Olivia De Havilland's Loves: A Journey Through Hollywood Romance

Mrs. Wilhelmine Deckow PhD 19 Jun 2025

When we speak of Hollywood's Golden Age, certain names immediately conjure images of unparalleled glamour, talent, and intrigue. Among them, Olivia de Havilland stands as an icon, a woman whose career spanned decades and whose personal life, particularly her relationships, captivated the public. From her early days as a rising star to her later years as a revered centenarian, Olivia de Havilland's romantic entanglements and familial bonds were as dramatic and compelling as any of her on-screen roles.

This article delves into the fascinating world of Olivia de Havilland relationships, exploring the famous men she dated, the marriages she entered, and the legendary sibling rivalry that defined much of her public narrative. If you're wondering who has Olivia de Havilland dated, then you've come to the right place to uncover the romantic history of one of cinema's most accomplished and alluring figures.

Biography of Olivia de Havilland
Personal Data & Biodata
The Early Years: Screen Debut and Rising Stardom
Olivia de Havilland's Famous Romances: A Star-Studded List
Marriages: A Look at Her Committed Relationships
- Marcus Aurelius Goodrich: The First Union
- Pierre Galante: Her Second Chapter
The Legendary Sibling Rivalry: Olivia de Havilland and Joan Fontaine
Beyond Romance: Her Enduring Legacy
Conclusion: A Life Lived Fully

Biography of Olivia de Havilland

British actress Olivia Mary de Havilland was born on July 1st, 1916, in Tokyo, Japan. Her life, spanning an incredible 104 years, was a testament to resilience, talent, and an unwavering spirit. She passed away on July 25th, 2020, in Paris, France, leaving behind an unparalleled legacy in cinema. Olivia de Havilland was one of Hollywood’s most iconic figures, remembered not just for her captivating performances but also for her pivotal role in challenging the studio system, a battle that forever changed the landscape for actors.

She is most remembered for her portrayal of Melanie Hamilton in the epic film Gone with the Wind (1939), a role that earned her an Academy Award nomination. However, her career was far more extensive, encompassing a diverse range of characters and collaborations with some of the industry's biggest names. Her journey through Hollywood was marked by both professional triumphs and a deeply personal life that often intersected with the public eye, particularly concerning Olivia de Havilland relationships.

Personal Data & Biodata

Attribute	Detail
Full Name	Olivia Mary de Havilland
Born	July 1, 1916
Birthplace	Tokyo, Japan
Died	July 25, 2020 (aged 104)
Place of Death	Paris, France
Occupation	Actress
Notable Role	Melanie Hamilton in Gone with the Wind
Siblings	Joan Fontaine (sister)
Marriages	Twice (Marcus Aurelius Goodrich, Pierre Galante)

The Early Years: Screen Debut and Rising Stardom

Olivia de Havilland's entry into the world of film was almost serendipitous. She made her screen debut in Max Reinhardt's A Midsummer Night's Dream (1935), a fantastical adaptation filmed at Warner Brothers Studios from December 19, 1934, to March 9, 1935. This early role quickly established her as a fresh face in Hollywood, paving the way for a contract with Warner Bros. and a string of successful films. It was during these formative years that she began to navigate the complex social landscape of the film industry, leading to her first encounters with some of the most prominent figures of her time.

Her natural beauty, coupled with a nuanced acting style, quickly endeared her to audiences and filmmakers alike. As her star rose, so did the public's interest in her personal life, especially her romantic connections. Accomplished and alluring, Olivia de Havilland dated her share of Hollywood's most dashing power players at the height of her career, setting the stage for the captivating history of Olivia de Havilland relationships that would unfold over the decades.

Olivia de Havilland's Famous Romances: A Star-Studded List

Olivia de Havilland's romantic life was as storied as her filmography. She was romantically involved with some famous Hollywood actors and influential figures, creating a fascinating tapestry of connections. This list features Olivia de Havilland's notable romantic interests, offering a glimpse into the heart of a woman who was both fiercely independent and deeply passionate.

Errol Flynn: The Iconic Onscreen Chemistry

Perhaps the most famous of Olivia de Havilland relationships was her captivating partnership with Errol Flynn. Their onscreen romances were some of the best classic Hollywood had to offer, captivating audiences with their undeniable chemistry in films like Captain Blood (1935), The Adventures of Robin Hood (1938), and Dodge City (1939). Their pairing was so potent that it fueled widespread speculation about a real-life romance.

While their on-screen passion was legendary, their off-screen relationship remained complex and largely unconfirmed by de Havilland for many years. However, it is widely reported that Errol Flynn and Olivia de Havilland had an encounter in 1937, suggesting that their connection extended beyond the silver screen. Olivia herself later spoke with a certain fondness and regret about their unfulfilled romance, acknowledging the deep affection she held for him. Their dynamic was a cornerstone of their respective careers, making them one of Hollywood's most beloved duos.

James Stewart: A Gentleman's Affair

Another prominent figure in Olivia de Havilland's romantic history was the beloved actor James Stewart. Known for his wholesome, everyman persona, Stewart was a different kind of leading man than the swashbuckling Flynn. Their relationship was reportedly more understated and earnest, reflecting Stewart's own reserved nature. While specific details of their romance are less publicized than her connection with Flynn, their involvement was a known part of Hollywood's social circles, highlighting Olivia's appeal to a diverse range of leading men.

John Huston & Howard Hughes: Powerful Connections

Olivia de Havilland also opened up to people about her past relationships with formidable figures like director John Huston and eccentric billionaire Howard Hughes. These were relationships that connected her not just to fellow actors but to the powerful architects of the film industry itself. Her romance with John Huston, a brilliant but notoriously complex director, reportedly involved deep intellectual and artistic connection. It was a relationship that likely challenged and stimulated her, reflecting her own intelligent and independent spirit.

Her involvement with Howard Hughes, the aviation magnate and film producer, placed her within the orbit of immense wealth and influence. Hughes was known for his intense and often controlling nature, and his relationships with Hollywood stars were frequently dramatic. Olivia's ability to navigate such powerful personalities speaks volumes about her own strength and character. These relationships underscore that accomplished and alluring, Olivia de Havilland dated her share of Hollywood's most dashing power players, reflecting her status at the pinnacle of the industry.

Other Dashing Power Players

Beyond these well-documented relationships, Olivia de Havilland's allure meant she was frequently courted by other prominent figures in Hollywood. At the height of her career, she was a highly sought-after presence, and her romantic life was often the subject of public fascination. While specific names beyond those mentioned are less frequently highlighted, it's clear that her circle of admirers included many of the era's most eligible and influential men. Her ability to attract and engage with such a diverse array of personalities further cemented her image as a captivating and desirable woman, whose Olivia de Havilland relationships were always of great interest.

Marriages: A Look at Her Committed Relationships

While Olivia de Havilland dated many famous men, she also entered into two marriages during her lifetime, seeking deeper, more committed bonds. These relationships offered different chapters in her personal journey, away from the often fleeting romances of her early career.

Marcus Aurelius Goodrich: The First Union

Olivia de Havilland was married twice before her death. She first married American playwright Marcus Aurelius Goodrich in 1946. Goodrich was known for writing the novel “Delilah.” Their union brought a different dynamic to her life, moving away from the high-profile Hollywood romances. The marriage, however, was not without its challenges and ultimately concluded in divorce in 1953. Despite its end, this marriage marked a significant step in Olivia's personal life, as she embraced the role of wife and mother, welcoming her son, Benjamin Goodrich, during this period.

Pierre Galante: Her Second Chapter

Her second marriage was to French journalist and editor Pierre Galante in 1955. This union saw Olivia largely relocate to Paris, France, a city she would call home for the remainder of her long life. With Galante, she had a daughter, Gisèle. This marriage represented a shift in her life, embracing a more international existence and a different cultural landscape. While this marriage also eventually ended in divorce in 1979, the bond of family remained strong, and she continued to reside in Paris, maintaining a close relationship with her daughter. These marriages provided stability and family life amidst her enduring fame, showcasing another dimension of Olivia de Havilland relationships.

The Legendary Sibling Rivalry: Olivia de Havilland and Joan Fontaine

Beyond her romantic entanglements, one of the most enduring and talked-about Olivia de Havilland relationships was her complex and often tumultuous bond with her younger sister, Joan Fontaine. It's one of the most legendary rivalries in Hollywood, a feud that spanned decades and captivated the public's imagination. Two sisters, born 15 months apart, who began tormenting each other almost from the time they could talk, according to Entertainment Weekly.

The rivalry intensified as both sisters pursued acting careers, often competing for similar roles and accolades. A particularly famous incident occurred when Olivia de Havilland famously rejected her sister Joan Fontaine's congratulations after winning an Oscar for Best Actress in 1946 for To Each His Own, a moment captured by photographers and etched into Hollywood lore. This public snub underscored the deep-seated animosity that had festered between them for years.

Olivia addressed her relationship with Joan, saying, "A feud implies continuing hostile conduct between two." This statement, while seemingly downplaying the conflict, hinted at the profound and often painful nature of their estrangement. The passing of their mother in 1975 did little to bridge the chasm between them. For three quarters of a century, the supposed feud between sisters Olivia de Havilland and Joan Fontaine was the stuff of tabloid dreams, a fascinating and tragic subplot to their otherwise illustrious careers. Despite their personal animosity, both achieved immense success, forever linking their names in the annals of Hollywood history, a testament to the powerful, albeit strained, Olivia de Havilland relationships with her family.

Beyond Romance: Her Enduring Legacy

While Olivia de Havilland relationships, both romantic and familial, were a significant part of her public persona, her legacy extends far beyond them. She was a trailblazer who courageously sued Warner Bros. in 1943, challenging the restrictive studio contract system. Her victory, known as the "De Havilland Law," freed actors from perpetual studio control, granting them greater artistic freedom and fairer terms. This act of defiance solidified her as a champion for actors' rights and demonstrated her formidable will.

Her career highlights include two Academy Awards for Best Actress, for To Each His Own (1946) and The Heiress (1949), showcasing her incredible range and depth as an actress. All things being equal, Olivia de Havilland turned 100 in 2016, and her centennial was celebrated globally, a testament to her enduring impact and the respect she commanded. Her life was a masterclass in longevity, grace, and an unwavering commitment to her craft and principles.

Conclusion: A Life Lived Fully

Olivia de Havilland's life was a rich tapestry woven with threads of cinematic brilliance, personal triumphs, and complex human connections. From her captivating onscreen partnerships with Errol Flynn to her enduring marriages and the legendary rivalry with her sister, Olivia de Havilland relationships were always at the heart of her public narrative. She navigated the glittering yet often challenging world of Hollywood with remarkable resilience, leaving an indelible mark not only through her performances but also through her courageous fight for artists' rights.

Her story serves as a compelling reminder that behind the silver screen glamour lies a life rich with human experience – love, heartbreak, ambition, and family strife. As we reflect on her incredible journey, it's clear that Olivia de Havilland was more than just an actress; she was a force of nature whose life, including her intricate relationships, continues to fascinate and inspire. We hope this exploration has provided you with a comprehensive insight into the romantic and familial world of this extraordinary Hollywood legend. Feel free to share your thoughts in the comments below or explore other articles on our site about the Golden Age of Hollywood!

Pictures of Olivia de Havilland

4068493 Actress Olivia de Havilland, about 1985 (photo); (add.info.: L

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