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O'Connor and Rand met on a movie set, in the years of silent movies. They were appearing as extras. Rand was also writing scripts, and O'Connor building a movie and stage career. Rand admired O'Connor's looks, and tripped him on the set, to get him to notice her. They married in 1929.
To make sure they had enough income to succeed, O'Connor let his acting career go, becoming a rancher so Rand could succeed as an author, which was her ambition. He appeared in a presentation of her play Night of January 16th, after she became better known.
The couple had no children, but were friends with some college students and young professionals, including Nathaniel Branden (who later wrote psychology books, including important works on self-esteem), Alan Greenspan (economist, who served as Federal Reserve chairman for the United States government) and Leonard Peikoff (later author of philosophy works, and editor of Rand's works). O'Connor "played host" to many discussions and forums about human interaction, relationships and societies, while wife Rand led the conversations.
He found a new pursuit, as he developed a talent for painting. Some of Rand's books used his paintings as for their covers.