From Taylor Lautner to Jake Gyllenhaal to Harry Styles to Conor Kennedy and more!
Taylor Swift writes a lot about romance and relationships in her music but she doesn’t always have the nicest things to say about her former flames.
Despite sometimes throwing a little shade at her exes in her songs, Taylor is actually on good terms with a lot of them! She recently made headlines thanks to her tight knit relationship with her ex Taylor Lautner, whom she dated back in 2009. Besides being the subject of her apologetic song “Back to December,” Taylor recently asked him to star in her “I Can See You” music video — and called him one of her closest friends.
Read on to find out how Taylor feels about her exes…
Taylor was most recently linked to The 1975 frontman Matty Healy in May 2023. Matty was spotted at several Eras Tour shows and was even photographed holding hands with Taylor but in early June, news surfaced that the pair had split. Neither Taylor nor Matty have spoken out about the romance but sources tell People that the former couple aren’t in contact anymore.
“They were never boyfriend-girlfriend or exclusive and were always just having fun,” another insider shared. “There is no drama, and who knows what could happen again. It was a good time and ran its course.”
Taylor may have dated Joe Alwyn for over six years but the couple chose to keep things incredibly private. The pair didn’t even confirm their split when news surfaced that they had broken up in early 2023. While it was initially reported that the split was “not dramatic,” it seems as though there may have been some drama behind the scenes.
Not only did Taylor stop performing her love song “Invisible String” in concert in favor of the more melancholy “The 1,” almost all of her closest friends unfollowed Joe on social media. Some fans even believe Taylor’s Midnights vault track, “You’re Losing Me,” is about her split from Joe. Although Taylor hasn’t spoken out herself, fans believe her actions have shown that she’s not on good terms with Joe.
Taylor had a whirlwind relationship with Tom Hiddleston, dating him for three months in 2016. Their relationship ended just as suddenly as it began and while they never shared what went wrong, Tom has had nothing but kind things to say about Taylor.
“Taylor is an amazing woman. She’s generous and kind and lovely, and we had the best time,” he told GQ in 2017, adding, “Of course it was real.”
While the pair seem to be on good terms, Tom admitted that the split was difficult for him, especially with all the media attention surrounding their relationship. Looking back, he says the former couple just wanted a regular relationship.
“A relationship exists between two people. We will always know what it was. The narratives that are out there altogether have been extrapolated from pictures that were taken without consent or permission, with no context,” he said. “A relationship in the limelight…A relationship always takes work. A relationship in the limelight takes work. And it’s not just the limelight. It’s everything else.”
Calvin Harris dated Taylor for a little over a year, from 2015 to 2016. While their relationship was mostly kept on the down low, their breakup was highly publicized and very dramatic. While Calvin originally tweeted that there was still a “huge amount of love and respect” between them, things changed when it was revealed that Taylor had secretly written Calvin’s song “This Is What You Came For” under a pseudonym.
It was reported that while the couple were still dating, Calvin gave an interview about the song where he said he couldn’t foresee ever working with Taylor — despite the fact that she had a large role in writing the song. The report painted Calvin in a negative light, causing him to go off on Twitter, even referencing Taylor’s new relationship with Tom Hiddleston.
“Hurtful to me at this point that her and her team would go so far out of their way to try and make ME look bad at this stage…I figure if you’re happy in your new relationship you should focus on that instead of trying to tear your ex bf down for something to do. I know you’re off tour and you need someone new to try and bury like Katy [Perry] ETC but I’m not that guy, sorry. I won’t allow it,” Harris wrote in now-deleted tweets. “Please focus on the positive aspects of YOUR life because you’ve earned a great one.”
While Calvin seemed angry at the time, he later admitted that he regretted his Twitter rant about Taylor.
“When it ended, all hell broke loose. Now I see that Twitter thing as a result of me succumbing to pressure. It took me a minute to realize that none of that matters. I’m a positive guy. For both of us, it was the wrong situation. It clearly wasn’t right, so it ended, but all of the stuff that happened afterwards,” Calvin told British GQ in September 2016.
In 2017, the magazine shared some of Calvin’s additional comments from the interview where he said the Twitter situation was “completely the wrong instinct” and an attempt at “protecting” what he sees as his “one talent in the world being belittled.”
Taylor dated Harry Styles for just a few months — from October 2012 to January 2013. In the wake of their split, there was a lot of speculation and quite a few songs written about each other. Despite parting ways, Taylor and Harry have appeared to remain cordial through the years. In 2017, Harry even looked back on their relationship, speaking out about the iconic photos of the pair walking through Central Park.
“When I see photos from that day, I think: Relationships are hard, at any age. And adding in that you don’t really understand exactly how it works when you’re 18, trying to navigate all that stuff didn’t make it easier. I mean, you’re a little bit awkward to begin with. You’re on a date with someone you really like. It should be that simple, right? It was a learning experience for sure. But at the heart of it — I just wanted it to be a normal date,” he told Rolling Stone.
He later added, “Certain things don’t work out. There’s a lot of things that can be right, and it’s still wrong. In writing songs about stuff like that, I like tipping a hat to the time together. You’re celebrating the fact it was powerful and made you feel something, rather than ‘this didn’t work out, and that’s bad.’ And if you run into that person, maybe it’s awkward, maybe you have to get drunk…but you shared something. Meeting someone new, sharing those experiences, it’s the best s–t ever. So thank you.”
The pair even briefly reunited at both the 2021 and 2023 Grammys, where they could be seen having friendly chats.
In 2012, Taylor briefly dated Robert F. Kennedy’s grandson, Conor Kennedy. The couple spent the summer at the Kennedy compound in Hyannis Port, Massachusetts — and Taylor purchased a home nearby soon after. After some controversy surrounding their age difference and their attendance at a wedding they reportedly weren’t invited to, the couple called it quits.
Taylor and Conor have never spoken out about their summer romance, although some of the songs on Red were rumored to be about their relationship. While talking about her dating life shortly after their split, Taylor admitted she struggled to date in the public eye.
“I don’t know how to have a normal relationship because I try to act normal, love from a normal place and live a normal life, but there is sort of an abnormal magnifying glass, like telescope lens, on everything that happens between me and anybody else,” she said. “I don’t really know that much about love, it turns out.”
In late 2010, Taylor began dating Jake Gyllenhaal. The couple dated for a few months, splitting in early 2011. Following their breakup, Jake became the subject of rumors that some songs on Taylor’s Red were about him. The pair were both tight-lipped for years but their relationship made headlines once again when Taylor released a 10-minute version of her song “All Too Well.”
“It was a day when I was just, like, a broken human, walking into rehearsal just feeling terrible about what was going on in my personal life,” she explained on Rolling Stone’s 500 Greatest Albums podcast.
Along with the full song, which was long speculated to be about Jake, Taylor also released a short film starring Sadie Sink and Dylan O’Brien — whose ages line up with how old Taylor and Jake were during their relationship. The video depicted a toxic relationship, which many fans speculated reflected how Jake treated Taylor.
In the wake of the song’s release, Jake was once again asked about the pair’s relationship. He took the opportunity to call out Taylor’s fans for bullying him online.
“At some point, I think it’s important when supporters get unruly that we feel a responsibility to have them be civil and not allow for cyberbullying in one’s name,” he told Esquire. “That begs for a deeper philosophical question. Not about any individual, per se, but a conversation that allows us to examine how we can — or should, even — take responsibility for what we put into the world, our contributions into the world. How do we provoke a conversation? We see that in politics. There’s anger and divisiveness, and it’s literally life-threatening in the extreme.”
As for the song, he said, “It is her expression. Artists tap into personal experiences for inspiration, and I don’t begrudge anyone that.”
Taylor was linked with John Mayer from late 2009 to early 2010.
While she is not one to name drop in her songs, she was very pointed in her release of “Dear John.” On the track, Taylor commented, “Don’t you think I was too young to be messed with? The girl in the dress cried the whole way home.”
Looking back a few years later, John said he had no warning the song was going to be released and it made him “feel terrible.”
“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,” he told Rolling Stone. “I never got an email. I never got a phone call. I was really caught off-guard, and it really humiliated me at a time when I’d already been dressed down. I mean, how would you feel if, at the lowest you’ve ever been, someone kicked you even lower?”
Through the years, the former couple’s relationship has seemed to improve, with John even calling Taylor’s album “a fine piece of work.” Then, ahead of the rerelease of “Speak Now,” Taylor asked fans to be kind to those she’s written songs about, seemingly referencing John.
“I’m 33 years old. I don’t care about anything that happened to me when I was 19,” she said. “I was hoping to ask you, that as we lead up to this album, I would love for that kindness and that gentleness to extend onto our Internet activities. Right? I’m not putting this album out so you can go on the Internet and defend me against someone you think I wrote a song about 14 million years ago. I do not care, we have all grown up, we’re good.”
Taylor may have only dated Taylor Lautner from October to December 2009, but he’s become a favorite among fans. He even inspired Taylor’s song “Back to December,” where she looks back fondly on their relationship and offers an apology for ending things. Through the years, “the Taylors” have remained on good terms and she even asked him to appear in her music video for “I Can See You” — a vault track from the Speak Now rerelease. On the night of the video’s premiere, Taylor had the other Taylor join her on stage at her Eras Tour date.
“He was a very positive force in my life when I was making the Speak Now album and I want to say he did every single stunt that you saw in that music video,” she said on stage. “He and his wife have become some of my closest friends and it’s very convenient because we all share the same first name.”
In response, he called his ex “gracious, humble, kind” and said he was “honored” to know her.
Taylor was briefly linked to Lucas Till in 2009 after he co-starred in her “You Belong With Me” music video. While Taylor hasn’t spoken out about their short relationship, things ended on good terms according to Lucas.
“We dated for a little bit. But there was no friction because we were too nice,” he told MTV in 2009. “We just really both liked each other…[but] most relationships work out ’cause you get along and then you don’t, and then you make up and it’s passionate, and with us, I really just liked her as a friend. That’s the only reason that didn’t work out.”
Taylor dated Joe Jonas from July to October 2008 and she infamously called him out on The Ellen Degeneres Show after they broke up during a 25-second phone call. While there were definitely some hard feelings at the time, Taylor says things are all good between the pair now — and she regrets causing drama.
“I put Joe Jonas on blast on your show. That was too much, that was too much. I was 18…We laugh about it now, but that was mouthy, yeah, some teenage stuff there,” she said during a 2019 appearance on the talk show.
In response, Joe said it felt “nice” to hear her apology, saying, “It’s something that I was probably feeling pretty bad about when I was younger, but, at the end of the day, I’ve moved on. I’m sure Taylor’s moved on. It feels nice. We’re all friends. It’s all good. We were so young.”