America’s Sweethearts

Advice for Taylor Swift on Her Romance With Conor Kennedy

Dating a Kennedy, never mind marrying one, is fraught with peril. Rebecca Dana compiles history’s lessons on the subject.

Taylor Swift has recently embarked on one of the most dangerous adventures a pretty young button-nosed Caucasian woman can take. She is dating a Kennedy. After a few weeks in Hyannis Port on the arm of 18-year-old Conor, son of Robert Kennedy Jr. and the late Mary Kennedy, Swift, 22, has been “swept off her feet.” They are taking long walks arm in arm in front of the paparazzi. They are sharing pizza in Mt. Kisco, N.Y. They are bouncing on trampolines together and petting Labradors.

Things have gotten so hot and heavy that, as happens in any youthful romance, Swift reportedly sent a home inspector to investigate the $4.9 million estate next door to the Kennedy compound, with thoughts of buying it.

With this, the chipmunk-cheeked actress and pop-music sensation joins the very deep ranks of women who’ve flirted with America’s royal family. Before she takes a leap off her own private dock, Swift would do well to learn from the experiences of these many exes and the few who ended up as Mrs. Kennedy. Conor is by all accounts a caring and sophisticated soul, but no man can completely outrun his DNA. The fact remains: Kennedys do not have the world’s best track record when it comes to women. Herewith, a few of history’s lessons for the girl who catches a Kennedy’s eye:

Do: Have your own money. The most successful Kennedy paramours (and alleged paramours) came in with their own identities and their own bank accounts. Better to be Gloria Swanson, whose fame and success managed to survive an ultimately damaging affair with patriarch Joe Kennedy, than to be written into history books as “Faddle.” One model for this is Suzy “Chapstick” Chaffee, the actress and alpine skier, who credited the rumors of her affair with Ted Kennedy for the passage of the Amateur Sports Act of 1978. Chaffee emerged intact from her association with the Kennedy clan and went on to be the first woman to serve on the board of the U.S. Olympic Committee. There is also the issue of Kennedys not always being the most financially savvy men. “It was famous among Jack’s group of friends that he never carried any money. He just didn’t seem to think about details like that, but somehow the bill always got paid,” wrote JFK girlfriend Jayne Blodgett Murray in her autobiography, The River’s Bend. Swift, who has sold 22 million albums and 50 million singles and has earned more than $57 million in her short lifetime, is already well ahead of Conor, best known previously for his severe food allergies.

Don’t: Get involved with more than one Kennedy. It may already be too late for Swift to keep her Kennedy affections to one. She began the summer amid rumors of a relationship with Patrick Schwarzenegger, son of Arnold and Maria, and is ending it with Conor, though Swift swears she and Patrick were never more than close friends. An earlier generation of Kennedy men were notorious for sharing women. JFK and RFK both allegedly dallied with Marilyn Monroe. Mimi Alford, the former White House intern who wrote of losing her virginity to JFK in Mrs. Kennedy’s bedroom, tells a particularly gruesome story in her book Once Upon a Secret of a time the president tried to persuade her to sleep with his brother Ted, claiming he looked a little “tense.” There is no reason to imagine Conor has the same transparent disdain for the women in his life, but as a general principle, the “one per family” policy is sound.

Do: All the driving. Leave aside whether you believe in the mythical Kennedy Curse, thought to have plagued the family for generations. Think not of Mary Jo Kopechne, the would-be lady friend to Ted Kennedy who died at the bottom of a tidal channel in Chappaquiddick in 1969 after he took a wrong turn and drove them off a bridge. Think not of JFK Jr., who died in 1999 while piloting his own plane, taking his wife and sister-in-law with him. Think not even of Kerry Kennedy, who blamed a recent car wreck on a seizure. Teen boys are the most dangerous drivers in America, accounting for 30 percent of the total cost of motor vehicle injuries in the country. Why tempt fate? Better yet: Hire a chauffeur.

Do: Respect the matriarchy. A Kennedy man loves his mother. A Kennedy man is terrified of his mother. And probably with good reason. Early JFK Jr. girlfriend Christina Haag tells a story in her memoir about a Caribbean vacation when he steered their kayak into a boulder. “I saw John, my captain: John, who was never afraid. Unable to be still, he paced around the beach muttering something, his eyes wide and to the ground. ‘Don’t tell Mummy, don’t tell Mummy,’ he repeated like a mantra to no one.) Swift is in good shape on this front: Ethel Kennedy, Conor’s grandmother, said she’d be thrilled to have Swift in the family: “We should be so lucky.”

Don’t: Marry a Kennedy. They can be great to date, but a sensible woman is advised against marrying a Kennedy man. During their affair, Joe Kennedy brought Gloria Swanson home to dinner with his wife, Rose. Ted Kennedy allegedly slept with more than 1,000 women throughout his married life and paid $10 million in hush money to cover up the affairs. Neither JFK nor RFK—nor their junior versions—was ever winning Husband of the Year. That said, both Conor and Patrick have had to endure the public airing of their parents’ extreme marital woes. Perhaps the next generation of Kennedys will turn out to be model spouses.

And when all else fails, do: Have a way with words. Many a successful former Kennedy girlfriend has survived the demise of her relationship and managed to channel the experience into literature. Swift has a jump on this as well. Rory Kennedy, Conor’s aunt, told ABC News that the singer, who has “read a ton of books about our family,” has already begun to commit her feelings to paper: “She was inspired and wrote a song.” This should be enough to scare the Kennedy family straight. Just ask Taylor Lautner, Joe Jonas, John Mayer, Jake Gyllenhal, and all the other boys who’ve been the subject of multi-platinum pop ballads. The only thing more dangerous than a young woman dating a Kennedy is a young man dating Taylor Swift.