“Jack’s greatest success in his first two years at Harvard was in winning friends and proving to be ‘a lady’s man’…

Jack’s discovery that girls liked him or that he had a talent for charming them gave him special satisfaction… ‘I can’t help it,’ he declared with evident self-pleasure [in a letter to an adolescent friend] . ‘It can’t be my good looks because I’m not much handsomer than anybody else. It must be my personality.’…

Jack’s easy conquests compounded the feeling that, like the member of a privileged aristocracy, of a libertine class, he was entitled to seek out and obtain what he craved, instantly, even gratefully, from the object of his immediate affection. Furthermore, there did not have to be a conflict between private fun and public good. David Cecil’s The Young Melbourne, a 1939 biography of Queen Victoria’s prime minister, depicted young British aristocrats performing heroic feats in the service of queen and country while privately practicing unrestrained sexual indulgence with no regard for the conventional standards of monogamous marriages or premarital courting. Jack would later say that it was one of his two favorite books.

One woman reporter remembered that Jack ‘didn’t have to lift a finger to attract women; they were drawn to him in battalions.’ After Harvard, when he spent a term in the fall of 1940 at Stanford (where, unlike at Harvard, men and women attended classes together), he wrote Lem Billings: ‘Still can’t get use to the co-eds but am taking them in my stride. Expect to cut one out of the herd and brand her shortly, but am taking it very slow as do not want to be known as the beast of the East.’

But restraint was usually not the order of the day. He had so many women, he could not remember their names; ‘Hello, kid,’ was his absentminded way of greeting a current amour. Stories are legion — no doubt, some the invention of imagination, but others most probably true — of his self-indulgent sexual escapades. ‘We have only fifteen minutes,’ he told a beautiful co-ed invited to his hotel room during a campaign stop in 1960. ‘I wish we had time for some foreplay,’ he told another beauty he dated in the 1950s… At a society party in New York he asked the artist William Walton how many women in the gathering of socialites he had slept with. When Walton gave him ‘a true count,’ Jack said, ‘Wow, I envy you.’ Walton replied: ‘Look, I was here earlier than you were.’ And Jack responded, ‘I’m going to catch up.'”

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Again from Dallek’s great biography, An Unfinished Life: John F. Kennedy, 1917-1963, this excerpt pulled from chapter 2 (“Privileged Youth”).