He dated Olivia de Havilland in the late 1930s and early 1940s and even proposed marriage to her, but she rejected the proposal as she believed he was not ready to settle down. She ended the relationship shortly before he began his military service, as she had fallen in love with director John Huston. In 1942, while serving in the military, Stewart met singer Dinah Shore at the Hollywood Canteen, a club mainly for servicemen. They began a romantic relationship and were nearly married in Las Vegas in 1943, but Stewart called off the marriage before they arrived, citing cold feet. After the war, Stewart began a relationship with co-star Myrna Dell during the filming of "The Stratton Story" (1949). Although gossip columnists made claims that they were planning to marry, Dell said this was not true.