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In 1977 Edwin Schlossberg, an artist, designer and free-lance thinker, co-authored a book called The Philosopher's Game. It was an entertaining volume: On each page, Schlossberg and his partner, John Brockman, involved a famous thinker in a hypothetical debate (Machiavelli, for instance, trying diplomatically to advise the ruthless Cesare Borgia) and asked the reader to choose one of three philosophical quotes the sage would have used to illuminate the question at hand.

Today one has a sneaking desire to add a new example to the book. You are the 20th-century thinker Ed Schlossberg. You are attracted to a girl: a bright girl, a pretty girl, a girl whom her friend, George Plimpton, calls "a marvelous creature." But there are problems. You are 41 and she is only 28. You are Jewish and she is Irish Catholic. What's more, she is the only daughter of an immensely charismatic, assassinated President and his gorgeous wife, and her days, despite her wishes, are lived in the fishbowl of public life.

If you're Ed Schlossberg, what do you do?

The answer appeared in a 41-line announcement on the society page of the March 2 New York Times. Jacqueline Kennedy Onassis of New York was pleased to announce that her daughter, Caroline Bouvier Kennedy, "the daughter also of the late President John Fitzgerald Kennedy," was engaged to author and executive Edwin Arthur Schlossberg, and a summer wedding was planned.

The announcement itself was not a surprise. After all, Caroline, now a first-year law student at Columbia University, and Schlossberg, an intellectual jack-of-all-trades and friend to New York's cultural nobility, had been seeing each other for five years. But the timing threw social savants for a loop. A New York gossip columnist had suggested just days before that the two might be holding off indefinitely for fear a marriage outside her faith might upset the bride-to-be's grandmother, family matriarch Rose Kennedy, 95. Schlossberg's father, Alfred, has never met Jackie. And unlike the other planned Kennedy clan wedding—of Maria Shriver and Arnold Schwarzenegger, scheduled for April—there had been few pre-engagement hints.

But if any arguments did stand in the way of the union, they have obviously been overcome. Caroline and Ed spent the weekend of their announcement at Hyannis Port where they accompanied Rose, who was in a wheelchair, on a brief outing near the family compound. Alfred Schlossberg has stated that his future daughter-in-law is a "lovely girl." And as for the lack of preannouncement publicity, that may say as much about the character of the couple as any article or gossip item. Caroline has long been the "private Kennedy," nurtured in that role by her mother. In the six-foot, graying Schlossberg, she may have found the perfect combination of what she likes about her family—intelligence and humanism—coupled with her own distinguishing trait, a desire to lead a life away from the public eye.

Caroline was never an archetypal Kennedy kid, as defined by the high-powered, hyperactive children of Bobby, "that garrulous social clan...with energy that's like 88 locomotives," in Plimpton's words. Instead, in the years after she had begun to recover from the immediate shock of her father's death, she was a curious child and whimsical. "When she was 7 or 8," Plimpton remembers, "we'd lie on the floor and have the most amazing adult conversations. It was enchanting to talk to someone that young with that sort of fancy." Jackie Kennedy reportedly made a point of not exposing her children to too many celebrities. "She didn't spoil them," says a friend. "She invited their father's old friends to dinner, not Nureyev."

Barbara Gibson, former secretary to Caroline's grandmother and author of the just published Life With Rose Kennedy, remembers that "If there was a group of cousins, she'd be in the back. She was very well-mannered, very quiet, cooperative, poised and calm, unlike many of the other children. Caroline was the most trustworthy—I would lend her my car."

If you are a Kennedy, however, sometimes it is impossible to evade the limelight. Although Jackie, especially after her much-publicized wedding to Aristotle Onassis, jealously guarded her children's privacy in the family's 15-room Fifth Avenue apartment, there was no stopping the paparazzi outside the front door. Caroline was not rude to photographers (her grandmother once admonished her to be nice to them because they might get in trouble at work if they didn't get a picture of her), but she never pretended that they made life easier. Attending Concord Academy and graduating from Radcliffe with a fine arts degree, she hoped for a while to go into photojournalism, but found her name a mixed blessing. In 1977, working as copy girl for the New York Daily News, she stopped at a nearby deli for lunch and was chagrined when pictures of her, taken by lurking photographers and released via UPI, made their way back to the newsroom moments before she did. A co-worker from that time, Richard Licata, remembers her as "very bright, amiable and friendly," but frustrated. Talking about a reporting assignment she had gotten from Rolling Stone, she told him, "They want me to write it just because my name is Kennedy. I really haven't done anything with my life yet."

After finishing college she shared an apartment on Manhattan's West Side with three roommates (two male, one female). She got a job as a researcher in the office of film and television at the Metropolitan Museum of Art, and later became a manager and coordinating producer. She partied, but not quite as heartily as her cousins (although one date remembers Jackie getting on the line during his phone call with Caroline and saying, "I hear you went to a crazy party last night—you should have told me about it"). And for 2½ years she had a steady boyfriend, writer Tom Carney. They split in 1980, and Caroline was an unattached woman when she met a slightly older young man, Ed Schlossberg, at a dinner party.

Friends routinely append the word "brilliant" to Schlossberg, as though it were part of his name. He grew up on Park Avenue and attended the exclusive Birch Wathen School, where he was head of the social committee and captain of the soccer team. It was during his years at Columbia that two enduring traits exhibited themselves: his intelligence and his unwillingness to limit its use to just one discipline. In 1971 he graduated with two Ph.D.s, one in literature and one in science. His thesis posed an imaginary dialogue between Albert Einstein and playwright Samuel Beckett.

Starting in his graduate student years Schlossberg became friends with such eclectic old lions of the cultural-intellectual kingdom as Buckminster Fuller, Norman O. Brown and John Cage. ("He was," says an acquaintance, "a great charmer of old men and young women.") Like many intellectuals, he immersed himself in a jumble of seemingly unrelated fields. As an author he has written or co-written nine books, including volumes on home computers and games to play with pocket calculators. As an artist he has painted simple poetic phrases on various surfaces, including, for designer Willi (Willi Wear) Smith, specially treated T-shirts whose slogans turned different colors depending on the wearer's body temperature. In his most bourgeois incarnation, he runs a company that designs museums and exhibits: For a children's museum in Brooklyn, he built models of molecules big enough to walk through; for the Massachusetts SPCA, he created exhibits that, among other things, enabled visitors to view the world through a pig's eyes. Says his agent, John Brockman, who met him about 20 years ago at a seminar run by avant-garde composer John Cage: "You can't get a fix on him, because as soon as you do, he moves on to something else. He's incredibly imaginative." Occasionally, Schlossberg, whom Plimpton characterizes as "terribly bright—a looming figure, very high intensity," would simply sell himself as a free-lance intellect, charging consulting fees of $500 a day. This no doubt helped him maintain his two domiciles: a loft in lower Manhattan and a converted barn in the Berkshires that one guest describes as "extremely comfortable—more like Country Living than House & Garden."

Schlossberg and Kennedy were an item almost from the moment they met. After three months he reportedly gave her a VCR as a house warming gift for her new one-person apartment. "They seemed very lovey-dovey," says one observer, who adds that Schlossberg can be extremely protective of Caroline. "He had his arm around her for two hours—at a meeting she was supposed to be in charge of." On the other hand, a little over protectiveness is perhaps justified. A few months into their relationship, Caroline received a series of threatening John Hinckley-like letters from a California law school graduate who wanted to marry her. The man was later arrested. Three years later a 32-year-old drifter tried to break into her office at the Met, intent, he said, on proposing marriage. Schlossberg also helped console Caroline after the death of her cousin David from a drug overdose in 1984.

Schlossberg seems to have been accepted by the Kennedys. "Everyone thinks he's great," Douglas Kennedy, Bobby's son, told reporters at Hyannis. "We see them a lot." Schlossberg has attended Mass with Caroline "many times," according to another relative, and the ceremony this summer is expected to be a church wedding. Family and friends agree that the age difference is a nonissue: John Kennedy was, after all, 36 when he married 24-year-old Jacqueline Bouvier. One by one, any objections and obstacles seem to have melted away. Aware that Schlossberg has shown little inclination toward rough-and-tumble exercise, Barbara Gibson observes that "they probably won't ask him to play touch football on Thanksgiving afternoon, but the family likes him."

If the proposed marriage were a chapter in Schlossberg's book The Philosopher's Game, which of the following philosophical axioms would it suggest?

A. All mankind love a lover.
—Ralph Waldo Emerson

B. Love begets love.
—Robert Herrick

C. Love conquers all things.
—Virgil

The correct answer is probably all of the above.