In Superman’s Pal, Jimmy Olsen #36 (February 1959), the writers thought to introduce an occasional love interest for Jimmy in Lois Lane’s younger sister, Lucy Lane. Lucy is a blonde stewardess that Jimmy falls for immediately and does his geeky best to get a date with her. Finally succeeding, he amazingly decides to “pop the big question” on their first big date, but Lucy says that she promised she won’t get married until her sister Lois does, which means that Jimmy is stymied due to Superman’s feet-dragging. Oh well, We’re almost in the decade of “free love” and that should work just fine, right Jimmy?