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.
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.
“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: