Taylor Swift and Conor Kennedy’s Whirlwind Romance: A Look Back at Their Relationship Timeline

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Taylor Swift and Conor Kennedy’s Whirlwind Romance: A Look Back at Their Relationship Timeline

Young love! Taylor Swift and Conor Kennedy had a whirlwind romance worthy of a love song — which the musician seemingly documented in her hit “Begin Again.” The Grammy winner was first linked to Kennedy in the summer of 2012 after she was spotted spending time with the iconic family in Hyannis Port, Massachusetts over the 4th of July. Swift, who has been vocal about her love for the family over the years, was introduced to Conor after connecting with his aunt Rory Kennedy a year prior. The “Lover” singer was contacted by Rory for concert tickets in 2011, which is what started her friendship with the family. Swift later attended Sundance Film Festival’s January 2012 screening of Ethel, which is Rory’s HBO documentary about her mom and Conor’s grandmother, Ethel Kennedy. "She's a great friend of all of ours," Rory told reporters during the Television Critics Association panel in August 2012 after she invited Swift to visit the family’s compound one month prior. "She's awesome, and we love her." Ethel noted at the time that she wasn’t the Conor and the “Evermore” singer’s matchmaker, but she did comment on whether she could see Swift becoming a Kennedy down the line. “We should be so lucky,” the Kennedy matriarch told reporters at the TCA event. [jwplayer EbPir98l-zhNYySv2] After initially being linked to Conor’s cousin Patrick Schwarzenegger over the American holiday, the “Exile” songstress was spotted spending time with Conor on several occasions during the month of July, before Us Weekly confirmed their romance the following month. Following the death of his mother, Mary Kennedy, who died by suicide in May 2012, Swift has been a “real shoulder to cry on,” a source told Us in August 2012, noting that the country-turned-pop singer is “really smitten” with Conor. “She’s obsessed with the family,” a second source exclusively told Us of Swift in August 2012. The twosome’s romance, however, was short lived with them parting ways “quietly” in September of that year, according to an insider. "It was just a distance thing,” the source told Us in October 2012 of the “We Are Never Ever Getting Back Together” singer and the then-high school senior. “No hard feelings. They're fine." Scroll down to relive their whirlwind romance from beginning to end: [podcast_block]

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July 2012

The “Red” singer was seen spending time with Conor in Hyannis Port, Massachusetts, throughout the month, shortly after she sparked romance speculation with his cousin Schwarzenegger over the 4th of July.

Swift and Schwarzenegger were briefly linked when they were photographed along with some of his family members on the holiday.

Things between Swift and Conor heated up in late July as they were seen walking on the beach and playing on a trampoline, according to an eyewitness. "Conor put his arm around Taylor and they kissed behind the boat shed," the source told Us of the pair’s July 28 activities.

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August 2012

Us confirmed on August 1 that the duo were “officially dating” after Swift was spotted getting cozy with Conor the week prior in Massachusetts.

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August 2012

The Pennsylvania native purchased a home in Hyannis Port, Massachusetts, near the Kennedy compound for $4.8 million, according to Vanity Fair.

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August 2012

"She's head over heels," an insider told Us of Swift amid her whirlwind romance. "[She] is very smitten.”

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September 2012

Us confirmed in October 2012 that the duo parted ways the month prior after an intense couple of months together. "They quietly parted ways a while ago," a source exclusively said at the time.

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October 2012

Swift dropped her fourth studio album, Red, following her breakup from Conor. It is widely believed that the track “Begin Again” is about their split, with lyrics referring to a fresh start after heartbreak.

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October 2012

“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,” Swift told Katie Couric shortly after news broke that she and Conor had separated. “I don’t really know that much about love, it turns out.”

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March 2013

Swift sold her Hyannis Port mansion less one year after she first met Conor, E! News reported. The seven-bedroom home sold FOR $5,675,000 with the songstress making a nearly $1 million profit, according to Vanity Fair.

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November 2021

Swift released Red (Taylor’s Version) bringing attention back to her brief romance with Conor as well as Jake Gyllenhaal, who she dated in 2010. Both men were believed to be the subjects of her original Red album.