Magic, madness, heaven, sin! Taylor Swift’s relationship history is made up of many different types of men, including a British crooner, a Kennedy, an Avenger and a movie werewolf.
Swift has been linked to massive stars, such as Harry Styles and Joe Jonas, in addition to lesser-known names like Conor Kennedy and a then-up-and-coming actor Lucas Till. All of her past relationships have shaped the singer, and many have wound up being topics in her hit tracks.
Seven years after their whirlwind romance, Styles revealed why some relationships end and what he learned from Swift during their time together.
“Certain things don’t work out. There’s a lot of things that can be right, and it’s still wrong,” the “Golden” crooner told Rolling Stone in April 2017. “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.”
Styles noted that the problem with Swift potentially writing songs about her former beaus — “Out of the Woods” and “Style” are rumored to be about the English musician — is that “she’s so good, they’re bloody everywhere.”
The “Perfect” singer added that he’s “lucky” if their time together “helped create those songs,” calling Swift’s work “the most amazing unspoken dialogue ever.
The “22” singer, for her part, reflected on the first 30 years of her life, penning an essay for ELLE in March 2019 about her top life lessons thus far, many of which pointed to her love life.
“Before you jump in headfirst, maybe, I don’t know … get to know someone! All that glitters isn’t gold, and first impressions actually aren’t everything,” she wrote at the time. “It’s impressive when someone can charm people instantly and own the room, but what I know now to be more valuable about a person is not their charming routine upon meeting them (I call it a ‘solid first 15’), but the layers of a person you discover in time.”
The “Blank Space” songstress may have said she’s never getting back together with Styles, Kennedy, Tom Hiddleston or Taylor Lautner, but that doesn’t mean Swifties aren’t keeping up with what her former flames have been up to since their high-profile splits.
Scroll down to see what Swift’s exes have been doing since they parted ways:
Magic, madness, heaven, sin! Taylor Swift’s relationship history is made up of many different types of men, including a British crooner, a Kennedy, an Avenger and a movie werewolf.
Swift has been linked to massive stars, such as Harry Styles and Joe Jonas, in addition to lesser-known names like Conor Kennedy and a then-up-and-coming actor Lucas Till. All of her past relationships have shaped the singer, and many have wound up being topics in her hit tracks.
Seven years after their whirlwind romance, Styles revealed why some relationships end and what he learned from Swift during their time together.
“Certain things don’t work out. There’s a lot of things that can be right, and it’s still wrong,” the “Golden” crooner told Rolling Stone in April 2017. “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.”
Styles noted that the problem with Swift potentially writing songs about her former beaus — “Out of the Woods” and “Style” are rumored to be about the English musician — is that “she’s so good, they’re bloody everywhere.”
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The “Perfect” singer added that he’s “lucky” if their time together “helped create those songs,” calling Swift’s work “the most amazing unspoken dialogue ever.
The “22” singer, for her part, reflected on the first 30 years of her life, penning an essay for ELLE in March 2019 about her top life lessons thus far, many of which pointed to her love life.
“Before you jump in headfirst, maybe, I don’t know … get to know someone! All that glitters isn’t gold, and first impressions actually aren’t everything,” she wrote at the time. “It’s impressive when someone can charm people instantly and own the room, but what I know now to be more valuable about a person is not their charming routine upon meeting them (I call it a ‘solid first 15’), but the layers of a person you discover in time.”
The “Blank Space” songstress may have said she’s never getting back together with Styles, Kennedy, Tom Hiddleston or Taylor Lautner, but that doesn’t mean Swifties aren’t keeping up with what her former flames have been up to since their high-profile splits.
Scroll down to see what Swift’s exes have been doing since they parted ways:
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Joe Jonas
The former Disney Channel star ended his relationship with Swift in a now-famous 27-second phone call in 2008. He went on to date Camilla Belle, Demi Lovato, Ashley Greene and Gigi Hadid before finding love with Sophie Turner in October 2016. The singer and the Game of Thrones alum tied the knot in May 2019 and welcomed their first child, Willa, in July 2020. Us confirmed in March 2022 that the duo were expecting baby No. 2. Their second baby girl arrived in July 2022.
Following his role as Joe Lucas on Jonas, the musician released his first solo album, Fastlife, in 2011. He then created the group DNCE and dropped the band’s first album, DNCE, in 2016. Jonas reunited with his brothers, Nick Jonas and Kevin Jonas, in 2019 to bring back the Jonas Brothers. They have since released the album Happiness Begins.
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Taylor Lautner
Following his three-month romance with Swift in 2009, Lautner moved on with his Abduction costar Lily Collins after meeting on the 2010 movie set. The pair split in September 2011. The actor started dating Marie Avgeropoulos in the summer of 2013, but the duo went their separate ways in January 2015. Lautner then dated Billie Lourd for several months before splitting in July 2017.
He became Instagram official with nurse girlfriend Taylor Dome in October 2018. The couple announced their engagement in November 2021. The duo said “I do” exactly one year later at a winery in California.
The Michigan native has continued to find success in acting since splitting from Swift, playing Jacob Black in five Twilight Saga films. He also starred in Grown Ups 2, Tracers and Run the Tide. The actor played Dr. Cassidy Cascade on Scream Queens before portraying Dale on Cuckoo.
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Lucas Till
Till had a brief romance with the musician in 2009 after he starred in her “You Belong With Me” music video in 2009. The Hannah Montana: The Movie actor was then linked to Debby Ryan before dating Kayslee Collins from 2010 to 2012. He was most recently in a relationship with actress Carlson Young, but things fizzled out in 2015 after three years together.
The Texas native’s career has taken off since his music video performance alongside the “Red” singer. Till starred in The Spy Next Door, Crush, Paranoia, Dark Harts, Bravetown and played Alex Summers/Havok in three X-Men films. He has been playing Angus MacGyver on MacGyver since 2016.
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Jake Gyllenhaal
A source exclusively told Us Weekly in January 2011 that Swift was “really upset” after Gyllenhaal broke off their two-month romance ahead of New Year’s in 2010. More than a decade later, some fans think Swift’s “Mr. Perfectly Fine,” which was an April 2021 vault release, was written about the actor after their split. Months after their breakup, Gyllenhaal was spotted with Jessica Lowndes in April 2011 before having a brief fling with Minka Kelly in June 2012. Us confirmed in December 2018 that the Nightcrawler actor had begun seeing French model Jeanne Cadieu six months prior.
The Oscar nominee has kept himself busy, working on a number of films over the past decade. He starred in End of Watch, Enemy, Southpaw, Everest, Demolition, Nocturnal Animals, Spider-Man: Far From Home, The Guilty and The Division.
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John Mayer
The pair caused relationship speculation in January 2010 after they were spotted at a two-hour dinner together at Nashville Bistro Cabana. Although their romance was brief, from 2009 to 2010, Mayer has continued to get heat from Swifties who can’t stop trolling him for their breakup. The “Night Light” singer then dated Katy Perry from 2012 to 2014.
The Connecticut native hasn’t let breakups and makeups slow down his career, releasing four albums, including 2021’s Sob Rock since his hookup with Swift.
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Chord Overstreet
The Glee star was linked to the “Lover” singer in February 2011 after they attended an L.A. Kings hockey game together. A source told Us at the time that the actor was “into” Swift, but the romance didn’t go anywhere. Overstreet moved on with Emma Roberts, whom he dated for nearly one year before calling it quits in January 2012. He later romanced Ashley Benson, Halston Sage and Brooke Butler before dating Emma Watson for six months in 2018. He was linked to model Amanda Pizziconi from 2019 to 2020.
The Tennessee native starred in 4th Man Out and The Swing of Things in addition to appearing on Pickle and Peanut and one episode of The Bold Type. Overstreet has also released three EPs, 2017’s Tree House Tapes, 2020’s Hold On and 2021’s Stone Man.
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Conor Kennedy
Robert F. Kennedy’s grandson had a summer romance with the Miss Americana star in 2012. After packing on major PDA in Massachusetts for months, the pair called it quits that September. Nearly a decade later, Conor stepped out with model girlfriend Ava Dash at a Hamptons party in June 2021.
Conor made headlines in December 2016 when he was arrested in Aspen following a bar fight. He pleaded guilty in February 2017 to disorderly conduct, claiming he was defending a friend who was called a homophobic slur. He paid a $500 fine and was ordered to write an apology letter to the victim and abstain from drugs and alcohol for six months. He is also known for his work with the Ocean Alliance.
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Harry Styles
The former One Direction singer and the “Bad Blood” songwriter were spotted together at the Central Park Zoo in December 2012. Their romance was short-lived, however, with the pair going their separate ways in early 2013. The former flames proved they are on good terms while attending the 2021 Grammys in March, as they were spotted supporting one another at the show.
Styles was linked to Kendall Jenner in 2013 and sparked reconciliation rumors two years later when they were spotted on a yacht in Anguilla. The “Sweet Creature” crooner was rumored to be dating model Nadine Leopold from 2014 to 2015. Us confirmed in May 2017 that Styles was “casually seeing” Tess Ward before romancing Camille Rowe for a year.
The musician started dating his Don’t Worry Darling director, Olivia Wilde, in January 2021. Us confirmed in November 2022 that the duo split and were taking a break after nearly two years together.
The British crooner dropped his first solo album, Harry Styles, in 2017, after One Direction split one year prior. He released Fine Line in 2019 and earned his first Grammy for Best Solo Pop Performance with “Watermelon Sugar” in 2021. The musician dropped Harry’s House in May 2022. Styles starred in 2017’s Dunkirk before landing roles in My Policeman and Don’t Worry Darling.
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Matt Healy
Us exclusively revealed that Swift spent time with the 1975 guitarist in late 2014. The “Robbers” rocker has since dated Halsey (briefly in 2015) and Gabriella Brooks from 2015 to 2019. He was rumored to be seeing FKA Twigs in February 2020 after Healy shared a photo of the pair getting cozy on social media. The musician released three records with his band 1975 following his brief fling with Swift, including 2020’s Notes on a Conditional Form.
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Calvin Harris
The Scottish DJ and the “Exile” singer dated for 15 months, splitting in June 2016. Harris rekindled his romance with model Aarika Wolf in August 2017, but quickly ended things. They got back together in March 2018, stepping out at the 2019 BRIT Awards one year later.
The musician released Motion in 2014 and Funk Wav Bounces Vol. 1 in 2017. He then dropped “One Kiss” with Dua Lipa in April 2018 and “I Found You” with Benny Blanco seven months later. He released three EPs in 2020 under his Regenerator alias.
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Tom Hiddleston
The Avengers actor dated Swift for three months in 2016 before the “Welcome to New York” singer broke it off. “She was the one to put the brakes on the relationship,” a source close to the couple told Us in September of that year. “Tom wanted the relationship to be more public than she was comfortable with.”
Hiddleston was linked to Betrayal costar Zawe Ashton in 2020, with The Sun reporting in July that they were living together in Atlanta, Georgia. Us confirmed in March 2022 that the actors are engaged. The pair revealed in June 2022 that they were expecting their first child. Four months later, Us confirmed that the Marvel star and the England native quietly welcomed their baby.
Shortly after his romance with Swift fizzled out, Hiddleston played Jonathan Pine on The Night Manager. He then appeared in Kong: Skull Island, Thor: Ragnarok and portrayed Loki in both Avengers: Infinity War and Avengers: Endgame. His series Loki premiered in 2021 and Hiddleston is currently filming the miniseries The Essex Serpent.
