In this article, I will discuss the fascinating relationships of Taylor Swift, the talented Singer. We will break it down to how old Swift was in every relationship she has ever had; including how old her partners were too.
As we all know by now, Taylor is a singer, songwriter, producer, and businesswoman known for her exploits in the music industry. She boasts an impressive list of accolades, including 12 Grammy Awards, an Emmy Award, 40 American Music Awards (the most ever won by an artist), and many more.
Taylor Swift’s honesty and straightforwardness about her love life have inspired some of her most powerful lyrics, as her relationships have been a driving force behind her music.
Throughout Taylor Swift’s journey in love, she has experienced moments of happiness, regret, and uncertainty. Her relationships have gone past age boundaries, involving both younger and older partners, shaping her romantic narrative.
Taylor tends to date actors or singers, with the exception of Connor Kennedy and Travis Kelce.
Over Taylor’s career, she has been publicly associated with 11 men. Let’s get to know these men below.
- Joe Jonas
Taylor dated American singer-songwriter and actor Joseph Adams Jonas.
Taylor Swift was romantically involved with Joe Jonas of the Jonas Brothers during the summer of 2008. However, their relationship ended a few months later through a phone call from Jonas, who was 19 then.
Reflecting on the breakup during an interview with Ellen DeGeneres, Swift mentioned, “I won’t even remember the guy who broke up with me over the phone in 25 seconds when I was 18… I checked the call log—it was around 27 seconds. That must be some record.”
- Taylor Lautner
Taylor Swift dated Twilight star Taylor Lautner, whom she met on the set on Valentine’s Day.
She and her “Valentine’s Day” movie co-star, Taylor Lautner, were romantically involved from October to December 2009. They started dating when Taylor was 20 and Lautner was 17.
Their relationship ended shortly after Lautner’s 19th birthday party, reportedly due to differing levels of affection, with a source from Us Weekly indicating that Lautner held stronger feelings for Swift.
In Swift’s song “Back to December,” she appeared to reflect on the breakup, expressing sentiments like “I miss your tan skin, your sweet smile,” and acknowledging the regret with lyrics such as “It turns out freedom ain’t nothing but missing you,” and “Wishing I’d realized what I had when you were mine.”
- John Mayer
Taylor Swift also dated John Mayer, a singer, songwriter, and guitarist, despite a 13-year age gap. Taylor pursued the romance, although it didn’t last long.
They briefly dated in 2009 and collaborated on the “Half of My Heart” duet for Mayer’s album. However, after their breakup, Swift released the song “Dear John” in 2010, widely assumed to be about Mayer, who was then linked to Katy Perry.
At 38 years old, Mayer expressed feeling “humiliated” by the song in a June 2012 interview with Rolling Stone, stating, “I never did anything to deserve that. It was a really lousy thing for her to do.”
- Jake Gyllenhaal
American actor Jake Gyllenhaal was also part of Swift’s love life as she dated him briefly in 2010. The American actor was 30 years of age when he dated Taylor, who was 21 years old.
Despite attempts to keep it low-key, paparazzi caught them together multiple times before the relationship seemed to fade by Christmas. Many believe Swift’s track “We Are Never Ever Getting Back Together” is inspired by her time with Jake.
In a 2012 interview with USA Today, Taylor revealed the song was influenced by an ex who “made me feel inadequate compared to the hipster bands he favored.”
- Conor Kennedy
Taylor Swift was also in a romantic relationship with social activist Conor Kennedy.
In the summer of 2012, Taylor dated Conor Kennedy, who was 18 at the time, the son of Robert F. Kennedy Jr. and the late Mary Kennedy, while Taylor was 23.
Their romance flourished briefly before fading away by autumn. They were often seen around the Kennedy family home in Hyannis Port, Massachusetts, engaging in affectionate moments and bonding with his relatives.
Conor’s grandmother, Ethel Kennedy, praised Swift, calling her “sensational inside and out.”
Despite the positive remarks, their notable age gap sparked attention, with rumors circulating that Swift had “abducted” Kennedy by flying him from his Massachusetts boarding school to Nashville using her private jet.
Swift refuted these claims, stating to Rolling Stone, “You can’t kidnap a grown man!”
Their relationship also came to an end after some months.
- Harry Styles
The American music star was also romantically involved with British singer Harry Edward Styles, popularly known as Harry Styles when he was 18 and she was 23.
Taylor began dating One Direction member Harry Styles in November 2012, but their relationship ended in January 2013.
Their brief romance is believed to have inspired two of Swift’s songs: “Style” and “Out of the Woods.”
Prior to a performance of “Out of the Woods,” Swift expressed the anxiety she experienced during that relationship, mentioning in a video released by the Grammy Museum, “The primary feeling I had in that relationship was anxiety. It felt delicate and uncertain, and I was always thinking, ‘What’s the next obstacle? What’s going to ruin this? How long until it becomes a complete mess, and we break up? Is it a month? Is it three days?'”
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- Calvin Harris
The Scottish DJ and singer were also romantically engaged after being photographed together in Whole Foods wearing color-coordinated outfits in March 2015.
Taylor and Harris began dating when she was 26, and he was 31. They made their relationship public in the spring after Taylor posted a poolside bikini picture, with Harris later tweeting to praise her influence on the music industry.
They continued to post affectionate Instagram photos and supportive messages on Twitter about their relationship, occasionally discussing it openly. “It’s going really well,” Harris, known as Adam Wiles, mentioned to Kiss FM UK in July.
Following their one-year anniversary trip in April, Swift told Vogue, “I’m just going with the flow. I’m in a wonderful relationship right now. And I prefer to keep it private and low-key… This is the one aspect of my personal life that’s just for me.”
However, the magic faded, and by June 1, Swift and Harris had split. According to People magazine, the breakup wasn’t triggered by a specific event. “There was no drama,” a source shared with the magazine. “Sometimes things just don’t work out.”
- Tom Hiddleston
Taylor Swift had a relationship with Thomas William Hiddleston, known for his role as Loki in the Marvel Cinematic Universe.
Their connection began when they met and danced together at the Met Gala in 2016. Not long after, photos emerged of them kissing at a Rhode Island beach, confirming their relationship.
Their romance was brief, and they parted ways after a few months, with Taylor being 27 years old while Tom was 35 at the time of their breakup.
Rumors suggest that Swift wrote the song “Getaway Car” to express her remorse over quickly entering a new relationship following her breakup with Harris.
- Joe Alwyn
After ending her relationship with Tom Hiddleston, Taylor Swift began dating English actor Joe Alwyn. They crossed paths at the 2016 Met Gala and commenced their relationship a few months later. Despite keeping their romance low-key initially, news of their connection emerged the following year.
At the point they started dating Taylor was 27 while Joe was 25, in her 2020 autobiographical documentary, “Miss Americana,” Swift expressed her feelings, stating, “I was falling in love with someone who led a wonderfully normal, balanced life.” She emphasized their mutual decision to keep their relationship private, finding happiness in a way that didn’t rely on external validation.
However, the couple parted ways in April 2023 after being together for over six years.
- Matty Healy
Following her breakup with Alwyn, Swift was quickly linked romantically to The 1975 frontman Matty Healy; at this point, Taylor and Matty were both 34 years old.
A source told the Sun in May 2023 that despite being in the early stages of dating, both singers were deeply infatuated with each other. Amidst touring, they kept in touch through FaceTime and texts, eagerly anticipating their next meeting, with Healy supposedly planning to attend Swift’s Eras Tour stop in Nashville.
This wasn’t the first time Swift and Healy had sparked dating rumors; in late 2014, they were seen wearing each other’s merchandise. Healy initially mentioned they exchanged numbers but later clarified that their relationship was entirely fabricated.
However, just a month after their romance was made public, TMZ reported that they had already separated.
- Travis Kelce
In July 2023, during Swift’s Kansas City Eras Tour stop, NFL star Travis Kelce made a move but didn’t succeed.
However, two months later, reports surfaced that the Chiefs tight end was casually spending time with Swift. Jason Kelce, Travis’s brother and Eagles center, jokingly confirmed the dating rumors as “100 percent true,” although he admitted he wasn’t entirely in the loop about their relationship.
Their status became clearer when Swift attended the Kansas City Chiefs game on Sept. 24, sitting next to Travis’s mother in a suite and enthusiastically supporting the tight end during the match.
When they started dating, Taylor and Travis were both aged 34, and the two seemed to be having a great time enjoying each other’s company.