When: July 2012 — October 2012
Kennedy struck up an intense summer romance with Swift in 2012, which started that July when, as per E! News, they were first spotted together sharing lunch at a pizza place in Mount Kisco, New York. The rest of that summer was filled with plenty more supercute, supercouple-y activities between the two, like making out at his family's estate in Hyannis Port, MA, and splashing around in the ocean. It started to look like things between Swift and Kennedy weren't going so well when his family accused Swift of crashing the wedding of Kennedy's cousin Kyle in August, according to E! Her reps denied it, but it appeared the damage had been done. As the warmer months cooled off, so did Swift and Conor's relationship. They split by October.