In December 1939, both Olivia de Havilland and Jimmy Stewart were traveling to New York City. Olivia was going to attend the city premiere of 'Gone With The Wind' at the Astor Theatre, while Jimmy was planning a Christmas visit to his sister. Coincidentally, Irene Mayer Selznick, who was a significant figure in the entertainment industry, proposed to Jimmy's agent, Leland Hayward, that Jimmy accompany Olivia to her high-profile event. This suggestion piqued Jimmy's interest, as he had met Olivia briefly in Hollywood and jumped at the opportunity to further acquaint himself with her.
“Jimmy met me at LaGuardia airport,” Olivia recalled to James Fishgall, author of Pieces of Time: The Life of James Stewart. “He even had the limousine drive out to the airfield. We were both quite shy and ventured one word at a time in our conversation.”
The kind of conversation they had must have been rather compelling. In no time, they became extremely close, spending almost every evening dining together, and frequently attending the most recent Broadway plays. Being a certified pilot, Jimmy used to enjoy taking Olivia for fly-overs across the Pacific, he even taught her a few flying lessons. Alongside this, they enjoyed engaging with his model aircraft, having picnics in the forest (bringing along a portable record player), and occasionally, they would settle by the lounge, engross with a book each, falling into relaxation in the end. The closeness between them was so palpable that as of spring 1940, fan magazines were hinting about a possible elopement.
Despite the Hollywood glamour encompassing their lives, Jimmy and Olivia were more invested in world affairs, their perspective stretching far beyond the trivial contrivances of the showbiz industry. With the looming Nazi menace burgeoning atrociously, England, the birthplace of Olivia's parents and where her father still resided, was somewhat isolated in its resistance against the Third Reich. This was a time when other countries across Europe started to crumble.
In August 1940, as the production of The Philadelphia Story concluded, Stewart took the initiative to organize a fundraiser to aid Britain's strained forces. This event took place at the Sam Houston Coliseum in Texas, where Olivia, Tyrone Power, Mischa Auer, and Jimmy's former roommate and close associate Henry Fonda took center stage. Fonda partnered with Jimmy for a magic stint, complementing Jimmy's accordion tunes with his cornet.
March 1941 saw Jimmy join the army, nine months before Pearl Harbor was bombed. Despite efforts to maintain their relationship, distance took its toll, leading to their eventual parting. Olivia, in the subsequent year, initiated a relationship with John Huston, who directed her in 'In This Our Life.' Huston and Errol Flynn, according to reports, had a conflict over Olivia, marking the official end of their romance.
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Throughout their one and a half year relationship, Jimmy, known for dating numerous Hollywood celebrities, did propose. However, Olivia, despite being eight years his junior, questioned his maturity level.
“I think his offer of marriage was just a frivolous thing on his part,” she said years later. “Jimmy wasn’t ready for a wife—I guess he still had a few more wild oats to sow.”
“I think they got closer to the altar than was known at the time,” Jimmy’s friend, former MGM publicist Jerry Asher, recalled in Lawrence Quirk’s James Stewart: Behind the Scenes of a Wonderful Life. “But they ‘scaredy-catted’ out of it. They were a lot alike, Livvy and Jim. Prim, well brought up, decent, considerate, but as romantic and sexy as any guy or gal around.”
But both later said they wished they’d made a film together. In 1950, Jimmy was the one who handed over the Best Actress Oscar to Olivia for her stellar performance in "The Heiress".
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