Frank Sinatra is known for being one of the greatest singers of modern times – but he’s also known for his storied love life. The singer and actor had numerous relationships throughout his life, as well as some very high profile affairs and indiscretions.
Sinatra’s first wife was Nancy Barbato, who Frank met in 1934 at the age of 19. The two hit it off and soon entered into a relationship, before getting married in New Jersey in February of 1939.
While in New Jersey, the couple had two children together – Nancy and Frank Jr., born in 1940 and 1944 respectively – and were very happy together. Things began to change, however, when the couple made the fateful decision to move to Hollywood.
Almost immediately after the couple had moved to Hollywood, Frank began having affairs with other women. This was immensely difficult for Nancy, who considered ending their relationship when she first found out.
However, Frank pledged to forego his unfaithful ways, and the two repaired their relationship – having a third child, Christina, in 1948. Unfortunately, Frank was soon to begin cheating again, and Nancy divorced him in 1951. Despite this, the two remained friends for years after, with Frank visiting Nancy regularly until he passed away.
Sinatra’s next marriage, and one of his most intense relationships, would be with fellow actress Ava Gardner. They met on the lot of film studio MGM while Frank was married to Nancy, and it was actually his affair with Gardner that led to their divorce.
After Frank and Nancy’s divorce was finalized, he and Gardner married in 1951. Although the marriage was passionate it was also extremely tempestuous, and the two of them separated in 1953 before divorcing in 1957. Nonetheless, they remained close friends for years afterward.
A woman with presence
Ava Gardner began her career in 1941, and over the years became one of Hollywood’s most well-known and acclaimed actresses. She appeared in numerous films, including ‘The Snows of Kilimanjaro’, ‘Seven Days in May’, and ‘Mogambo’, for which she received an Academy Award nomination for Best Actress.
Throughout her career, Gardner became known as a striking presence on film, and an iconic femme fatale. Gardner was also herself known for having a varied love life, marrying three times, including one marriage to actor Mickey Rooney.
In 1966, Sinatra married his third wife, actress Mia Farrow, when he was 50 and she was 21. Farrow and Sinatra’s marriage seemed to succeed at first – but problems soon started to crop up. Farrow had agreed to stop working at Sinatra’s request, but soon decided she wanted to return to acting, which annoyed Frank.
When she canceled her appearance in Sinatra’s film ‘The Detective’ in favor of appearing in ‘Rosemary’s Baby’, Sinatra served Farrow with divorce papers while she was on the set of ‘Rosemary’s Baby’.
Actress and humanitarian
Farrow rose to fame when she began acting in the 60s TV show ‘Peyton Place’, before moving into film. One of Farrow’s biggest breaks came with the 1968 horror film ‘Rosemary’s Baby’, which saw Farrow catapulted into the limelight.
Over the years, she has acted on stage and screen, winning acclaim as one of the foremost acting talents of her generation. In recent years Farrow has focused increasingly on activism, carrying out charity work across the globe and acting as a UNICEF goodwill ambassador.
Sinatra’s fourth marriage – and the one that went the distance – was to Barbara Marx Sinatra. Frank and Barbara were married on July 11, 1976 – with Barbara even converting to Catholicism for the purpose of marrying Frank.
Despite Sinatra’s reputation for having marriages that didn’t end so well, he and Barbara seemed to buck the trend – with the couple staying together until he passed away in 1998. It seemed that Frank had finally found the person he could spend his life with.
A secure relationship
Barbara herself had been married to someone quite famous before meeting Frank – having spent 14 years married to Zeppo Marx of the legendary Marx Brothers comedic troupe.
Although Barbara was well aware of Frank’s reputation for infidelity, she maintained throughout their marriage that she was never worried that he would leave her for someone else or jeopardize their marriage. After Frank passed away, Barbara gained the enviable privilege of inheriting the rights to his name, likeness, and several of his recordings.
Whispers of an affair
One of Frank’s most famous affairs was one that both parties staunchly denied ever taking part in. During the 40s, it was said that Sinatra engaged in an affair with actress Lana Turner, and that they were quite smitten with each other.
The encounter was hotly speculated, with it even being claimed that Turner and Sinatra pretended to break up just to stop MGM from worrying about the risks of such a high profile affair. However, Turner would later insist that nothing had ever happened between the two.
A big name in the business
It cannot be underestimated just how high profile Turner and Sinatra’s affair would have been. Lana Turner was an icon of the femme fatale archetype – and as one of MGM’s most popular actors was also one of the highest-paid women in film at the time.
Turner appeared in several iconic films, including ‘The Postman Always Rings Twice’, ‘Imitation of Life’, and ‘Madame X’. Several years later, Turner also appeared in the popular TV show ‘Falcon Crest’, considerably boosting the show’s ratings while she was on it.
One of Sinatra’s most widely-speculated friendships was the one he shared with singer and actress Judy Garland. Sinatra and Garland were very good friends, and despite the assumption that they had an extensive affair, the two were only involved briefly.
Their first dalliance came in 1949 during a difficult time for Garland – during which Sinatra took her on a romantic holiday in the Hamptons. The second time came in 1955, when both Sinatra and Garland had separated from their spouses, and sought comfort with one another.
One of the greats
Judy Garland is one of the few Hollywood icons as highly-regarded as a performer as Frank Sinatra. The actress and singer appeared in numerous iconic films, such as ‘A Star is Born’, ‘The Wizard of Oz’, and ‘Meet Me in St. Louis’- all of which she delivered powerhouse performances in.
In addition, her live shows in the later years of her career are regarded as some of the greatest live performances in showbiz history. It’s understandable that two legendary performers would be drawn to each other.
Bacall me maybe
Sinatra was the subject of constant speculation regarding the people he was having affairs with – and actress Lauren Bacall was a particularly frequent presence in these speculations. Sinatra and Bacall were known to be very good friends, but it was often rumored that the two of them had moved their relationship beyond friendship.
On the other hand, it was rumored that Bacall was not interested in Sinatra romantically, but that he was deeply in love with her. Both Sinatra and Bacall denied this, leaving the truth unknown.
A distinctive presence
Lauren Bacall was one of the biggest stars of the golden era of Hollywood – known for portraying wry and intelligent characters, as well as for her striking looks and disposition. She appeared in films such as ‘Dark Passage’, ‘The Shootist’, and perhaps most famously ‘The Big Sleep’ – a masterpiece seen as a defining text in the film noir genre.
Despite her alleged affair with Sinatra, Bacall was faithfully married for years to actor Humphrey Bogart, with whom she starred in several films including ‘The Big Sleep’.
Falling over the first hurdle
Sinatra began a very short but serious relationship in 1961 with Juliet Prowse, a dancer and actress from South Africa. While the relationship progressed steadily at first – with Sinatra and Prowse getting engaged – trouble arose when Frank asked Juliet to give up her career for their marriage.
Prowse simply refused to do so, wanting to focus on building her career and disagreeing with the supposed need for her to quit. As such, the engagement was broken up in 1962 and they parted ways.
Prowse was born in 1936 in British India, before her parents moved to South Africa where she was raised. She studied dance from a young age, wanting to become a famous dancer and actress. She was able to achieve her dream of acting for a time, appearing in films alongside Sinatra and Elvis Presley – and even briefly starring in her own 1965 sitcom ‘Mona McCluskey’.
However, while her acting career never took her to superstardom, she forged an extremely fulfilling and extremely profitable career for herself headlining shows in Vegas.
It makes sense that Hollywood stars with famously tumultuous love lives would attract each other – which is why it might not be much of a surprise to discover that Sinatra had a brief affair with actress Marilyn Monroe.
The two began seeing each other in 1961, not long after Monroe’s marriage to playwright Arthur Miller had ended. The relationship was one marked by great care, but Sinatra knew that it could not last – after Monroe began talking about marriage he broke it off.
An icon among icons
Marilyn Monroe is, without a doubt, one of the greatest icons in film history. Starting her career as a model, Monroe would go on to become one of the most popular (if not the most) and highest-grossing actresses of the day.
Over the years, she put in unforgettable performances in films like ‘Gentlemen Prefer Blondes’, ‘The Seven Year Itch’, and ‘Some Like it Hot’. Even today, Monroe remains one of the most recognizable figures in pop-culture, and continues to inspire artists and actors around the world.
One of Sinatra’s much less turbulent relationships was with actress Angie Dickinson. According to Dickinson, she and Sinatra had pursued an on-off relationship between 1954 and 1964 – one marked by a surprising amount of calm relative to Sinatra’s other relationships.
Dickinson claimed that their relationship was much more mellow and low-intensity than Sinatra’s other dalliances, which was the secret to its success. Even though they would eventually break up, Sinatra and Dickinson remained very good friends for years after their relationship ended.
Since her big break with the 1959 film ‘Rio Bravo’, Angie Dickinson has been a fairly constant presence in film and TV. Over the years she has appeared in numerous films, including the original ‘Ocean’s 11’ (alongside Frank Sinatra), ‘The Art of Love’, and ‘Point Blank’.
In addition, Dickinson played the lead role of Sgt. ‘Pepper’ Anderson in the procedural drama ‘Police Woman’ between 1974 and 1978. Sinatra was far from the only famous singer she had a relationship with – the year after they broke up she married Burt Bacharach.
As far as his romantic relationships go, Frank Sinatra was famous for starting up affairs with his co-stars. One of the actresses that he began a relationship with on-set was Donna Reed, with whom he appeared in the film ‘From Here to Eternity’…
A drama about three American soldiers living in Hawaii in the run-up to the assault on Pearl Harbor. Reed and Sinatra got on very well during filming and had great chemistry with one another – and so they began a short-lived dalliance while filming.
Donna Reed was one of the foremost actresses of her day, appearing in some of the most famous films in Hollywood history. Her two most well-known roles were that of Mary Bailey in Christmas favorite ‘It’s a Wonderful Life’, and Lorene Burke in iconic war film ‘From Here to Eternity’.
Reed was also the star of ‘The Donna Reed Show’ – a sitcom that ran from 1958 to 1966, and was notable for showing a mother figure that was determined and assertive, and for exploring topics like women’s rights.
As one of the most famous men on the planet, it comes as no surprise that Frank Sinatra’s romantic partners were often extremely famous in their own right. One of his most well-known partners was Gloria Vanderbilt, heiress to the Vanderbilt dynasty as well as being an artist and designer.
Although Sinatra and Vanderbilt’s relationship was never truly serious, they were noted to have had several flings over the years, and were very good friends.
Living life to the fullest
Gloria Vanderbilt was obviously well-known as an heiress to the Vanderbilt family fortune – but she also had a prolific career as an artist, author, and fashion designer. Vanderbilt released several fashion lines, and was even one of the first figures in fashion to work on designer jeans.
In addition, Vanderbilt was a keen artist, studying art in New York and even staging two exhibitions. Gloria also enjoyed writing, publishing no fewer than four memoirs, two books on art and decor, and three novels.
A risky choice
Continuing his trend of romancing co-stars, Frank Sinatra was rumored to have pursued an affair with actress Grace Kelly. Sinatra and Kelly starred in the 1956 musical comedy ‘High Society’ – and it was during this time that they were rumored to have become involved.
This would have been a particularly risky move on Sinatra’s part, as Kelly was in a relationship with Prince Rainier of Monaco at the time – had any affair been discovered, the scandal would have been on a level far beyond any other he could have experienced.
Actress to princess
Despite a very short acting career, Grace Kelly’s time on screen turned her into one of the most popular and iconic actresses of the day. Appearing in films such as ‘Mogambo’, ‘High Noon’, and ‘Rear Window’, Kelly became famous for the elegance and quiet power that she brought to performances.
Then, in 1956, Kelly retired from acting after marrying Prince Rainier of Monaco – at which point she became Princess Grace of Monaco. Despite only acting for a short time, she remains an inspiration for many actors.
One of the alleged affairs of Sinatra that has sparked the most debate and discussion is the one he is said to have had with Joan Crawford. As good friends, Sinatra and Crawford were seen together numerous times – and given the tumultuous personal life of both, it was only natural that people would begin to speculate about the nature of their relationship.
Unfortunately, neither of them ever spoke on the matter, so unless somebody discovers a secret diary we’ll never know.
A true star
Over her career, Joan Crawford became one of the most famous actresses in Hollywood history, and remains as such. Appearing in such smash-hit films as ‘Mildred Pierce’, ‘Possessed’, and ‘Whatever Happened to Baby Jane?’, Crawford became one of the most popular actresses in Hollywood, and established herself as an icon of film with a lasting legacy.
Despite the success in her career, Crawford was also notable for a particularly troubled romantic life – marrying no less than four times and remaining single for her last years.
This romantic affair of Sinatra’s is one claimed by his alleged partner rather than him – but there is very little reason to doubt the truth of it. Actress Zsa Zsa Gabor once claimed that she had engaged in numerous flings with Sinatra over the years – a fact he neither confirmed nor denied.
However, given the common knowledge of Gabor’s many affairs with men in Hollywood – and Sinatra’s love of romance – it is very likely that she was telling the truth when making this claim.
There are not a lot of famous figures that are as unique as Zsa Zsa Gabor – a notable individual even in the world of Hollywood. Coming to the United States from Hungary in 1941, Gabor soon became a popular actress as a result of her presence and personality.
In addition, Gabor became famous for her very individual style – adopting a lush, lavish lifestyle, as well as an extravagant and opulent mode of dress. She was also a famous romantic, marrying no less than nine times.
Frank Sinatra was as well known for the failures of his relationships as he was for their successes, with one often leading to the other. In this case, his separation from Ava Gardner led to a brief relationship with Jeanne Carmen, a model and actress at the time.
Sinatra was devastated after his split from Gardner, and turned to Carmen for comfort after they separated. Although the relationship was only short-lived and never particularly serious, Carmen looked upon the time fondly.
Jeanne Carmen never made it particularly big in the movie industry – but did develop a sort of fame as a frequent performer in smaller, less high-profile films, eventually being named ‘Queen of the B-Movies’.
Carmen appeared in well-known B-movies such as ‘The Monster of Piedras Blancas’, ‘Untamed Youth’, and ‘The Devil’s Hand’ – eventually becoming something of a cult icon due to the camp nature of the films she appeared in, and her unique, glamorous appearance. As such, her legacy managed to grow outside of the small films she appeared in.
A kindred spirit
Frank Sinatra was far from the only person who had a tendency to end up in flings with his co-stars – as he would find out when he met actress and singer Shirley MacLaine. The two met on the set of 1958’s ‘Some Came Running’, a film about a veteran who searches for fulfillment after returning to his hometown.
Sinatra and MacLaine would begin their affair soon after filming began, although it was short-lived. MacLaine was a kindred spirit with Sinatra, admitting that she too often developed feelings for her co-stars.
An illustrious figure
Shirley MacLaine is one of the most well-recognized and highly-acclaimed actresses of her generation, netting no less than six Academy Award nominations throughout her illustrious career – finally winning for the 1983 film ‘Terms of Endearment’.
As well as a successful career in acting, MacLaine has also moved into other fields, directing the 1975 documentary ‘The Other Half of the Sky: A China Memoir’ – which received an Oscar nomination for Best Documentary. In addition, she has written over a dozen books.
Rumors and speculation
One of the most persistent and unverified rumors around Sinatra’s romantic life was that he had been involved with the actress Hedy Lamarr. Sinatra met Lamarr when they appeared together on the cover of the magazine ‘Movie Story’.
Since then it has been constantly speculated that they were involved with one another – rumors helped along by the fact that Lamarr was one of the few people who could trump Sinatra as far as romantic trouble was concerned – marrying and divorcing no less than six times.
A great mind
Hedy Lamarr was truly one of the most unique and ahead of her time figures in Hollywood – being an actress as well as a prolific inventor. As an actress, she was lauded for her captivating on-screen presence, appearing in films like ‘Lady of the Tropics’, ‘Samson and Delilah’, and ‘The Female Animal’.
However, off-screen, Lamarr had a deep passion for inventing, constantly tinkering and developing different gadgets. In fact, Lamarr and composer George Antheil even worked together on a radio guidance system that was a precursor to current wi-fi technology.
Frank St. Sinatra
In the history of film, Bond girls have become a sort of shorthand for smart, beautiful and independent women. If there is anyone you could expect to be with a Bond girl, it’s Frank Sinatra. Sinatra met Jill St. John – who appeared as Tiffany Case in ‘Diamonds are Forever’ – while they were working together on ‘Come Blow Your Horn’ in 1963.
Sinatra and St. John began a brief fling, which ended when filming did – and resumed when they worked together again on ‘Tony Rome’ in 1967.
Jill St. John’s most famous role was that of Tiffany Case in the James Bond film ‘Diamonds are Forever’ – but it was far from the sort of work she wanted to do. Although she acted dramatically several times, St. John’s greatest passion and talent lay with comedy.
As such, she was happiest when working on comedic films like ‘Come Blow Your Horn’, ‘Honeymoon Hotel’, and ‘Eight on the Lam’. She was also keenly interested in cookery, publishing her own cookbook – ‘The Jill St. John Cookbook’ – in 1987.
One of Sinatra’s most iconic romantic partners was actress Marlene Dietrich, with whom Sinatra was said to have had several flings, starting in 1942. Despite being 14 years older, Dietrich was more than a match for Sinatra…
For every romantic conquest he could name she could name two – and the two were known to get along with each other very well. What’s more, this affair is far from mere speculation, with Dietrich herself claiming that she and Sinatra had been involved.
A titan of the 20th century, Marlene Dietrich was one of the most famous and revered actresses of her – or any – generation. Her breakthrough role was in the 1930 German film ‘The Blue Angel’ – after which she soon became famous for her dynamic and intense presence, as well as her striking appearance – breaking several gender norms in the way she dressed.
After conquering the screen, Dietrich became a legendary touring performer – and to this day inspires numerous artists, performers, and actors.
A ‘serious’ friendship
Throughout the ’50s and ’60s, Natalie Wood was one of the most famous actresses in Hollywood known for her performances in movies like Rebel Without a Cause and West Side Story. Wood first met Sinatra on the set of the 1958 film Kings Go Forth, where they played an on-screen couple – she was just 15 years old at the time while Sinatra was 43.
Despite their age difference, the pair became ‘serious’ friends for many years to come – although there were always rumors that they were something more than just good pals.
Natalie Wood continued to star in films and TV shows until the ’70s, when she took a brief hiatus from the screen to take care of her two children. She was married to actor Robert Wagner – who she married, divorced, and remarried again after divorcing her second husband, producer Richard Gregson.
Tragically, Wood passed away in 1981 at the young age of 43. She had drowned while taking a trip to Catalina Island on her husband’s yacht. Still to this day her death remains one of the most mysterious in Hollywood history, with many unknown circumstances – such as how she fell in the water in the first place.
Italian actress Gina Lollobrigida won over the hearts of many famous men back in the day, but one of the most high-profile she was rumored to have had a fling with was Sinatra. The two met while working on the the 1959 drama action film Never So Few, where they portrayed on-screen lovers.
However, it was rumored that the two co-stars took their undeniable chemistry off the screen as well, continuing for about a year following filming.
Gina Lollobrigida was certainly an icon of the ’50s and ’60s, starring in films such as The Hunchback of Notre Dame and Come September. However, she continued to work all the way up until 1997, where she starred in the 1997 romantic-comedy XXL. The actress retired after that and received a star at the Hollywood Walk of Fame in 2018.
She has also been focusing on charity, selling her jewelry collection in 2013 and donating nearly $5 million to benefit stem cell therapy.
Another co-star that Sinatra reportedly had an affair with was Anita Ekberg, who played opposite him in the 1963 Western comedy 4 for Texas – along with Dean Martin and Ursula Andress. Sinatra apparently fell for the blonde Swedish actress – who earned fame in 1960 thanks to her fiery performance in the Federico Fellini film, La Dolce Vita.
Although nothing was ever confirmed between the famous pair, they would often show up together to parties looking awfully comfortable with one another.
Life in Italy
While Ekberg may always be known for her role as Sylvia in La Dolce Vita, she did go on to star in several more films after that, the majority in Italy, which she made her permanent residence in 1964. She worked up until 2002, with her last role on an Italian drama series called Beauty Centre.
She continued to live in Rome until her death in 2015, sadly passing away at the age of 83 following complications from a series of illnesses.