Old Hollywood Stars Who Had Sizable Age Gaps In Their Relationships

Old Hollywood was a glamorous place. And part of the fabled old-world charm it is eulogized for today came from the element of scandal that often characterized it. Of course, the early 20th century was guided by stricter social conventions, so most things that seem natural in showbiz now were inherently sensational back then. One such recurring theme during the Golden Age was the age-gap romance.  

It wasn't hard to come by celebrity pairs separated in age by many years, sometimes even decades — with the dynamic typically lopsided with a senior male partner. Questionably enough, many of these romances bloomed when the women involved were barely out of their teens. While some couples managed to happily see their relationships through till the end despite the age chasm, many crumbled midway under the pressures of orthodoxy or infidelity.  

Here are stories of some old Hollywood stars who had sizable age gaps in their relationships and how they navigated them.

Humphrey Bogart and Lauren Bacall's relationship had all the makings of a quintessential Golden Age love story: a fateful meeting, a forbidden romance, a string of roadblocks, and eventually, a happily ever after. Bacall met Bogart while making her debut in the 1944 war film "To Have and To Have Not" opposite him, and it didn't take long for sparks to fly. Their budding love affair, in true cinematic fashion, wasn't without its hurdles. 

For starters, Bogart was married to actress Mayo Methot at the time. Then there was also the fact that he was 25 years older than Bacall. The controversial circumstances didn't seem to spook either party, and by 1945, after Bogart's divorce, they tied the knot. Not least because they also successfully co-starred in classics like "The Big Sleep" and "Dark Passage," Bogart and Bacall quickly attained power-couple status. 

Behind closed doors, however, their picture-perfect relationship was dominated by Bogart's conservative outlook on marriage. As Bacall once told People: "Bogie was an old-fashioned man. He kidded that a woman's place was in the home, but he was only half kidding." Though she had to put her career second to her marriage, Bacall spoke fondly of Bogart, with whom she had two children and stayed with until his death in 1957. 

In what was one of the most alarming age-gap relationships in Hollywood history, showbiz icon Bing Crosby and his actress wife Kathryn Grant were separated by 30 whole years. The generational divide, however, proved of little consequence to the longevity of their relationship. The two first crossed paths on the Paramount lot in 1953 and, as Grant recalled for PBS, Crosby lost no time in making a move. "He invited me for a cup of tea ... and I looked into his big blue eyes and about 15 minutes later, I realized I was in love." 

Unlike many male stars from the Golden Age who were undeterred in their pursuits of younger women, Crosby apparently expressed some reservations about marrying a woman 30 years his junior. "[H]e thought I was too young for him. And maybe I was. I thought I was very grown," Grant, who was only 19 when she met Crosby, noted. That said, Crosby was hardly a saint. According to The New York Times, his romantic escapades continued outside his courtship with Grant, and after their marriage in 1957, his conservative views on homebound wives came unabashedly to the fore. Regardless of Grant's opinion that Crosby was "a male chauvinist pig," she remained with him until his death in 1977.

Elizabeth Taylor was married a stunning total of eight times, with each of her relationships making more headlines than the last. Her second wedding, to actor Michael Wilding, was one such sensation. And while in the annals of Taylor's colorful love life it often tends to go overlooked, some aspects of it were definitely of note. For one, Wilding was 20 years Taylor's senior — a fact that didn't faze the "Cleopatra" star. If anything, it was a source of appeal for her. 

"When I was first divorced, I was 18 and I had only been married nine months. I was very naive and really totally crushed. ... With Michael Wilding, who was much older than I was, I wanted the calm and quiet and security of friendship," she told Life magazine (via Google Books).

They said "I do" in a low-key ceremony in London in 1952 and eventually welcomed two children together. Picture-perfect as it seemed, the marriage apparently left Wilding unmoored and insecure about his own acting career, which was not nearly as successful as his wife's. They remained husband and wife for five years before parting ways in 1957. 

Before he married budding actress Patrice Wymore, Errol Flynn had already accrued a bit of a reputation in Hollywood as an insatiable Casanova. The "Captain Blood" star enjoyed a notoriously colorful lifestyle marked by a penchant for substances, a string of lovers, and a constant element of scandal. So when he courted Wymore, who was 17 years his junior, it was controversial but not totally out of character for him. The two met while co-starring in the 1950 film "Rocky Mountain" and got married that same year. 

"Patrice typified everything that I was not," Flynn wrote in his memoir "My Wicked, Wicked Ways," which contained several glimpses of his seemingly fulfilling third marriage (via The Sydney Morning Herald). "She could cook Indian curry, she could dance, she could sing, she was reserved, she had beauty, dignity ... homebody qualities that go toward making a sensible and lasting marriage." In spite of the qualities he saw in her, Flynn couldn't completely shake off his playboy instincts and apparently continued to pursue the attentions of other women outside his marriage. Though they eventually lived separate lives, the pair remained wedded until Flynn's death in 1959. 

Though it lasted only two years, Frank Sinatra and Mia Farrow's marriage continues to be a momentous chapter in Hollywood history. A 31-year age difference stood between the two film legends when they first crossed paths in 1964 on the 20th Century Fox studio lot. The sparks were seemingly heady enough to override any concerns the couple may have had about their wide age gap, and at the age of 21, Farrow married the "My Way" singer. 

While it was the third attempt at marriage for 50-year-old Sinatra, who was infamous for his roving eye, young Farrow was experiencing marital life only for the first time. It was a union doomed from the start. "I was less mature than any other 19-year-old I've ever known. Poor Frank, saddled with such a child," Farrow recalled for The Guardian. It didn't help that Sinatra, like several of his conservatively minded contemporaries, was discouraging of Farrow's showbiz career. 

In fact, it was her rebellion against this that ended their marriage. When despite Sinatra's objections, Farrow refused to abandon her role in "Rosemary's Baby" — which ultimately proved her big breakthrough — the mercurial singer had divorce papers sent to her set. Notwithstanding their turbulent marriage, Farrow and Sinatra remained friends until the latter's death in 1998.

In her rather colorful lifetime, Judy Garland had a total of five husbands, out of which director Vincente Minnelli was perhaps the most consequential in the larger picture of Hollywood history. This distinction, of course, stemmed in large part from the daughter they welcomed together — the future stage and screen legend the world came to know and adore as Liza Minnelli. But Garland and Minnelli's union was of note long before they became parents. The massive 19-year age gap that separated them raised eyebrows back in the 1940s, when they became an item after meeting on the set of "Meet Me in St. Louis." 

Age wasn't the only obstacle that stood to hinder their love story. There was the issue that Garland was still trying to obtain a divorce from her (also much older) ex-husband and, as Vanity Fair noted, the open secret that Minnelli might have been queer. Bypassing it all, Garland and Minnelli tied the knot in 1945. That hardly marked the end of their troubles. The pressures on Garland's notoriously troubled mental health and competitive resentment unfolding in the face of Minnelli's growing relationship with her home studio of MGM strained their marriage until it eventually came apart in 1950. As Liza Minnelli later attested to Interview magazine: "[T]hey didn't really like each other." 

A bona fide Golden Age screen siren, Sophia Loren was desired by millions who saw her as the ultimate embodiment of sensuous glamor. But she had eyes for only one man (more or less) for much of her life: Carlo Ponti. She met the Italian producer at 16, when he was 39 and already married, but very smitten with the teen beauty queen. Loren took to Ponti, too — not just as a romantic interest but also a father figure, comprehensibly because of the 23-year age gap between them. 

"He gave me a rootedness and stability that kept me grounded while the world around me seemed to swirl dizzyingly," she wrote in her memoir "Yesterday, Today, Tomorrow: My Life" (via Vanity Fair). The romance that eventually transpired between Loren and Ponti carried an element of scandal in conservative Italy, where the sanctity of marriage was protected by the illegality of divorce up until 1970. 

From facing exile to public judgment, and even an unsuccessful proxy marriage, the couple weathered it all. That is until 1966, when they became French citizens so they could safely and legally marry. Though there are tales of internal strain in their marriage, the duo lived together as husband and wife until Ponti's death in 2007. 

Marilyn Monroe's romance with baseball icon Joe DiMaggio was legendary for more than one reason. Their 12-year age gap drew its fair share of attention, for starters. Monroe was 25 when she first met the New York Yankees star, and two years of dating later, they tied the knot in a small, fanfare-free ceremony in 1954. For all the star power that their high-profile marriage packed, it infamously stood on rocky foundations right from the beginning. One was a baseball celebrity and the other was a globe-trotting film star, and so schedules inevitably clashed. Presumably, that might have been one of their lesser problems in the context of their reportedly abusive domestic life. 

DiMaggio, it is said, didn't take well to his wife's growing superstardom and showbiz commitments, especially those that leaned into her sex symbol persona. Monroe's seminal skirt-blowing scene in "The Seven Year Itch," for instance, sparked one such moment of opposition from DiMaggio, who allegedly became so enraged that he physically assaulted the actor (via History). His insecurities were also evident in the way Monroe described him: "He wants to cut me off completely from my whole world of motion pictures." The couple divorced after just nine months of marriage, with Monroe citing mental cruelty. 

Love was a recurring theme in Cary Grant's life, just one that he didn't seem to be able to hold down for too long with any single person. The closest he came to committing to a long-term relationship was with his third wife Betsy Drake, to whom he was married for 13 years. Their first meeting happened fatefully aboard the RMS Queen Mary in 1947, and amid the romantic setting of the open seas, a romance blossomed. 

Their 19-year age gap hardly seemed like an obstacle at the time, given Grant's record of pursuing younger women. And so, in 1949, the actor pair said their "I dos" and set out to build a life together. Their partnership seemed steady for a while; Drake had found an inroad into Hollywood films beside her superstar husband, while Grant drew from her knowledge of psychedelic therapy. 

But Golden Age debonair that he was, Grant could resist romantic distractions outside his marriage for only so long. On the set of "The Pride and the Passion" in the '50s, Grant got involved with Sophia Loren. Besides evolving into one of old Hollywood's most scandalous affairs, the pairing marked the beginning of the end of Grant's marriage to Drake. They divorced in 1962. 

Legendary filmmaker John Huston had five marriages in his lifetime, the most talked-about of which was his fourth, to socialite Enrica Soma. Not only was this because it was crucial to the expansion of the Huston Hollywood empire, with the birth of acting greats like Anjelica Huston, but it was also because of its wide age gap. Soma was only 20 when she tied the knot with the then-43-year-old Huston, who had pursued the young starlet despite already being married at the time. 

Idyllically as it began, with a home in the Irish countryside and children to complete the family, the marriage wasn't built to last. Notorious for his lifestyle of extravagant excess, Huston soon crossed the line out of monogamy and into other relationships outside his marriage. Soma, too, followed suit. "Both my parents strayed during the marriage, and I think there was a sense, certainly on my father's part, that he was simply doing what came naturally to him," Anjelica Huston wrote in her memoir (via Vanity Fair). 

The pair separated in the early 1960s, with Soma moving to England with her children and Huston continuing to live life in the Hollywood fast lane. Though their relationship crumbled, the two legally remained husband and wife until Soma's death in 1969 following a car accident in France. 

Much like her on-screen firebrand persona, Jean Harlow wasn't one to abide by convention in real life. So sometime during the making of the 1930 film "Hell's Angels," when she met MGM producer Paul Bern, their 21-year age gap didn't daunt her from pursuing a relationship with him. The whole affair wasn't just romantically beneficial for Harlow; it was also conducive to professional advantages. Bern was widely credited with breathing life into Harlow's faltering career and catapulting her to mainstream stardom by backing her rise as an MGM star. 

Bern's support for Harlow was hardly surprising, given his reputation as "Hollywood's Father Confessor" and his record of helping struggling artists. What apparently did come as a bit of a jolt was that he decided to tie the knot with this particular protégé. In 1932, when Harlow was 21, she got married to Bern. Tragically, their marriage was cut short just two months later by Bern's mysterious suicide. The case quickly became a sensation in light of an intriguing suicide note, talk of foul play, Harlow's speculated role in all of it, and the death of Bern's ex-wife. Five years later, Harlow also sadly died of kidney failure. She was 26.

For all the joy he brought to the world, Charlie Chaplin's personal life comprised many dark chapters — his controversial marriage to Oona O'Neill among them. The daughter of writers Eugene O'Neill and Agnes Boulton, O'Neill was only 18 when she tied the knot with the legendary comedian, who was 54 years old at the time. Though pursuing significantly younger women wasn't unusual for Chaplin — who had been married thrice before, including (troublingly) to teenage girls — their union in 1943 raised further eyebrows. 

According to Chaplin's official website, however, the wide age gap between the Hollywood pair didn't take away from the fact that "they had both found their soul mates." It was a sentiment Chaplin echoed, gushing about his happy married life with O'Neill in his 1964 autobiography: "For the last 20 years I have known what happiness means. ... As I live with Oona, the depth and beauty of her character are a continual revelation to me." Sure enough, the Hollywood pair seemingly proved the skepticism surrounding their age-gap marriage wrong and reveled in domestic bliss for 34 years until Chaplin's death in 1977.

Mae West and Paul Novak never officially married, but they shared a love just as enduring as long-term companions, if not better. A rare exhibit as far as successful age-gap relationships go, West and Novak were separated by a seemingly inconsequential 30-year divide, with the "She Done Him Wrong" star forming the older half of the couple — a scandalous subversion of the typical dynamic in May-December love stories. Novak originally came into West's life as a background performer — one of several musclemen she was girdled by — and eventually, after years of professional loyalty to her, evolved into her bodyguard, caretaker, and lover all rolled into one. 

For about 26 years — from when they met in the 1950s right up until West's death in 1980 — Novak remained a steady plus-one to the showbiz star, accompanying her everywhere from high-profile Hollywood events to her shows. "How did she ever pick me? Me, just a wrestler and a roustabout," Novak reportedly once exclaimed (via Los Angeles Times). The epilogue of their love story, however, wasn't as charming, with Novak slapping lawsuits on West's estate after it shockingly excluded him from her will.