Olive Cawley was one of Jack’s girlfriend during the spring of his last year at Choate. By the time he graduated from prep school she had become a regular date. He met her at the Choate spring dance and she was said to be very pretty.
Ever the non-romantic, however, JFK had warned her “Don’t fall in love with me!” In addition, Kennedy apparently regularly reported to Lem Billings on his ultimately unsuccessful attempts to have sexual intercourse with Olive.
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