A perfectly well-intentioned person she has never met approaches her to say that a relative is entering politics because of her father, John F. Kennedy. Or expresses sympathy for the loss of her brother, John F. Kennedy Jr., who died in a plane crash in 1999, or her mother, Jacqueline Kennedy Onassis, who succumbed to lymphoma in 1994.
These interactions happen on the subway (the main way she gets around New York). They happen on Martha's Vineyard (where she spends her summers). They happen at the ballet, at the movies, when she is on a book tour and when she's visiting one of New York's public schools, a cause she has been involved in for years.
Kennedy is said to be patient and gracious during these encounters, as she deflects and gently parries, leaving the other person feeling as if he or she has had a significant conversation, even if almost nothing at all was really said.
Sounds like perfect training for an ambassador.
On Wednesday, the Obama administration nominated Kennedy, 55, as the next U.S. ambassador to Japan, which would give her the kind of formal public role many have long predicted for her (but that had seemed permanently derailed by the off-and-on-and-then-finally-off flirtation with Hillary Rodham Clinton's vacated Senate seat in 2009).
As a longtime family friend, director Mike Nichols, said, it's a job for which Kennedy is ideally suited. After all, he said, "In the course of her life, what has she learned if not diplomacy?"
The position is a particularly interesting one for Kennedy, a crucial supporter of President Barack Obama during the 2008 campaign. Unlike other high-profile postings like those in London and Paris, which have often been filled with prominent social figures (Kingman Brewster Jr., Pamela Harriman) or prodigious fundraisers (Arthur Watson, Charles H. Rivkin) or both (Walter H. Annenberg), the one in Tokyo has often been for notable politicians nearing the end of their careers (Mike Mansfield, Thomas S. Foley, Walter F. Mondale and Howard Baker, to name a few), a testament to the importance of Japan as an ally and the premium that society places on status. (The current ambassador is John V. Roos, a lawyer and major fundraiser for Obama.)
In addition to describing her as a person who has dedicated herself to public service, Mondale, the vice president under Jimmy Carter and the ambassador to Japan from 1993 to 1996, said that Kennedy's famous last name should serve her well.
"The Japanese will be thrilled with this news," he said in a phone interview. "She will be very popular. They love the Kennedys over there. They've worked with several of them, and they appreciate their position in public life. They know she's an American star, and they know she's a serious person and that she'll be well-prepared. It will be a strong embassy under her leadership. I think they're honored."
Kennedy would not comment for this article, pointing out through a spokeswoman that she has not yet been confirmed. But friends said that the appointment would reflect a lifelong desire to serve, noting that she has written several well-regarded books on public policy and leadership. Some also suggested that Japan's somewhat more formal culture might inoculate Kennedy from a certain amount of what she endures in this country when she is in public.
Or, at least, this is what her longtime book agent, Esther Newberg, thinks.
"It's brand new, and it's different," Newberg said, adding that she was excited that her friend might not have to "go through the same process she goes through every time a book comes out and there's a new group of people saying the same things to her they think are fresh and new and that she's never heard before."
Over the years, Kennedy has done all sorts of things on behalf of her family's legacy. She took on a crucial role at the John F. Kennedy Library that only increased when her uncle Edward M. Kennedy died in 2009. She has served on the boards of organizations like the Commission on Presidential Debates and the NAACP Legal Defense and Educational Fund, both of which were causes dear to her family's political philosophy.
Said Kenneth R. Feinberg, the head of the John F. Kennedy Library: "As the sole surviving member of President Kennedy's family, she is the guardian of the flame. It is an awesome responsibility, and she does it extremely well."
Still, in recent years, some friends say that Kennedy has begun to think of how she might carry on that legacy in a less direct way.
Although few of her friends wanted to discuss it (Kennedy, they say, would be loath to admit how taxing some of the public condolences can be, viewing such complaints as spoiled or victim-like), more than a few expressed relief that the ambassadorship is coming just months before the 50th anniversary of her father's death and that the posting might give her the convenient opportunity to be out of the country when it occurs.
The fact that her children - with her husband, Edwin Schlossberg, whom she married in 1986 - have grown up and embarked on their own careers has made it possible for her to think about making a move, or to "pivot," as her cousin Tim Shriver put it in a phone interview.
Her daughter Rose, 25, is working for television writer and producer David Milch. Tatiana, 23, worked as a reporter at The Record in New Jersey and is pursuing graduate studies at Oxford. Jack, 20, a student
at Yale, is a certified EMT and was the roommate of Eli Rivkin, whose father, Charles, is finishing his stint as the ambassador to France.
"The great privilege of her life is growing up with so much to be proud of, and so many opportunities open to her," Shriver said. "The great challenge is to become her own person within all that. That's pop-psych 101. It's no big insight, but it's true. And I think this is a moment in which she can peel back the layer of the Kennedy and open up the layer of the Caroline."
The job would also give her the opportunity to serve Obama, whom Kennedy endorsed in January 2008.
At the time, Obama was in a nail-biter of a primary with Clinton, whose husband, the former president, had enjoyed a warm and long-standing relationship with Kennedy and her uncle Teddy. But Kennedy's children were all more enthusiastic about Obama than they were about Clinton. And to Kennedy, this counted for a lot.
In a January 2008 Op-Ed column in The New York Times, "A President Like My Father," she wrote that Obama "has built a movement that is changing the face of politics in this country."
In part because Kennedy made her endorsement early on, she earned a lot of good will from Obama and members of his team. She became close to David Axelrod, who ran the 2008 campaign. He recalled that, in an early meeting, she saw Obama's communications director Robert Gibbs wearing an Obama fleece that she liked.
"She said, 'That's really cool, where can I order one?'" Axelrod said. "And he said, 'We'll order one.' She said: 'No, no, that's fine. I'll order one.' So we became friends."
When Obama won the nomination, Kennedy was given a leadership role, working with Axelrod on the search committee for the vice presidency. Later, Kennedy persuaded Axelrod to join the board of the Institute of Politics at Harvard, her alma mater.
Throughout their time together, Axelrod said, Kennedy was diligent and focused and came to the table without any sense of entitlement.
That's how Bob Hughes, the head of New Visions for Public Schools, described her as well. Hughes got to know her when she went to work for the Department of Education in 2002 as a fundraiser. He said that the first time he met her, "we were chitchatting in the hall."
"She's iconic," he said. "We were a little intimidated. But she immediately puts people at ease."
In short order, he was exchanging emails with her about matters ranging from W.H. Auden to the Catholic Church.
Eventually, Kennedy came aboard his organization as a board member, strategizing on ways to improve academic performance and becoming involved in labor negotiations with teachers in the public school system.
"Anybody who knows about labor negotiations knows it's as fun as going to the dentist with no Novocain," Hughes said.
But she had made it clear that she wasn't interested in a typical role as a celebrity spokeswoman for the organization. And over time, he and Kennedy became involved in other endeavors together.
A few years ago, Hughes made an offhand comment that he and his partner, Dr. Richard Friedman, a psychiatrist who directs the psychopharmacology clinic at NewYork-Presbyterian/Weill Cornell hospital, made a ritual of competing in Swim for Life, a 1.25-mile event in Provincetown, Mass, that raises money for AIDS and women's health charities.
"She said, 'Oh, I'd really like to do that,'" Hughes said.
And so, Kennedy did. "She just showed up and changed in a gas station and came out and did the race," Hughes said. "It was pretty choppy, and she did a terrific job. I'm happy to say I beat her. But just barely."
Back at home, Kennedy leads what is by all accounts a fairly quiet existence. Although she sits on several boards and has a wide group of friends, she is hardly a fixture on the social circuit. Most nights, she is at home with Schlossberg, who is said to be quieter and more indoorsy than his wife. (An architect with an interest in progressive design culture, Schlossberg is said to be game for the adventure of going abroad.)
When the couple does entertain at their Upper East Side apartment, guests come from a variety of fields. Joel I. Klein, the former New York City schools chancellor, and his wife, Nicole K. Seligman, the president of the Sony Corp. of America, are frequent guests. So is Richard Plepler, the head of HBO.
Plepler, a friend of hers for many years, recalled holding a dinner party in 2003 at which almost all of the guests were in favor of invading Iraq.
"The only person at this table who eloquently dissented was Caroline," Plepler said. "I remember it very vividly, in part because she likes to remind me that she was right and I was wrong. But I think that's reflective of her judgment and how well read and how well informed she was. It was a formidable table, and she was not bashful about saying, 'You're all mistaken.'"
Nichols described going over to Kennedy's apartment last November to watch the election returns come in.
"I walked in, and she said, 'Oh, go find Rupert, he's in the library. It's quiet in there.'"
She was referring, of course, to Rupert Murdoch, head of the News Corp.
"It's the Washington thing: who you work for, what your beliefs are entirely beside the point," he said of Kennedy's attitude. "Everybody is with everybody."
And that's part of what he thinks will serve Kennedy well in her position in Japan, where she would likely do everything from entertaining at the embassy to meeting with foreign dignitaries and politicians with a variety of ideological persuasions.
"If anybody knows those rules," Nichols said, "it's her."