Controversial Hollywood Relationships With Age Gaps

Age-gap relationships have long been a Hollywood staple, with older stars often dating much younger partners. Even today, it’s common to see celebrities in relationships with people young enough to be their children—or even grandchildren. In most cases, especially in Old Hollywood, the older partner was almost always the man.

It was rare to see a woman significantly older than her romantic partner, but one notable exception was Dolores del Río and Orson Welles. The Mexican superstar was 11 years older than Welles, who first saw her on screen as a teenager and later admitted, “That’s when I fell in love with her.” They finally met at a party in 1939 and began a relationship that lasted for years before falling apart.

Compared to some Hollywood relationships, an 11-year difference seems minor. But in the Golden Age, it was far more common to see older men marrying women who, in many cases, were far too young.

Charlie Chaplin’s Marriages: A Pattern of Young Brides
Charlie Chaplin, the legendary silent film star, had a complicated history when it came to love. Born in 1889, he married four times, with three of his wives being teenagers—two of them underage.

His first wife, Mildred Harris, claimed Chaplin noticed her in a film when she was 12 and met her at 15. Though she admitted she was still very young emotionally, they began a relationship and married when she was 16, mistakenly believing she was pregnant. They divorced two years later.

His second wife, Lita Grey, met Chaplin at 12 and was pregnant at 15. Their marriage didn’t last long either. In 1932, Harris quipped to a reporter, “Too much sweet 16—that’s Charlie’s trouble.”
He almost took that advice when he married Paulette Goddard, a more mature 25, but they divorced after six years.

Chaplin’s final and longest marriage was to Oona O’Neill, daughter of playwright Eugene O’Neill. She was 18, and he was 54—just six months younger than her father. They remained together for 34 years until Chaplin’s death.

Jean Harlow and Paul Bern
Jean Harlow was Hollywood’s original blonde bombshell, captivating audiences in the early 1930s. After divorcing her first husband as her career took off, she landed the role that made her a star—1932’s Red-Headed Woman—thanks to influential MGM producer Paul Bern. The two soon became romantically involved.

Their July 2, 1932, wedding surprised many, not because of their 20-year age gap but because Bern was known for his bachelor lifestyle. The Los Angeles Times even noted the age difference, calling it a romance where “Miss Harlow, now 21, took as her husband a man considerably her senior…”.

Just two months later, on September 5, Bern was found dead in their home, an apparent suicide. But the story took a twist—police learned Bern had never divorced his first wife, Dorothy Millette, whom he still supported financially. When Millette also died by suicide shortly after, speculation swirled about whether she had a hand in his mysterious death.

Douglas Fairbanks Sr. and Sylvia Ashley
Douglas Fairbanks and Mary Pickford were Hollywood’s first power couple, dominating the silent film era as actors, producers, and co-founders of United Artists with Charlie Chaplin. They left their previous spouses to marry in 1919, but by 1931, their once-glamorous union was falling apart.

Enter Lady Sylvia Ashley, the young wife of an aristocrat. Fairbanks met her at a party and was immediately smitten. At 26, she was nearly 15 years younger than Pickford, who reportedly felt she couldn’t compete with Ashley’s beauty. For two years, Fairbanks strung Pickford along before sending a telegram from Europe saying he wasn’t coming back. Pickford leaked the message to the press and filed for divorce in 1933.

Ashley’s husband soon divorced her, naming Fairbanks as the reason. The new couple married in March 1936 when he was 52 and she was 31. Friends, including the Duchess of Argyll, claimed Fairbanks was pathologically jealous, never letting Ashley out of his sight. Despite this, they remained together until he died in 1939. Ashley later married three more times—including Clark Gable.

Humphrey Bogart and Lauren Bacall
Lauren Bacall’s Hollywood debut was nothing short of legendary—her first film role was opposite Humphrey Bogart in To Have and Have Not. When they first met, she later told Vanity Fair, “There was no clap of thunder, no lightning bolt, just a simple how-do-you-do.” But once filming began, sparks flew, and they quickly fell for each other.

Their 25-year age gap wasn’t the biggest obstacle—it was the fact that Bogart was already married. His wife, Mayo Methot, struggled with alcoholism and intense jealousy, even stabbing him once in a drunken rage. Eventually, they divorced, and Bogart and Bacall married in 1945. He was 45, she was 20, and despite their differences, Bacall later called the age gap “the most fantastic thing for me to have in my life.”

However, their marriage wasn’t always smooth. Bogart preferred a traditional wife over a working actress, which limited Bacall’s career. Both were rumored to have had emotional affairs, but they remained together until Bogart’s death from cancer in 1957, leaving Bacall a widow at just 32 years old.

Errol Flynn: His Two Wives and Underage Girls
Errol Flynn, the charming action star of old Hollywood, loved living life on the edge—both on screen and off. Known for saying, “I like my whiskey old and my women young,” he wasn’t kidding about the “young” part. The trouble was, his taste often veered into teenage territory—sometimes illegally so.

Back in 1943, two 17-year-old girls accused Flynn of rape. He beat the charges but later hinted in his autobiography that he might’ve been guilty by legal standards—though he shrugged it off, claiming everyone knew the girls wanted it. During that trial, the 34-year-old actor caught the eye of 18-year-old Nora Eddington in the courtroom. Sparks flew, and they tied the knot soon after, only to split by 1949. A year later, Flynn, then 41, said “I do” again—this time to 23-year-old Patrice Wymore.

Flynn’s wild ride ended in 1959 when he dropped dead at 50 while in Canada with his 17-year-old girlfriend, Beverly Fisher. They’d been together two years, and when a reporter asked about his thing for young girls, Flynn fired back with a crude zinger.

William Randolph Hearst and Marion Davies
In 1917, newspaper tycoon William Randolph Hearst first laid eyes on Marion Davies, a 20-year-old Broadway chorus girl performing in the Ziegfeld Follies. At 54, he was instantly captivated. According to Captain of Her Soul: The Life of Marion Davies, he courted her with lavish gifts and secret meetings, keeping their affair hidden from both his devoutly Catholic wife, Millicent, and his elderly mother—divorce was never an option. Eventually, the secret got out, and Hearst began openly living with Davies, particularly at his sprawling California estates.

Their 34-year age gap fueled Hearst’s intense jealousy. In 1925, he even hired detectives to follow Davies, reporting back on her every move. His biggest concern? Her friendship with Charlie Chaplin. At one point, he angrily broke up with her, calling Chaplin a “dirty little ignorant Cockney clown.”

Despite his possessiveness, they stayed together until Hearst died in 1951. Davies, an accomplished actress and producer, even loaned him $1 million when his empire struggled. Yet, in the end, she was barred from his funeral, a final reminder of their complicated love story.

Elizabeth Taylor and Her Many Marriages
Elizabeth Taylor’s love life was just as dramatic as her films. She famously married eight times, including twice to Richard Burton. But before the whirlwind that was Liz & Dick, she married actor Michael Wilding, her second husband.

In 1951, while working on a film together, Taylor—then just 19—actually proposed to him. According to The Life of Elizabeth Taylor, Wilding hesitated because she wasn’t legally old enough to marry without her parents’ consent. Meanwhile, Taylor tried to look older by piling on makeup. They eventually wed in 1952, when she was 20 and he was 40. Years later, Taylor admitted, “I wanted the calm and quiet and security of friendship.”

Ironically, the man she left Wilding for—producer Mike Todd—was even older. But unlike Wilding, who seemed to slow down with age, Todd’s high energy made their 23-year age gap feel irrelevant. Later in life, Taylor found herself on the other side of a May-December romance when, in 1991, she married Larry Fortensky, who was 20 years younger.

Bing Crosby and Kathryn Grant
When Bing Crosby met Kathryn Grant, he was a widower, and she was a young actress just starting in Hollywood. Their relationship took time to come together—Grant later joked that every time they planned to marry, Crosby would get a kidney stone or something equally dreadful.

Finally, in 1957, they secretly tied the knot in Las Vegas. When reporters caught wind of the wedding, Crosby threw them off by leaking a fake location hours away, allowing them to have a quiet, private ceremony. She was 23, he was 53, and as one newspaper bluntly noted, he was balding.

Despite the 30-year age gap, Grant said she never really paid attention to public opinion. “By the time we married, I knew I could survive without him, and he realized he didn’t want to survive without me,” she once said. The couple had three children and stayed together until Crosby died in 1977.

Carlo Ponti and Sophia Loren
Sophia Loren and Carlo Ponti were married from 1966 until his passing in 2007, but their love story began much earlier—and faced serious legal obstacles along the way.

They first met at a beauty contest in Rome when Loren was just 16 and Ponti, a judge, was 38. He noticed her sitting with friends, and sent her a note encouraging her to enter, and though she finished second, the real prize was the start of their relationship. “We genuinely loved each other,” Loren later said. By the time she was 19, their friendship had turned into something serious.

There was one major problem—Ponti was already married, and Italian law made divorce nearly impossible. In 1957, he tried to divorce his wife by proxy in Mexico and marry Loren the same way. But Italy didn’t recognize the divorce, only the new marriage, which technically made Ponti a bigamist. To avoid legal trouble, they had the marriage annulled. It wasn’t until 1966, after they became French citizens, that they were finally able to legally wed and live as husband and wife.

Cary Grant and Betsy Drake
By 1947, Cary Grant was 43 years old, twice divorced, and one of Hollywood’s biggest stars. When he saw Betsy Drake perform in a London play, he was instantly captivated. Fate intervened when they happened to take the same ship back to the U.S., leading to conversations that quickly turned into romance. Despite their 19-year age gap, they married two years later.

Their relationship had its ups and downs—Grant attempted (and failed) to retire from Hollywood, and Drake introduced him to LSD. But by 1956, things were unraveling. While filming in Europe, Grant fell for 22-year-old Sophia Loren, even proposing—despite both of them being involved with other people. Meanwhile, when Drake survived a deadly ocean liner collision, Grant didn’t even leave set to check on her.

They separated soon after, but their divorce wasn’t finalized until 1962. Despite it all, they remained lifelong friends, with Grant later saying, “She wanted to help humanity, to help others help themselves.”

John Houston and Enrica Soma
When Anjelica Huston was asked about May-December relationships, she admitted it depends on the couple. She had a front-row seat to one of Hollywood’s most complex—her parents, director John Huston and Enrica Soma.

They first met when Soma was just 14 at her father’s speakeasy. Huston, already an established filmmaker, offered to take her to the ballet—a plan that, thankfully, never materialized. They reconnected years later at a dinner party, and by then, Soma was 18. Huston, meanwhile, was married—but that didn’t stop him from getting his young mistress pregnant. On February 10, 1950, he had a busy day in Mexico—divorcing his third wife and immediately marrying Soma. She was 20, he was 45.

Their marriage was far from conventional. Soma later had a third child, Allegra, whom she raised as Huston’s daughter, only for Allegra to learn at age 12 that her real father was an English lord. Despite their complicated relationship, Huston and Soma never divorced. She passed away in 1969 at just 39 years old.

Vincente Minnelli and Judy Garland
Judy Garland was thrown into Hollywood stardom as a teenager, and by 21, she was already married—to composer David Rose, who was 12 years older. But her heart wasn’t always loyal—she had a longtime interest in producer Joe Mankiewicz, who was also older (and married). Then came Meet Me in St. Louis, directed by Vincente Minnelli, the man who would become her second husband—though not right away.

At first, Minnelli drove Garland crazy with his perfectionism, demanding take after take beyond what she was used to. While she pursued a romance with her co-star, she and Minnelli began having casual dinners with cast members. One night, it was just the two of them, and their connection deepened. However, Garland was still married, rekindling her affair with Mankiewicz, and ignoring rumors that Minnelli was gay.

In June 1945, just a week after her divorce, Garland (23) married Minnelli (42). They soon had a daughter Liza Minnelli, but unresolved issues—including Garland’s affair with Orson Welles—doomed the marriage. They divorced in 1951.

John Wayne and Pilar Pallete
John Wayne and Pilar Pallete had a romance that started in Los Angeles, but their first meeting was far more dramatic—it happened in a jungle in Peru in 1952. At the time, Pallete was a young actress filming a fiery dance scene, and Wayne was immediately impressed. But he was also stuck in a toxic marriage with his second wife, Esperanza Baur, with both partners accusing each other of infidelity and abuse.

As Wayne’s messy divorce dragged on, Pallete became pregnant and ultimately chose to have an abortion, partly to protect his reputation. They finally married in 1954, when he was 47 and she was 24. Pallete later told The Los Angeles Times that despite the 23-year age gap, Wayne felt youthful and full of energy, loving to dance, water ski, and enjoy life.

Over their 25-year marriage, they had three children, but their relationship wasn’t without issues. By the end, they lived apart for six years, though they never officially divorced. When Wayne passed in 1979, Pallete was left out of his will, though his lawyers clarified that she had already received a settlement after their separation.

Jerry Lee Lewis and Myra Gale Lewis
Jerry Lee Lewis wasn’t just a rock ‘n’ roll pioneer—he also dabbled in Hollywood, making a cameo in the 1958 film High School Confidential! While the movie itself was forgettable, many saw Lewis as a rising star, even a potential rival to Elvis Presley, which could have led to a movie career of his own.

But that same year, his career imploded. When he arrived in the U.K. for a European tour, a reporter noticed a very young girl traveling with him. When asked, Lewis casually introduced her as his 15-year-old wife, Myra Gale Brown. The British public was outraged—but what they didn’t yet know was that she was actually 13, his second cousin and that he wasn’t legally divorced from his first wife, making him a bigamist.

The scandal ended his Hollywood hopes overnight, and his music career crashed. It took him a decade to stage a comeback. Meanwhile, his marriage to Myra lasted until 1970, when she filed for divorce, citing abuse and infidelity.