This caused some friction with his best friend Don Kaye, who had also been wooing Mary Jo, to the point where Kaye refused to attend Gygax's wedding.: 47 (Kaye and Gygax reconciled after the wedding.) The young couple moved to Chicago where Gygax continued as a shipping clerk at Kemper Insurance, and also found Mary Jo a job there too. Gygax was smitten with the beautiful young woman, and after a short courtship, persuaded her to marry him, despite the fact that he was only 19.

At about the same time that he discovered Gettysburg, his mother re-introduced him to Mary Jo Powell, who had left Lake Geneva as a child and had just returned. It was also from Avalon Hill that he ordered the first blank hexagon mapping sheets that were available, which he then employed to design his own games. Shortly after his return, a friend introduced him to 's new wargame, and Gygax was soon obsessed with the game, often playing marathon sessions once a week or more. By the time he reached his teens, Gygax had a voracious appetite for authors such as, and.: 40 Gygax was a mediocre student, and in 1956, a few months after his father died, he dropped out of high school in his junior year.: 43 He briefly joined the Marines, but after being diagnosed with, he was given a medical discharge and moved back home with his mother.: 49 From there, he commuted to a job as shipping clerk with in Chicago. As teenagers Gygax and Kaye designed their own miniatures rules for toy soldiers with a large collection of 54 mm and 70 mm figures, where they used 'ladyfingers' (small firecrackers) to simulate explosions. His interest in games, combined with an appreciation of history, eventually led Gygax to begin playing in 1953 with his best friend. His father introduced him to science fiction and fantasy through.

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