Unlike many of his fellow Hollywood luminaries, James Stewart’s private life was surprisingly sedate for such a huge star.

His earliest public relationship was with the actress Margaret Sullivan, whom he reportedly had fallen head over heels in love with while the two worked together in the theater. But she saw Stewart as more of a friend and felt more like his mentor than his romantic match, so the relationship never got off the ground.

A string of brief and ill-matched relationships ensued throughout the 1930s and early 1940s, in which Stewart dated several of Hollywood’s biggest female stars—Ginger Rogers, Norma Shearer, and Loretta Young among them. But again, none of them worked out and Stewart remained (in the words of gossip columnist Hedda Hopper) the “Great American Bachelor.”

All that changed—or, at least, had the potential to—in 1942 when Stewart became romantically linked with the singer and actress Dinah Shore. At the time, Stewart was serving in the US military, and Shore was performing at the Hollywood Canteen, a renowned club on Cahuenga Boulevard in Los Angeles, that was a frequent haunt of US servicemen.

The pair clicked instantly and began a year-long relationship that culminated in them driving to Las Vegas in 1943 to marry. On the journey there, however, a panicking Stewart suddenly suffered cold feet and called the entire wedding off. The relationship ultimately crumbled, and the Great American Bachelor was back on the market.

Stewart’s luck finally turned around when a chance encounter with the actress Gloria Hatrick McLean at a Christmas party in 1947 led to the couple marrying on May 22, 1949. Hollywood’s perennial bachelor had finally been snapped up at the age of 41. The couple remained together for the next 45 years until Gloria’s death in 1994.