My notes are in blue.
The setting: New York, December 19, 1939. The NY premiere of Gone With The Wind at the Astor Theater. Olivia was scheduled to attend.
Jimmy, eight years older than Olivia, was on the east coast for the holidays; his hometown was the small town of Indiana, Pennsylvania (his father owned a hardware store in town). Jimmy was visiting his sisters in New York around the time of the GWTW premiere.
While Stewart was in Manhattan, Lelan Hayward (Stewart's agent) asked if he would escort Olivia de Havilland to the New York premiere of her latest film, Gone With the Wind. The fix-up had been the brainstorm of Irene Mayer Selznick, wife of the film's producer, David O. Selznick. Stewart didn't know the actress, but he had read in a gossip column that she wanted to meet him, so he eagerly complied with his agent's request.
"Jimmy met me at La Guardia airport," de Havilland recalled, "even had the limousine drive out to the airfield - we were both quite shy and ventured one word at a time in our conversation." Still, a definite spark passed between them. Over the next few days, Stewart took her to the theater several times and to the "21" Club. She recalled that one of the plays they saw as Mornings at Seven, directed by Jim's old friend Josh Logan, whom she met for the first time backstage.
Jim and Olivia continued to see each other after they returned to Los Angeles. On one occasion, Stewart arrived at her Spanish-colonial house in the Hollywood hills driving his brand-new La Salle convertible. She was impressed until the automobile began making a weird groaning sound and they started rolling down the hill. The brakes had failed! Jim took off in pursuit, but the La Salle picked up speed down the incline, denting other cars and ruining curbside shrubbery along the way. Finally, it crashed into a telephone pole. Naturally, Stewart, who had been trying to impress his date, was terribly embarrassed, but she laughed and thanked him for the entertainment. They then continued their evening as planned - in her car.
Around the same time, actress Maureen O'Hara remembered having dinner one night at de Havilland's house. A fish that Stewart had caught was the main course. It was fine, but they decided to play a prank on him by telling him it had made them sick. "But he didn't pay the slightest bit of attention," O'Hara recalled, laughing. "He knew."
The 12th Academy Awards, honoring films in 1939, was held on February 29, 1940 at a banquet in the Coconut Grove at The Ambassador Hotel in Los Angeles. Olivia and Jimmy were both nominated for Oscars. Jimmy was up for Best Actor for Mr. Smith Goes to Washington (He lost to Robert Donat in Goodbye Mr. Chips) and Olivia was up for GWTW.
Below: footage from the Oscar ceremony that night. As you can see, they arrived separately that night at the dinner (I can't tell who their dates are).
Update (August 2015): A big thanks to some readers of the blog who believe Olivia's date is Jock Whitney, who helped Selznick financially with GWTW.
If anyone thinks they know who Jimmy's date is, feel free to leave a comment! (I have no idea!)
Joan Fontaine's Memory of Olivia and Jimmy
Fishgall quotes a passage from Joan's 1979 autobiography, No Bed of Roses:
[Joan] remembered inviting her sister and Stewart to dinner to mark de Havilland's birthday (July 1, 1940 - Olivia turned 24; Jimmy was 32). "Two hours after the time they were asked for," Fontaine wrote, "Olivia and Jimmy rang our bell. When I remonstrated that the dinner as hardly palatable any longer, Olivia answered, 'It's my birthday. I can arrive whenever I like!'" Ha! Ha!
Olivia and Jimmy's 1940 romance continues...
More from the Stewart biography by Fishgall:
De Havilland was in all probability the first woman that Stewart ever seriously considered marrying. After all, she was well-bred, college educated, and refined-all qualities that he desired in a wife. He did, in fact, propose, although de Havilland would later say, "I think his offer of marriage was just a frivolous thing on his part. Jimmy wasn't ready for a wife. I guess he still had a few more wild oats to sow." The exact nature of their relationship never became public, but the Hollywood press used plenty of ink speculating on what was transpiring between the two stars, including the possibility that they might elope in the spring of 1940. Columnist Gloria Hall also reported that Warner Bros., which ad de Havilland under contract, wanted to team the actress and her new boyfriend in a picture, but the stars refused. (The only films in which they both appeared in were 1977's Airport '77 and the TV Miniseries North and South, Book II in 1986) According to the reporter, they gave as their reason that "they would be embarrassed to make love - in public." Thus, de Havilland spent the spring of 1940 making My Love Came Back and Stewart did The Mortal Storm and No Time for Comedy.
Of course in 1940 Jimmy was also busy filming a third movie - The Philadelphia Story, which finished shooting in August of 1940. Once the film wrapped, Stewart helped to organize a benefit in Houston Texas to support Great Britain, then standing alone against the forces of Nazi Germany.
Jimmy was still seeing Olivia at this time.
The benefit took place in August 1940 at the Houston Coliseum. It featured Tyrone Power, Mischa Auer, and Henry Fonda, a longtime friend of Jimmy's. In the show, Fonda and Stewart did a magic trick act together. Stewart also played accordion and Fonda the cornet. Olivia also participated in the show.
Not long before that, Olivia returned to her Hollywood home after location filming on Santa Fe Trail. Away from home, she had been bored and lonely, and missed spending time with Jimmy. The excerpt continues:
According to biographer Charles Higham, "Her only consolation (during filming) was the chance of returning to Stewart on an occasional weekend for flying lessons and romance." (Jimmy was a pilot and loved taking her on trips over southern California and over the sea) Nevertheless, the relationship between the stars had cooled. De Havilland increasingly felt Stewart's marriage proposal was pro forma, that he didn't really want to settle down. Still they continued to date for nearly another year. Then Livvy fell in love with John Huston, the director of her then current film, In This Our Life, and the relationship with Stewart came to an end. By that point, Jim was in the service. (Stewart enlisted in the Army in March 1941)