What an Unnamed Friend Revealed About Taylor Swift Dating 'Younger Men': 'Technically Jailbait'

Is Taylor Swift 'boy crazy?' The Shake It Off singer was once interviewed by Vanity Fair about music, revenge diss tracks about her exes, her relationship with the tabloids, and dating younger men. The now-34-year-old pop star went out with many young men, including teenagers like guys who were barely 17 years old. However, Swift's friend seemingly defended this notion against her. 

Apparently, she dated two such young guys, Conor Kennedy, the son of Robert F. Kennedy Jr., was just 17 years old and a senior at Deerfield Academy. However, her unnamed friend said it was nothing but a mere coincidence and defended the Lover singer. The friend explained, "[Conor was] just like a two-month thing," and said that Swift told her "he was awesome." But she also insisted this youthfulness was more of an issue instead of a benefit. 

The friend further argued that Swift also dated older men, "It was like a pendulum for her, swinging back and forth. She dated Jake [Gyllenhaal] and John [Mayer] when she was really young and they were in their 30s, and she got really hurt. So it was like 'That hurt—this won't hurt.' But then it did." 

Meanwhile, Swift admitted her fascination with the Kennedy clan dates far back, even before she began dating Connor. In 2011, the singer/songwriter told The New Yorker, "I'm just so obsessed with the whole history of J.F.K. and R.F.K," adding that she recently finished reading the 900-page book called The Kennedy Woman. 

Moreover, the Love Story singer's dating history has faced media scrutiny. Although she's been with men of fame, her romance with Connor gained much traction due to their social statuses. On the surface, the two appeared to be a power couple that, at one point, had a seal of approval from their families, including the Kennedys. 

Swift and Connor had been photographed kissing, and then they were also spotted holding hands at the gravesite of his deceased mother, Mary Kennedy, who committed suicide in May 2012. When grandmother Ethel Kennedy was asked how would she feel having Swift as her 'granddaughter-in-law,' she gushed, "We should be so lucky." Rory, Ethel's daughter added, "There is a mutual admiration society between my mother and Taylor Swift and I just love it." 

However, unfortunately, despite the couple's efforts to keep their relationship afloat, it ended within two months by October 2012. A source close to the couple told US Weekly that they called it quits because of distance and scheduling conflicts and left each other on good terms. And like she always does, Swift immortalized her romance with Connor by adding a few nods in her album Red in the song Everything Has Changed. 

Though Swift has often been labeled 'America's sweetheart,' her dating life has always been a point of contention for many of her critics. She even acknowledged the same in the interview: "What it ended up adding to was this whole kind of everyone jumping on the bandwagon of 'Taylor dates too much,' which, you know, since 2010 I have dated exactly two people." From Joe Jonas to John Mayer to Harry Styles to Tom Hiddleston to Joe Alwyn, Swift has 12 publicly known exes. Currently, she's head over heels in love with NFL star Travis Kelce.