Cary Grant’s life in the public eye wasn’t complete without a few public romances.
During his Hollywood acting career, the Oscar nominee received rave reviews for his roles in Penny Serenade and None But the Lonely Heart.
But away from the cameras, Grant made headlines for his dating life, which resulted in five different marriages.
One of Grant’s ex-wives, Dyan Cannon, recently made headlines when she opened up about juggling suitors at 88 years old. When People asked her in April 2025 if she is dating anyone, she responded, “Of course.”
“Somebody very special,” she continued before adding, “Several special [people]. … I have friends with benefits, yes.”
While Cannon has also been linked to the late Tonight Show host Johnny Carson, the actress made it clear that she isn’t done searching for a partner.
“He was a special man,” she told the publication. “I’ve known a lot of special men. And there’s more to come.”
Keep reading to learn more about Grant’s dating history and the ladies who caught his attention and heart.
Barbara Harris
In 1981 — when Grant was 77 and Harris was 30 — the couple got married. They remained together until Grant died from a stroke in 1986.
After his passing, Harris reportedly became the sole heir to Grant’s estate and money, which she split with her stepdaughter, Jennifer.
Dylan Cannon
In July 1965, Grant’s life changed forever when the then 61-year-old married Cannon, who was 28, in Las Vegas.
They welcomed their first child, Jennifer, one year later but split after three years of marriage.
In her 2012 memoir titled Dear Cary, My Life With Cary Grant, Cannon reflected on her love story.
“We met, and it was electric,” she wrote via Woman’s World. “But my little voice said, ‘Don’t go there, he’s been married several times. Do not go there.’ I really expected him to make me happy. … After all, he was Cary Grant. I made a god out of him in my thinking, and the poor guy had things to work out, like we all do.”
Betsy Drake
Before getting married on Christmas Day in 1949, Drake and Grant fell in love after meeting on the Queen Mary.
Despite a 20-year age difference — he was 45 at the time of their marriage while she was 26 — the pair experienced a long union that lasted until 1962.
They also were able to share the screen together when they starred opposite each other in films like Every Girl Should Be Married and Room for One More.
Barbara Hutton
During an ocean voyage from New York to England in 1939, Grant met Hutton. The philanthropist and socialite married the actor in 1942 but divorced three years later.
“The trouble wasn’t her,” Grant once told the Washington Post. “People just can’t disassociate her from her money, and they act like idiots around her.”
While the love story didn’t have a happily ever after, Hutton said she considered Grant “the husband I loved the most.”
Virginia Cherrill
After meeting at the premiere of Blonde Venus in 1932, the two actors hit it off and decided to get married two years later.
They experienced a romantic wedding ceremony in London before honeymooning in Rome. After less than two years of marriage, however, the couple called it quits with Cherrill alleging domestic abuse in her divorce petition.
“I doubt if either of us was relaxed enough to trust what we had,” Grant reportedly said about the split. “My possessiveness and fear of losing her brought about the very thing I had feared: the loss of her.”
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