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Calvin Harris (2015-2016)

Taylor Swift and Calvin Harris met socially in February 2015 at the Elle Style Awards in London, UK. The couple dated from March 2015-May 2016, and despite the initially breakup being amicable the pair later turned publicly against each other. Swift is believed to have written multiple songs for Harris, including This Is What You Came For & I Did Something Bad.

In late March 2015, the couple were photographed with fans while shopping at Whole Foods in Nashville TN while wearing coordinated outfits.

In April 2015, Swift and Harris were again photographed in coordinated outfits at a Haim concert in Los Angeles CA.

Several weeks later, Harris made their relationship Instagram official by posting a picture of Swift’s cats, Meredith and Olivia, to his page.

In May 2015, despite walking the red carpet separately, Swift and Harris were seated next to each other at the Billboard Music Awards in Las Vegas NV.

Weeks later, Swift and Harris were photographed holding hands while walking to and from her apartment in TriBeCa NY.

In June 2015, it was Swift’s turn to make their relationship Instagram official by posting a picture of herself with Harris riding a giant inflatable swan in a pool.

Weeks later, while in London UK for Swift’s 1989 World Tour, Swift and Harris took a boat trip on the River Thames alongside artist Joe Jonas and models Gigi Hadid and Karlie Kloss.

In July 2015, the couple celebrated Fourth of July together at Swift’s historic mansion in Watch Hill RI.

In December 2015, Swift and Harris celebrated her 26th birthday with Swift’s family in Beverley Hills CA.

Ahead of Christmas, Swift shared pictures via Instagram of herself and Harris building snowmen with her younger brother, Austin Swift.

Days later, the couple celebrated the new year together at Club Omnia in Las Vegas NV where Harris was performing.

In January 2016, a fan date-crashed Swift and Harris while dining at Giorgio Baldi’s restaurant in Santa Monica CA, later posting an Instagram captioned “Date night with mom and dad”. Swift and Harris took it in good humour and even played into the hijinx.

In February 2016, Harris congratulated Swift on her phenomenal Grammys win with a celebratory Instagram post dedicated to his “beautiful girlfriend”.

In March 2016, the couple celebrated their one year anniversary by baking a heart shaped cake and a dinner date in Los Angeles CA in which Harris gifted Swift a custom engraved vintage locket.

Weeks later, the couple flew to an undisclosed private island to properly celebrate the milestone and enjoyed their first official holiday together.

In April 2016, Swift thanks Harris for his support during her iHeart Radio Awards acceptance speech, stating "For the first time I had the most amazing person to come home to when the spotlight went out and when the crowds were all gone," and referring to him by his real name, Adam Wiles.

Weeks later, Swift and Harris were photographed wearing matching custom leather jackets embroidered with the single artwork of Harris’ latest release, “This Is What You Came For (feat. Rihanna)”. The couple attended Coachella together where Swift supported his new work further, and even promoted it to her social medias.

In June 2016, People magazine confirmed Swift and Harris had quietly split several weeks earlier under amicable terms.

Harris stated in a tweet “The only truth is that a relationship came to an end & what remains is a huge amount of love and respect." and was retweeted by Swift.

Weeks later, Harris deleted all pictures of Swift from his social medias and his tweet confirming the breakup was amicable following photographs of Swift kissing British actor, Tom Hiddleston, on the beachfront of her Watch Hill RI home.

In July 2016, Harris erupted in an explosion of tweets suggesting Swift was only dating somebody new in an effort to hurt him out of boredom, stating “I know you’re off tour and you need someone new to try and bury like Katy ETC but I’m not that guy, sorry. I won’t allow it”

Swift responded by revealing it was herself who actually wrote Harris’ smash hit, “This Is What You Came For (feat. Rihanna)”, and in fact not himself.

In June 2017, Harris apologised for his behaviour following his breakup with Swift in an interview with GQ.

The couple are not known to have had contact since.

[taylorswiftexlovers]

Conor Kennedy (2012)

Taylor and Conor Kennedy met socially in July 2012 after his grandmother, Ethel Kennedy, invited Taylor to the family’s Fourth of July celebrations at the Kennedy compound in Hyannis Port MA. The couple dated from July-August 2012. Taylor has written one known song for Conor Kennedy - Everything Has Changed.

Over the Fourth of July, Taylor was photographed celebrating at the Kennedy compound waterfront property in Hyannis Port MA, and yachting with the entire extended Kennedy family.

In late July, Taylor was photographed walking along the harbour with Conor Kennedy and taking a yacht trip with his entire family.

The following day, Taylor and Conor Kennedy were photographed walking down the Cape Cod lane together.

In August, Taylor was photographed taking more yacht trips with the Kennedy family and visiting the Cape Cod beach together.

A week later, Taylor and Conor Kennedy were photographed eating at Pancake Pantry in Nashville TN with Taylor’s parents.

A week later, Taylor and Conor Kennedy were photographed back on the Cape Cod harbour and visiting the beach.

Over this weekend, they attended the wedding of Conor Kennedy’s cousin, Kyle Kennedy. According to Conor Kennedy’s aunt, Victoria Gifford-Kennedy, he had not RSVP’d to the wedding prior to attending, and had not mentioned Taylor being his addition. The couple were asked to leave after Victoria Gifford-Kennedy decided Taylor’s presence at the wedding would “distract from the bride”.

According to Paula Erikson, Taylor’s then-publicist, bride Kyle Kennedy profusely thanked Taylor for attending her wedding and that there was no truth to the “wedding crasher” headlines.

In the days following media confirmation of Taylor‘s presence in Cape Cod, fans began holidaying to the peninsula hopeful to meet her.

Taylor and Conor Kennedy were photographed walking through Cape Cod together for the rest of the month, and most notably visiting the grave of Conor Kennedy’s late mother, Mary Kennedy.

The couple’s split was confirmed in early September, citing “busy schedules” as the reason. Taylor and Conor Kennedy have not been known to have contact since.

[taylorswiftexlovers]

Harry Styles (2012-2013)

Taylor and Harry Styles met socially in March 2012 when Taylor visited One Direction’s dressing room backstage at the Kid’s Choice Awards. The couple briefly dated in April 2012, and again in September 2012-January 2013. Taylor has written multiple songs for Harry Styles, including Treacherous, Come Back... Be Here, Babe, I Knew You Were Trouble, This Love, How You Get The Girl, Wildest Dreams, I Know Places, Wonderland, Out of the Woods, Style, All You Had To Do Was Stay, I Wish You Would, and Clean.

In March 2012, Taylor attended the Kid’s Choice Awards in Los Angeles CA, where she met Harry Styles and the rest of his band, One Direction, backstage while their dressing room to introduce herself.

Taylor and Harry Styles began dating shortly after. One Direction travelled to Australiasia and New Zealand in April to tour.

Taylor and Harry Styles broke up by the end of April 2012 after paparazzi photos of Harry Styles kissing model, Emily Ostilly, while in New Zealand were published.

In 2013, Taylor later confirmed to Vanity Fair she had been initially intentionally misled by Harry Styles to believe that the paparazzi photos were of himself “saying goodbye to a friend”, however when Taylor viewed the pictures for herself she realised he was being untruthful and decided to end their relationship.

In October 2012, the couple rekindled their relationship as Taylor was sighted repeatedly wearing Harry Styles’ well-recognised paper airplane necklace - which was notably absent from Harry Styles’ person at this time.

In December 2012, Taylor and Harry Styles were photographed walking around Central Park in New York City NY together. Days later, the couple were photographed dining at the Crosby Hotel together in New York City NY.

Over Taylor’s 23rd birthday, the couple travelled to the Lake District in England. Days before Christmas, the couple flew back to the USA and holidayed at Canyons Resort skiing part in Park City UT with fellow artists Selena Gomez, Justin Bieber, and Taylor’s brother, Austin.

The couple rang in the New Year at Times Square in New York City NY where Taylor was performing, and were sighted kissing as the ball dropped.

https://youtu.be/M7RH8TAf4yY

Later in the day, the couple flew to Virgin Gorda in the British Virgin Islands and took pictures with fans at CocoMaya restaurant.

Several days later, Taylor was photographed leaving the island alone and later tweeted lyrics “‘Til you put me down.” from I Knew You Were Trouble. In 2013, she confirmed to Vanity Fair the reason behind their split as “trust issues”.

Harry Styles continued to holiday on neighbouring island, Necker Island, and partied alongside Richard Branson.

In August 2013, Taylor and Harry Styles were filmed texting each other from their nearby rows at the VMA Awards in Brooklyn NY. The former couple later took a picture together with their mutual friends.

In January 2015, Taylor and Harry Styles both attended the birthday party of Caleb Followill of Kings of Leon at the Sunset Marquis hotel in Los Angeles CA alongside mutual friends.

https://youtu.be/8ynbc9GvTzM

[taylorswiftexlovers]

Jake Gyllenhaal (2010)

Taylor and Jake Gyllenhaal met socially when both were invited to the dinner party of couple Gwyneth Paltrow and Chris Martin in September 2010. The couple dated from October-December 2010. Taylor has written multiple songs for Jake Gyllenhaal, including State of Grace, Red, The Moment I Knew, All Too Well, Better Man, Sad Beautiful Tragic, I Almost Do, The Last Time, and We Are Never Ever Getting Back Together.

In October 2010, Taylor and Jake Gyllenhaal were sighted apple picking together at Fishkill Farms in Hopewell Junction NY.

The following day, Taylor was invited by Emma Stone to her SNL taping in Manhattan NY, and brought Jake Gyllenhaal along with her.

The next morning, Taylor and Jake Gyllenhaal were sighted eating brunch together at Al Di La in Brooklyn NY, and later walking through Park Slope together.

Over Halloween, the couple holidayed at Post Ranch in Big Sur CA. They later took a road trip and were sighted at McConnell’s ice cream store in Santa Barbara; according to the staff "They looked at all the flavors and couldn't decide, so they asked the counter girls for help.”

In November 2010, the couple were sighted at Fido’s coffee store in Nashville TN on two separate occasions.

Jake Gyllenhaal spent Thanksgiving with Taylor’s family in Nashville TN.

In December 2010, the couple were photographed in Brooklyn NY alongside Jake Gyllenhaal’s sister, Maggie Gyllenhaal.

Days later, the couple were photographed driving around Los Angeles CA in a heated discussion.

Days later, Taylor celebrated her 21st birthday by throwing a house party at her parents’ home in Hendersonville TN, while Jake Gyllenhaal stayed in Los Angeles CA.

In January 2011, Us Weekly confirmed the couple had split days prior to New Year’s Eve, citing “age differences” as the cause for break up.

[taylorswiftexlovers]

John Mayer (2009-2010)

John Mayer and Taylor met while recording Half of My Heart for John Mayer’s album, Battle Studies. The couple dated from December 2009-February 2010. Taylor has written multiple songs for John Mayer, including Superman, Ours, Dear John, and The Story of Us.

Before John Mayer and Taylor ever met, John Mayer posted tweet "Waking up to this song idea that won't leave my head. 3 days straight now. That means it's good enough to finish.” & “It's called 'Half of My Heart' and I want to sing it with Taylor Swift. She would make a killer 'Nicks' in contrast to my 'Petty' of a song." in March 2009.

While being interviewed for Elle Magazine, Taylor responded "I freaked out when I heard, because I've been such a big fan of John for such a long time. I'm really excited about just the idea that he would even mention me in his Twitter!"

In May 2009, Taylor invited John Mayer to be the surprise guest on her Fearless Tour show in Los Angeles CA. Together, they performed “White Horse” and John Mayer’s song “Your Body Is A Wonderland”.

https://youtu.be/3ol9jTvYBhE

In June 2009, John Mayer released “Half of My Heart” with Taylor’s vocal feature.

In December 2009, Taylor was photographed having dinner in New York City with John Mayer.

A week later, Taylor and John Mayer performed “Half of My Heart” together at the New York City Z100 Jingle Bell Ball. After their set, they were sighted in the audience with Taylor sat on his knee with her arms around his neck.

https://youtu.be/U8k_Paf4E14

In January 2010, Taylor was photographed leaving the taping of John Mayer’s CMT Crossroads episode in Nashville, Tennessee.

The couple reportedly split in February 2010 with reasons uncited.

In June 2010, John Mayer made a surprise appearance at the CMT Awards where Taylor was also attending. Taylor was photographed walking to his row to speak to him. The night ended up being coded into the lyrics of The Story of Us.

Several days after the CMT Awards, John Mayer presented Taylor with her Hal David Starlight Award as she was inducted into the Songwriters’ Hall of Fame. During his presentation, he referred to Taylor and himself as “black swans”.

https://youtu.be/gTeW9AVpUAA

In October 2010, Taylor released her third studio album, Speak Now, directly naming him in the song “Dear John”.

In 2012, John Mayer told Rolling Stone magazine that he was “really humiliated” by the track and that it made him feel “terrible”. John Mayer withdrew his former compliments to Taylor’s artistry and labelled her songwriting as “cheap”.

In 2013, John Mayer released his song “Paper Doll” in response to the aftermath of his and Taylor’s relationship.

[taylorswiftexlovers]

Taylor Lautner (2009)

Taylor Lautner and Taylor met professionally while working alongside each other filming for Valentine’s Day in July-August 2009. The couple dated from September-December 2009, and although were not on good terms initially later reconciled. Taylor has written a song for Taylor Lautner, Back To December.

https://youtu.be/TWx9XGGWljc

Taylor and Taylor Lautner playing fictional high school couple, Felicia Miller and Willie Harrington.

In September 2009, Taylor Lautner comforted Taylor onstage during the infamous MTV VMA Awards as Kanye West stormed the stage and took her mic; this moment was later reference in Back To December through the lyric “And how you held me in your arms that September night, the first time you ever saw me cry.”

https://youtu.be/s0Urcv7vjlc

In October 2009, Taylor Lautner attended Taylor’s Fearless Tour in Chicago IL. After Fifteen, the pair hugged offstage.

Between October-December 2009, the pair were photographed meeting up in Chicago IL, at a hockey game in Los Angeles CA, shopping together in Beverley Hills CA, and getting frozen yogurt together in Beverley Hills CA.

https://youtu.be/W2twcSFYlt0

In November 2009, Taylor name dropped Taylor Lautner while performing her original monologue song on SNL.

In December 2009, the couple broke up with sources stating Taylor Lautner had liked Taylor Swift more than she had liked him, and ultimately the relationship wasn’t going anywhere.

In October 2010, Taylor Swift released Back To December with the message “TAY” coded into the lyric booklet. In the liner notes of her third studio album, Speak Now, Taylor described the song as a letter “to the beautiful boy whose heart I broke in December”.

Taylor Swift and Taylor Lautner have since made up and have been photographed together again at award shows in past years.

[taylorswiftexlovers]

Lucas Till (2009)

Lucas Till and Taylor met professionally while working alongside each other filming for Hannah Montana: The Movie in April-July 2008, while Taylor was then-dating American singer-songwriter, Joe Jonas. In spring 2009, Taylor cast Lucas Till as a love interest for her You Belong With Me music video. Taylor and Lucas dated for several weeks March-April 2009, before breaking up amicably after their feelings didn’t lead anywhere. Taylor has written no known songs for Lucas Till.

Mikey Cyrus, Lucas Till, and Taylor Swift filming onset for Hannah Montana: The Movie in 2008

https://youtu.be/vTJ1X7weUMQ

While filming for Taylor’s You Belong With Me music video in 2009, Lucas talks about how nervous he is to kiss Taylor during the prom scene, whereas Taylor reflects back on how self-conscious she felt kissing Lucas in front of a hall of actual high school students.

Taylor and Lucas took pictures with fans while on a date at a frozen yogurt bar in April 2009.

In 2010, Lucas spoke with Us Weekly on his and Taylor’s relationship, explaining “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.”

[taylorswiftexlovers]

Joe Jonas (2008)

Joe Jonas and Taylor met professionally whilst working alongside each other filming for Jonas Brothers: The 3D Concert Experience in 2008. Taylor and Joe dated for several months from the summer to the fall of 2008, before Joe suddenly broke off their relationship to date actress, Camilla Belle, instead. Taylor has written numerous songs for Joe, including Jump Then Fall, Today Was a Fairytale, Forever & Always, Haunted, Last Kiss and If This Was a Movie.

https://youtu.be/vP97PPdmxs4

Throughout their relationship, Taylor was often the special guest at Jonas Brothers’ shows across North America. In vlogs filmed for Taylor’s YouTube channel, Taylor was often spotted wearing Joe’s fedora - his signature style of 2008.

https://youtu.be/rJVYkPjQf9s

Taylor and Joe were media official as a couple by August, sitting together at MTV’s VMA Awards, and also hosting red carpet interviews together.

In September 2008, Joe was rumoured to be dating American actress, Camilla Belle, who he had met while filming a music video.

https://youtu.be/amh859mNeKI

In November 2008, when asked about her relationship Joe on The Ellen Show, Taylor responded with the news that they both had broken up - revealing that Joe has actually dumped her out of the blue in a 27 second phone call.

https://www.google.co.uk/amp/s/people.com/celebrity/joe-jonas-explains-split-from-taylor-swift/amp/

Joe immediately took to MySpace to deny the rumours that he had cheated on Taylor with Camilla Belle, explaining the split as a “change of heart”.

https://www.google.co.uk/amp/s/people.com/celebrity/its-official-joe-jonas-and-camilla-belle-have-split/amp/

Joe and Camilla publicly dated until July 2009.

https://youtu.be/euWniyJT5-g

In 2015, Joe began dating Taylor’s friend, American model Gigi Hadid. Taylor and Joe rekindled their friendship, and Taylor even went boating with the couple in June 2015 attended Joe’s birthday party in August 2015.

Gigi Hadid broke up with Joe in November 2015.

https://youtu.be/BuJA97QY5nI

In 2019, Joe married British actress, Sophie Turner, who Taylor is also friends with. Taylor congratulated Sophie Turner on The Graham Norton Show in May 2019.

[taylorswiftexlovers]

Sam Armstrong (2006-2007)

Sam Armstrong and Taylor met through friends in 2004 at Hendersonville High School, and dated between 2006-2007 before breaking up for a second and final time when Sam once again was caught cheating. Taylor has written numerous songs for Sam, including All Night Diner, Come In With The Rain, Should’ve Said No, Ten Dollars & a Six Pack, That’s When, Love To Lose, Matches, Stupid Boy, Tell Me, Look At You Like That, Rain Song, Tell Me Why, You’re Not Sorry, and White Horse.

Taylor incorporated Sam’s name as a hidden message in her song, Should’ve Said No (2006), by repeatedly capitalising every S-A-M in the lyrics.

Sam appeared on television game show in 2016 and admitted that after she’d caught him cheating on her in August 2006, he did and said everything he could in order for her to take him back, although he ultimately did it again.

https://twitter.com/sam23armstrong/status/966899701348950017?s=21

Sam has spoken of Taylor as recently as 2018, tweeting pictures of them together at prom in 2006 - although Taylor went as a partner to her friend, they took a couple shot together.

[taylorswiftexlovers]

James Dunlap (2005)

Known as Drew (an abbreviation of the middle name, Andrew) to friends and family, Drew and Taylor met through friends in 2004 at Hendersonville High School. Drew was in his senior year, whereas Taylor was still a freshman. Taylor and Drew dated for a year, before breaking up when Drew left Tennessee to attend college elsewhere. Taylor has written numerous songs for Drew, including Made Up You, Under My Head, You Do, Our Song, Fifteen, Perfect Have I Loved, Tim McGraw, By The Way, and Sweet Tea & God’s Graces.

https://youtu.be/VoAQv4kRwZQ

Taylor has spoken of Drew publicly as recent as 2019, bringing him up during a quick-fire round of questions on The Ellen Show when asked “Who’d you share your first kiss with?” replying “My high school boyfriend when I was fifteen. Drew.”

https://youtu.be/Pb-K2tXWK4w

Taylor references Drew in multiple lyrics from her song, Fifteen (2008), including “Hoping one of those senior boys will wink at you and say, “You know I haven’t seen you around before,””, “Then you’re on your very first date and he’s got a car and you’re feeling like flying, and your mama’s waiting up and you’re thinking he’s the one and you’re dancing round your room when the night ends.”, “When you’re fifteen and your first kiss makes your head spin round,”, “Back then I swore I was gonna marry him someday but I realised some bigger dreams of mine”.

https://youtu.be/T45WItzwHuE

In 2012 during whilst starring on VH1 Storytellers, Taylor also mentioned Drew ahead of performing Our Song (2006), explaining “This was a song that I wrote, actually to... sing at the high school talent show. I was a freshman. They had this talent show and I had just moved there, and I really wanted to play for my friends for the first time. I’d never told them really that I did this and that I love this and that I write songs. And I had been dating this guy who was so nice, and I wanted to write this song for us, and play it for him, and his friends, and for me, and for all my friends, and it was the high school talent show! And so I wrote this song and I included all these details about our relationship like how when we were on the phone really late at night my mom would patrol... she’d for real just be pacing outside my room in, like, figure eights, and I’d be under the covers like “I like you so much too! I know! I don’t want to get off the phone!” - Anyway, so my mom would be like “Taylor! Get off the phone! You have to sleep! It’s four in the morning! This is ridiculous! You will see Drew in the morning! This is ridiculous!” I wrote all these details about our relationship, like when we were riding in the car with me in shotgun, and like all those things.”

In Taylor’s freshman year of high school, Drew took her as his date to his senior prom in 2005.

http://tigerbeat.com/2008/09/taylor-swift-gets-personal-with-blog-girl/

In 2008, Taylor spoke with TigerBeat magazine about her first kiss with Drew, explaining “I was 15. I was one of the last of my friends to ever kiss a guy.” and that “I ended up dating him for a year.”

https://youtu.be/RkCNpFLbVVw

In 2006, Taylor spoke will Hill Country about the inspiration behind her song, Tim McGraw (2006), written towards the end of their relationship when Drew was close to finishing his senior year at their high school and would inevitably be moving away to attend college in another state. Taylor explained “After school I went in and wrote this song in fifteen minutes on the piano. You know, I think I applied it to the situation that I was in, in which I was dating a guy who was going off to college and I knew that we were going to break up and... just thinking of all the things that were going to remind him of me.”

After breaking up in August 2005 when Drew moved away from Tennessee for college, they remained good friends. Taylor kept the handmade necklace he’d given to her as a keepsake in her bedroom for several years, and both teens’ parents remained friendly with one another.