationship with Harry Styles after a few years:
“It felt very fragile, it felt very tentative. And it always felt like, ‘Okay, what’s the next road block? What’s the next thing that’s gonna deter this? How long do we have before this turns into just an awful mess and we break up?”
Eventually, Harry Styles said that he felt flattered and lucky that Taylor had written songs about him:
“I think about what it means to me to write a song about somebody else and for somebody else to do that, it’s like flattering. Even if the song isn’t that flattering, you still spent time on it and ultimately, using Taylor as an example, she’s a great songwriter. So at least they’re good songs.”
And the two ended up reuniting at the 2021 Grammy Awards and appeared to be on friendly terms.
Currently, Taylor Swift is in a happy relationship with British actor Joe Alwyn. Meanwhile, Harry Styles is in a relationship with actor and director, Olivia Wilde.
In conclusion, Taylor has dated some men that were younger than her but they were very brief romances and she shares no bad blood between her exes.