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(31 August 1918 - 30 December 1922) (divorced)
Jack met Olivia when he had just started out in films. He almost married her immediately on sheer impulse being so alone, and she seemed to understand him. However, very soon after they did decide to marry, it became apparent that they were not well suited. Times were hard in the film industry at the time and because it was hard to support two, Olivia went back home. The plan was for Jack to send for her when times were better, but when things got better Jack found that he was happier without her. By that time, he had met his second wife, Leatrice and he therefore, asked for a divorce. It was a long time coming and his second marriage might have had a better chance for success if Olivia hadn`t held out so long to agree to the divorce.
His first marriage was to Olivia Burwell, a native of Mississippi whom Gilbert had met after her family moved to California, on August 26, 1918. They separated the following year and Burwell returned to Mississippi. Burwell filed for divorce in 1921.