Taylor dated Robert F. Kennedy's grandson Conor Kennedy during the summer of 2012. She did receive some criticism for the age difference in this relationship, being that she was 22 and Conor was an 18-year-old high school senior. However, Taylor purchased a house near the Kennedy compound in Hyannis Port, Massachusetts, during this relationship.

"Begin Again" has been linked to Conor, especially the line " I think it's strange that you think I'm funny 'cause he never did."