Did Frank Sinatra and Grace Kelly Have an Affair?

During the 1950s, Frank Sinatra and Grace Kelly were Hollywood royalty. Both won Oscars and attended glamorous events. They also formed a close friendship, strengthened by working together in Kelly’s final film, High Society. According to Sinatra’s former valet, however, they may have had something more than just a friendship. 

Frank Sinatra and Grace Kelly met on the set of ‘Mogambo’

When Sinatra and Ava Gardner were newly married, he flew to Kenya as a romantic gesture. She was filming Mogambo, a film about a love triangle between herself, Kelly, and Clark Gable while on a safari. While shooting, the cast and crew shared a tent, allowing Sinatra and Gardner to put their tumultuous relationship on full display. At first, Kelly was appalled by the arguing, drinking, and sex.

 “Ava is such a mess it’s unbelievable,” Vanity Fair reports that Kelly told a friend. She also wrote a letter, hinting that she wasn’t Sinatra’s biggest fan. He was notorious for his temper, particularly when he’d been drinking.

“Frank left Friday, so maybe things will easier,” she wrote, per the Independent.

As the shoot wore on, however, Kelly joined the group in their antics, though “after a few drinks she usually ended up turning pink and running into the bushes to vomit.” She also reportedly began an affair with Gable.

They had a close relationship

Several years later, Kelly appeared in her final film, High Society, alongside Sinatra. In it, he plays a reporter, one of three men vying for Kelly’s attention. This was Kelly’s final film before she married Prince Ranier III of Monaco and retired from acting. Clearly, at this point, her feelings toward Sinatra had softened. When she stepped away from Hollywood, her friendship with Sinatra remained steadfast. According to Kelly’s son, Prince Albert, Sinatra was a frequent guest at the palace in Monaco.

Sinatra’s longtime valet George Jones gave further insight into their relationship. Jones said Sinatra “dated quite a few of beautiful ladies,” he told CBS News. “They were all treated very well.”

When asked if Sinatra and Kelly had a romantic relationship, Jones replied, “He did a movie with her and he dated her, but I don’t know.”

According to him, though, any possible romance ended when Kelly married Prince Ranier III. He primarily visited Monaco on friendly visits to support her charity work. In addition, “Prince Ranier was a good friend of his.”

Frank Sinatra led a tribute to Grace Kelly on the first anniversary of her death

One year after Kelly’s death in 1982, Sinatra hosted a tribute to honor his friend.

“She’s just an angel among a lot of saints, and she belongs there,” Sinatra said, per UPI.

According to the article, Sinatra teared up as he spoke to the crowd at the service in Los Angeles. Gregory Peck, Barbara Sinatra, Cary Grant, and Karl Malden were among the mourners.

“She was a beautiful human being. She was never without strength, beauty, and dignity,” he said, adding, “She was the most incredible human being I’ve ever known. Everything she touched came alive. It is obvious Prince Rainer is a very lonely man. I think we all are, those who have known her.”

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