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When Simon moved to England in 1964 he met Kathleen Mary "Kathy" Chitty (born 1947) on 12 April 1964 at the very first English folk club he played, the Railway Inn Folk Club in Brentwood, Essex, where Chitty was working part-time selling tickets. She was 17, he was 22 and they fell in love. Later that year they visited the US together, touring around mainly by bus. Kathy returned to England on her own with Simon returning to her some weeks later. When Simon returned to the US with the growing success of "The Sound of Silence" Kathy (who was quite shy) wanted no part of the success and fame that awaited Simon and they split up. She is mentioned by name in at least two of his songs: "Kathy's Song" and "America," and is referred to in "Homeward Bound" and "The Late Great Johnny Ace." There is a photo of Simon and Kathy on the cover of The Paul Simon Song Book.

Simon has been married three times, first to Peggy Harper in late autumn 1969. They had a son, Harper Simon, in 1972 and divorced in 1975. The song "Train in the Distance," from Simon's 1983 album, is about this relationship. Simon's 1972 song "Run That Body Down," from his debut solo album, casually mentions both himself and his then-wife ("Peg") by name.

His second marriage, from 1983 to 1984, was to actress and author Carrie Fisher to whom he proposed after a New York Yankees game.(The song "Hearts and Bones" was written about this relationship. The song "Graceland" is also thought to be about seeking solace from the end of this relationship by taking a road trip). A year after divorcing, Simon and Fisher resumed their relationship for several years.

He married folk singer Edie Brickell on May 30, 1992. They have three children together, Adrian, Lulu, and Gabriel.

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