Kelly Stewart Harcourt always admired the marriage of her parents, Jimmy Stewart and Gloria Stewart (née McLean). “They shared a sense of humor and had a great respect for each other,” she exclusively tells Closer. “My mother was a really good sport and was really beautiful. I think my father was waiting for the right woman.”

The It’s a Wonderful Life star became the ultimate family man after he wed Gloria in 1949, but in the years before meeting her, he romanced a who’s who of Golden Age actresses and even had his heartbroken. Olivia de Havilland, Ginger Rogers, Norma Shearer and especially, Marlene Dietrich, all enjoyed young Jimmy’s attention. But the one woman he desired most, Margaret Sullavan, his costar in 1940’s The Shop Around the Corner, would turn his world upside down.

jimmy-stewarts-dating-history-before-marrying-wife-gloria
Anonymous/AP/Shutterstock

As a young Broadway actor freshly arrived in Hollywood in the mid-1930s, Jimmy needed to prove himself to his new boss, MGM titan Louis B.Mayer. “Because Jimmy was so shy, they thought he was gay,” Marc Eliot, author of Jimmy Stewart: A Biography, explains in Closer‘s latest issue, on newsstands now. So, Mayer had Jimmy “tested.”

“He made him go to the studio house — every studio in those days had houses made up of chorus girls and starlets who were happy to do a ‘favor’ for the head of the studio,” Eliot explains, revealing Jimmy spent time with one of the girls and aced the test. “He saved his career that way.”

The studio began setting Jimmy up on dates with some of its most beautiful stars, but these camera-ready romances were hit or miss. “Jimmy and Ginger Rogers were not a good mix. The only thing they had in common was politics — both of them were highly conservative,” Eliot says. He had better chemistry with Loretta Young, but she was more serious than Jimmy. “She wanted to get married,” Eliot continues, “but there was nothing about her that could keep him interested.”

In 1937, actress Norma Shearer, the widow of studio honcho Irving Thalberg, took a shine to Jimmy, who was six years her junior. She ferried Jimmy around in a limousine and gave him a diamond cigarette case, but he quickly tired of being put on display. “I did everything to hint that I was not her possession,” Jimmy once said.

Another larger-than-life star, Marlene Dietrich, briefly made Jimmy her own when they costarred in 1939’s Destry Rides Again. “She locked Jimmy in her dressing room and seduced him,” says Eliot. But after the filming ended, so did their affair. “Most of her costars got over her quickly, but Jimmy didn’t.”

jimmy-stewarts-dating-history-before-marrying-wife-gloria
AP/Shutterstock

Jimmy once called his dating life “a lot of fun,” but the plainspoken young man from Pennsylvania lost his heart to more than just Marlene. “He could be the master of unrequited love,” explains Eliot, who points to Jimmy’s failed attempts to get Olivia de Havilland to marry him. “Jimmy wasn’t ready for a wife,” said Olivia, who called their relationship “a sort of high school prewar romance.”

Jimmy’s biggest unrequited love would be for Margaret Sullavan, his costar in four films. The pair met years earlier doing summer stock. “She was very pretty, petite and sexy,” describes Eliot. Jimmy asked her out in the “longest, slowest, shyest but most sincere invitation,” Margaret once recalled. But her heart had already been claimed by another member of their company, Jimmy’s best friend, Henry Fonda. “Jimmy was in love with Margaret, but she was more into a bad boy like Henry,” Eliot shares.

Henry and Margaret would marry in 1931 and divorce only months later. She remained close to Jimmy, and although their relationship never turned romantic, Margaret helped him launch his film career and gave him insight into what he wanted in a partner. “She was his best acting teacher,” says Eliot. “She also really taught him who he was — and who he wasn’t. And that set him up for the way his love life went.”

But there were still other false starts. Jimmy fell for Donna Reed, his wife in 1946’s It’s a Wonderful Life. “He was crazy about her,” Eliot dishes. “But she was married, and neither one was the kind of person who would act on it.”

He finally met Gloria McLean at a dinner party in the summer of 1948 and was immediately taken with her beauty, sweet nature and humor. The couple wed the following year, and their twins, Kelly and Judy, were born in 1951. Along with Gloria’s sons, Ronald and Michael, they created a happy, blended family that endured for the rest of their lives. “I’ve had so many blessings and good fortune. Gloria and the children continue to bring me enormous pleasure,” said Jimmy in 1985, 12 years before his death. “On the whole, it’s been a darn wonderful life.”

jimmy-stewarts-dating-history-before-marrying-wife-gloria