Taylor Swift has dated a variety of men, ranging from British crooner to a Kennedy, an Avengers villain, and even a movie werewolf. Among her notable partners are Harry Styles and Joe Jonas, as well as lesser-known individuals such as Conor Kennedy and actor Lucas Till. Each of these relationships has had a profound impact on the singer, inspiring several of her popular songs.
Reflecting on the first three decades of her life, Swift wrote an essay for ELLE in March 2019, where she shared her top life lessons, many of which revolved around her experiences in love.
In the essay, she emphasized the importance of getting to know someone before fully committing. Swift cautioned readers that appearances can be deceiving and initial impressions should not be relied upon entirely. She explained that while it may be impressive to witness someone effortlessly captivating a room, she now values the intricacies and depths of a person that unfold over time, rather than their initial charm. Swift referred to this initial charm as the "solid first 15" of a person's persona.
Scroll down to see what Swift's ex-boyfriends have been up to since they broke up with her:
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Taylor Swift's Exes: What the Singer's Former Flames Are Doing Now
Taylor Swift’s relationship history is made up of many different types of men, including a British crooner, a Kennedy, an Avengers villain and a movie werewolf.
Swift has been romantically connected to well-known celebrities like Harry Styles and Joe Jonas, as well as lesser-known individuals such as Conor Kennedy and actor Lucas Till. These past relationships have greatly influenced the singer and have often become the subjects of her popular songs. In March 2019, Swift took the time to reflect on the first 30 years of her life and shared her top life lessons in an essay for ELLE, many of which were derived from her experiences in love.
"Before diving in headfirst, perhaps it would be wise to get to know someone first! Not everything that shines is truly valuable, and initial impressions are not always the whole truth," she expressed. "It is indeed impressive when someone can immediately charm others and command attention, but what I now appreciate more in a person is not just their charismatic facade upon first meeting (which I refer to as a 'solid first 15'), but the intricate layers of their personality that unravel over time."
While the "Blank Space" singer may have declared that she will never reunite with Styles, Kennedy, Tom Hiddleston, or Taylor Lautner, her devoted fans, known as Swifties, are certainly keeping tabs on the post-breakup activities of her former flames.
Scroll down to see what Swift's exes have been doing since they parted ways:
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Joe Jonas
After a now-famous 27-second phone call in 2008, Jonas ended his relationship with Swift. He then dated a series of high-profile women including Camilla Belle, Demi Lovato, Ashley Greene, Blanda Eggenschwiler, and Gigi Hadid before finding love with Sophie Turner in October 2016. The singer and the Game of Thrones star got married in May 2019 and welcomed their first child, Willa, in July 2020. In March 2022, it was confirmed that they were expecting their second baby, and in July 2022, their second baby girl was born. However, after four years of marriage, Jonas filed for divorce in September 2023.
Following his role as Joe Lucas on Jonas, the musician released his debut solo album, Fastlife, in 2011. He then formed the band DNCE and released their self-titled debut album, DNCE, in 2016. In 2019, Jonas reunited with his brothers, Nick Jonas and Kevin Jonas, to bring back the Jonas Brothers. Since then, they have released Happiness Begins and The Album.
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Taylor Lautner
After his brief relationship with Swift in 2009, Lautner began dating Lily Collins, his co-star from the movie "Abduction" in 2010. However, they broke up in September 2011. Following this, the actor started a relationship with Marie Avgeropoulos in the summer of 2013, but they went their separate ways in January 2015. Lautner then had a romantic involvement with Billie Lourd for several months before their split in July 2017.
In October 2018, Lautner made his relationship with nurse girlfriend Taylor Dome official on Instagram. The couple surprised their fans by announcing their engagement in November 2021. Exactly one year later, they exchanged vows in a winery located in California.
After parting ways with Swift, the actor from Michigan, Taylor Lautner, has experienced ongoing achievements in his acting career. Notably, he portrayed Jacob Black in the renowned Twilight Saga films, earning significant recognition. Additionally, he showcased his talent in movies such as Grown Ups 2, Tracers, and Run the Tide. Lautner's versatility was showcased as he took on the role of Dr. Cassidy Cascade in Scream Queens and later portrayed Dale in Cuckoo. Interestingly, Lautner and Swift reunited on screen in July 2023 for the music video "I Can See You," featured on Speak Now (Taylor's Version).
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Lucas Till
In 2009, Till had a short-lived romantic involvement with the musician, which commenced after he appeared in her "You Belong With Me" music video. Subsequently, the actor from "Hannah Montana: The Movie" became associated with Debby Ryan before entering a relationship with Kayslee Collins from 2010 to 2012. His most recent romantic endeavor was with actress Carlson Young, however, their relationship ended in 2015 after three years together.
The talented Texan artist's professional journey has skyrocketed after his collaboration with the renowned "Red" singer in a mesmerizing music video performance. Till has showcased his acting prowess in a series of hit movies including The Spy Next Door, Crush, Paranoia, Dark Harts, and Bravetown. Moreover, he has portrayed the character of Alex Summers/Havok in three X-Men films, leaving a lasting impression on audiences. Notably, from 2016 to 2021, he captivated viewers as Angus MacGyver in the popular television series MacGyver.
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Jake Gyllenhaal
In January 2011, an exclusive source revealed that Swift was deeply upset when Gyllenhaal ended their two-month relationship before New Year's in 2010. Following their split, Gyllenhaal was seen with Jessica Lowndes in April 2011 and briefly involved with Minka Kelly in June 2012. Confirming this, Us reported in December 2018 that the Nightcrawler actor had been dating French model Jeanne Cadieu for the preceding six months.
During the past decade, the Oscar nominee has remained busy working on numerous films including 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
In January 2010, the pair sparked speculation about their relationship when they were seen having a two-hour dinner together at Nashville Bistro Cabana. Although their romance was short-lived, spanning from 2009 to 2010, Mayer still faces criticism from Swifties who relentlessly troll him for their breakup. Following that, the “Night Light” singer dated Katy Perry from 2012 to 2014.
Since his brief relationship with Swift, the talented artist from Connecticut has managed to maintain a successful career with no disruptions. In fact, he has even released four albums, including the recent Sob Rock in 2021. Additionally, he regularly tours with Dead & Company, a band formed by former members of the iconic Grateful Dead.
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Chord Overstreet
The Glee star, Overstreet, was romantically linked to Swift in February 2011 after their joint attendance at an L.A. Kings hockey game. It was reported that Overstreet showed interest in Swift, but their relationship did not progress further. Following their split, Overstreet went on to date Emma Roberts for almost a year before their breakup in January 2012. Subsequently, he had romantic involvements with Ashley Benson, Halston Sage, and Brooke Butler, until he began dating Emma Watson for six months in 2018. He was also linked to model Amanda Pizziconi from 2019 to 2020 before eventually starting a relationship with Camelia Somers in 2021.
In addition to his appearances on Pickle and Peanut and one episode of The Bold Type, Overstreet starred in the films 4th Man Out and The Swing of Things. He has also released three EPs: Tree House Tapes in 2017, Hold On in 2020, and Stone Man in 2021.
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Conor Kennedy
Swift had a summer fling with Robert F. Kennedy's grandson back in 2012. They were caught engaging in public displays of affection in Massachusetts for several months before ultimately ending their relationship in September of that year. Nearly ten years later, Conor was seen attending a Hamptons party with his model girlfriend, Ava Dash, in June 2021. Following that, he started dating the Brazilian singer, Giulia Be, in 2022.
Conor gained significant attention in December 2016 when he was apprehended in Aspen following an altercation at a bar. In February 2017, he accepted responsibility for disorderly conduct and justified his actions by stating that he was defending a friend who had been subjected to a homophobic slur. As part of his penalty, Conor paid a $500 fine, composed an apology letter to the victim, and was mandated to refrain from using drugs and alcohol for a period of six months. It is worth mentioning that Conor is also recognized for his involvement with the Ocean Alliance.
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Harry Styles
The One Direction singer and the songwriter of "Bad Blood" were seen together at the Central Park Zoo in December 2012. However, their relationship was short-lived as they went their separate ways in early 2013. Despite this, they showed that they are still on good terms when they attended the 2021 Grammys in March and were seen supporting each other at the event.
In 2013, Styles was linked to Kendall Jenner and they sparked rumors of a reconciliation two years later when they were seen on a yacht in Anguilla. From 2014 to 2015, there were rumors that the "Sweet Creature" singer was dating model Nadine Leopold. It was confirmed in May 2017 that Styles was casually seeing Tess Ward before being in a relationship with Camille Rowe for a year.
The musician, Harry Styles, began dating Olivia Wilde, his director in the film "Don't Worry Darling," in January 2021. In November 2022, it was confirmed that they had split and decided to take a break after being together for almost two years. Later, in June 2023, Styles moved on and started a relationship with actress Taylor Russell.
Styles, a British singer, released his first solo album, titled "Harry Styles," in 2017, following the split of the band One Direction the year before. He then released "Fine Line" in 2019, which earned him his first Grammy for Best Solo Pop Performance with the hit song "Watermelon Sugar" in 2021. In May 2022, Styles dropped his album "Harry's House." Apart from his music career, Styles has also ventured into acting, starting with his role in the 2017 film "Dunkirk." He later appeared in films such as "My Policeman" and "Don't Worry Darling." In 2023, Styles earned his second Grammy for Best Pop Vocal Album.
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Matt Healy
Swift's involvement with the 1975 guitarist was first revealed by us in late 2014. Following their time together, the "Robbers" musician went on to have brief relationships with Halsey in 2015 and Gabriella Brooks from 2015 to 2019. In February 2020, there were rumors of him dating FKA Twigs after Healy posted a cozy photo of them on social media. Throughout the years, the musician continued to release multiple records with his band, The 1975, with their latest release being 2020's Notes on a Conditional Form.
Healy and Swift's romantic connection resurfaced in May 2023, giving rise to criticism due to Healy's previous contentious remarks, which included mocking rapper Ice Spice's heritage. Following this, Swift released a revamped version of her track "Karma," featuring Ice Spice, during the same month before ultimately parting ways with Healy in June.
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Calvin Harris
The Scottish DJ, Calvin Harris, and singer Taylor Swift were in a relationship for 15 months before breaking up in June 2016. Afterwards, Harris reunited with model Aarika Wolf in August 2017, but their relationship didn't last long. However, they reconciled again in March 2018 and made a public appearance together at the 2019 BRIT Awards one year later. Unfortunately, they ultimately ended their relationship in March 2022, and Harris began dating Vick Hope later that same year. According to reports, Harris and Hope got married in September 2023.
As for his music career, Harris released his album Motion in 2014, followed by Funk Wav Bounces Vol. 1 in 2017. In April 2018, he collaborated with Dua Lipa on the hit song "One Kiss," and seven months later, he released "I Found You" with Benny Blanco. Under his Regenerator alias, Harris released three EPs in 2020. Then, in August 2022, he dropped Funk Wav Bounces Vol. 2.
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Tom Hiddleston
In 2016, The Avengers actor had a three-month relationship with Swift before she ended it. According to a close source, Swift was the one who decided to end the relationship because she was not comfortable with making it more public as Hiddleston wanted.
In 2020, Hiddleston was romantically linked to Betrayal costar Zawe Ashton. The Sun reported in July that they were living together in Atlanta, Georgia. In March 2022, it was confirmed by Us that the actors are engaged. The couple announced in June 2022 that they are expecting their first child. Four months later, Us confirmed that the baby had quietly arrived, with Hiddleston and Ashton becoming parents.
Shortly after his relationship with Swift ended, Hiddleston took on the role of Jonathan Pine in The Night Manager. He then went on to star in Kong: Skull Island, Thor: Ragnarok, and reprised his role as Loki in both Avengers: Infinity War and Avengers: Endgame. In 2021, his series Loki premiered, and it was renewed for a second season in 2023. Hiddleston also made an appearance in The Essex Serpent.
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Joe Alwyn
Swift and the actor from Conversations With Friends were first romantically linked in May 2017 and remained in a relationship for six years. During their time together, Alwyn co-wrote multiple songs with Swift for her albums Folklore and Evermore, including the track "Sweet Nothing" from the upcoming album Midnights in 2023. By being credited as a songwriter under the name William Bowery on Folklore, Alwyn received a Grammy for Album of the Year.
Following their breakup in April 2023, Alwyn is set to make a comeback to the film industry with various projects. He is expected to star opposite Riz Ahmed in a modern adaptation of Hamlet, and he will also appear in the movie And alongside Emma Stone, Jesse Plemons, Willem Dafoe, Margaret Qualley, and Hong Chau.