Frank Sinatra is one of the most iconic names in the entertainment industry. He rose to fame for his great talent as a singer, and he expanded his legacy after becoming a successful actor. His many successes include films such as From Here to Eternity as well as having a prosperous Las Vegas residency.
Another aspect of Sinatra’s life that has always fascinated the public were his many, many romances. From starting actresses to silver screen legends, Sinatra was well-known for dating a lot of desirable women. Some are only unconfirmed rumors, while others were highly-publicized relationships that grabbed the attention of the world. Let's take a trip down memory lane and see the ladies that went "his way"...
The First of His Many Loves
One of Frank Sinatra’s first loves and perhaps one of the most important ones was his relationship with Nancy Barbato, who adopted his name after their wedding. They were a couple from 1939 to 1951, and they had three children together, Nancy, Frank Jr., and Tina.
Nancy and Frank met each other when Frank was only 19 years old, in New Jersey. By then, Sinatra was only starting to make his way into the entertainment industry. They had Nancy and Frank Jr. before moving to Hollywood, where everything changed, and not for the better.
A Marriage That Crumbled
The Sinatra marriage seemed to be happy, but Hollywood changed things forever. Frank was now incredibly famous, and he could go out with any woman he wanted. News of him cheating on her reached Nancy’s ears, and she was extremely upset about it and confronted Frank.
He promised to do better, and when Nancy was giving birth to their third child, Tina, it seemed like there was a future for them. However, Frank couldn’t help himself and went back to cheating on Nancy, which she couldn’t stand. She decided to end the marriage, although they remained good friends.
A Tumultuous Affair With Ava Gardner
According to numerous reports, it was Frank’s affair with Ava Gardner that ended up being the last straw for Nancy. They were seen having dinner together in 1950, and Frank’s marriage ended the very next year. Allegedly, Frank and Ava had been seeing each other since 1949.
After Frank’s first marriage ended, he proceeded to marry Ava. By then, Ava was one of the best-known actresses in the film industry. Together, they were supposed to be the ultimate power couple. However, Frank’s career was not going well, and this often led to vicious fights between them.
Their Relationship Went South
Both Frank and Ava were extremely willful, and they would often get into highly-publicized feuds. Frank’s frustration at not having a job and steady paycheck clashed with Ava’s undeniable success. According to Ava, Frank even attempted suicide three times while they were married, with two attempts coming very close.
The instability of their marriage led us to believe it was better that no kids came from it. She terminated two pregnancies, and she deeply regretted it. However, she stated that it was for the best. Eventually, they decided to call it quits. Their marriage ended in 1957.
Mia Farrow And Their May-December Romance
Frank Sinatra and Mia Farrow got married in 1966 despite the large age difference. At the time, Frank was 50 years old and Mia was only 21. Before the marriage, Mia had agreed to quit working, but when great roles kept coming her way, she changed her mind.
Frank didn’t like this, and he urged her to stop working. At her refusal, he proposed she work on a project in which he was involved. However, Mia was offered an important part in the film, Rosemary’s Baby. She thought it was a great project, and she couldn’t say no.
May Have Fathered A Child Of Hers
Mia’s decision to do Rosemary’s Baby led the impetuous Frank to call it quits on their relationship only two years after their marriage. Furthermore, he served her the divorce papers while she was on the set of the film. As it tends to happen with Frank’s marriages, they remained good friends.
Such good friends that it was believed Frank could be the father of one of her children, Ronan Farrow, instead of Woody Allen. Rumors about this increased because Nancy Sinatra Sr. and Ronan became very close. She even stated at some point that he was like family.
An Icon Like Marilyn Monroe
Marilyn Monroe is one of the most well-known names around the world. She was an iconic actress, who personified the look of the blonde bombshell. She reinvented herself to become one of the greatest figures in the history of Hollywood. Much like Frank, she had a tumultuous love life.
These kindred spirits got together in 1961, but their relationship was a short-lived one. While reports state that they deeply cared for each other, Marilyn had marriage in mind while Sinatra was not willing to present her with a ring. Their relationship ended amicably after this.
Deciding To Marry Barbara Marx
Barbara Marx was a model and socialite who had been married two times when she and Frank met. In fact, she was married to Zeppo, one of the Marx brothers, when Frank started approaching her. Her relationship with Sinatra effectively ended her 12-year marriage shortly after.
They moved in together, but Sinatra was not convinced about getting married for the fourth time. This led to many arguments and temporary breakups. Barbara was determined to make their relationship more permanent. One day, Frank finally presented her with two precious stones and told her to choose.
A Marriage That Lasted Two Decades
After Barbara selected a huge pear-shaped diamond, preparations for the ceremony began. The idea of a prenup never came up until one hour before they were to be married! Barbara was visited by Frank’s attorney and was told to sign or there would be no marriage. She had a decision to make.
Determined to finish what they had started, Barbara signed the document and the ceremony went through. They were together for 21 years until Frank’s death in 1998. This was the longest and last marriage for the two of them. Barbara died in 2017, one year before Nancy Sinatra Sr.
The Older Woman, Marlene Dietrich
Marlene Dietrich was a force to be reckoned with, and she attracted Sinatra’s attention for her authenticity and willingness to push societal boundaries. Sinatra was 14 years her junior, but this didn’t stop them from pursuing a relationship. Rumor has it they might have gotten involved as early as 1942.
During that time, Frank was married to Nancy. However, this no impediment for him and Marlene to get together. Allegedly, they had an on-and-off relationship for numerous years, and they were often caught on camera. They were both intensely dedicated to their craft, and Marlene was already considered a Hollywood legend.
All The Gossip About Grace Kelly
Many remember Grace Kelly as one of the most talented and beautiful actresses of her generation. She captured the heart of Prince Rainier of Monaco, and she was the star of a real-life fairytale. The Prince was smitten, and they started a relationship that led to their marriage.
However, rumor has it that Grace and Frank might have gotten together in 1956, while they were shooting High Society. This would’ve been quite scandalous considering that Grace had already announced her engagement to Prince Rainier by then. Nothing was ever confirmed, and Grace and Rainier went on to get married.
Another Rumored Romance With Lauren Bacall
Another incredibly famous actress that has been linked to Frank Sinatra is Lauren Bacall. She is remembered for her many performances in the film noir genre, with one of her most acclaimed films being The Big Sleep. She and Frank always said they were good friends.
Despite this, the press often speculated that they were much more than that, and this is a belief that has survived the decades. While nothing was ever confirmed, people thought it was quite likely that they were together during Frank’s marriages, which would have been adultery.
In Comes Judy Garland
Judy Garland started her career as a child actress. The role that catapulted her to fame was the iconic film The Wizard of Oz. However, growing up in Hollywood’s harsh and demanding spotlight was the root of severe mental health issues. Despite this, she had numerous relationships during her search for love.
One of these relationships was with Frank Sinatra. Their forbidden romance would’ve begun in 1949, while Judy was still married to Vincente Minelli and Frank was with Nancy. After Judy’s marriage to Sid Luft ended in 1955, they would’ve gotten together again to resume their relationship.
The Sad Fate That Befell Her
Frank and Judy had a level of fame that was very similar, which leads to the idea that they might have understood each other well. Furthermore, they would both go through bouts of depression, which might have been another subject that brought them even closer.
Despite their similarities, their relationship didn’t last. Judy’s troubled life included pills’ abuse from a very young age. This eventually led to her death in 1969. She had remained friends with Frank, and he was one of the many famous faces who attended her funeral.
Would've Had A Wedding With Juliet Prowse
In 1961, Frank seemed ready to go to the altar once again. He had been dating dancer Juliet Prowse, and he had already asked her to marry him. However, what would become a recurrent issue came up. Frank wanted Juliet to quit work after they got married.
Considering these were other times with different values and traditions, it’s not terribly difficult to understand Frank’s demands. However, Juliet knew she wanted to be a big star and not be at home giving birth to children and cooking meals for her husband. This led them to stop their plans and break up for good.
Lana Turner And Their Scandalous Liaison
Lana Turner was the femme fatale of the ‘40s when rumors of a relationship between her and Frank Sinatra started to surface. This would have been a huge scandal as the two of them were very high-profile artists and this was a much more conservative era.
Lana, who starred in well-known films such as Madame X and The Postman Rings Twice always denied that there was ever a romance. However, it was believed that they had pretended to break things off to avoid the rage of MGM studios. This was not the type of celebrity news the company wanted.
A Romance Interrupted With Angie Dickinson
Angie Dickinson’s fame skyrocketed after the release of the 1959 film, Rio Bravo. However, her relationship with Frank had started before then, in 1954. They had an interrupted romance, which finally ended in 1964. Remarkably, this was one of Frank’s more mellow romances, with little to no drama.
This might have been thanks to Angie’s personality, which proved to be a balancing force for the couple. Frank and Angie starred together in front of the camera during the original Ocean’s 11. After their breakup, Frank managed to maintain his friendship with Angie, even after she got married to fellow actor, Burt Bacharach.
Sinatra's Leading Lady, Donna Reed
Donna Reed was another famous star who got involved with Frank Sinatra. They started their relationship on the set of From Here to Eternity. This film was one of Reed’s greatest successes. For Frank, this was the film that brought him back to Hollywood’s limelight after a few dark years.
Rumor has it that it was Ava Gardner who pulled strings to get Frank this role. Donna and Frank had a short relationship, fueled more by the intense characters they were playing than by a real connection. Donna went on to be one of the main leading ladies of the era.
Gloria Vanderbilt And Their Casual Connection
Frank’s fame led him to become acquainted with some of the richest people in the United States. One of these was heiress Gloria Vanderbilt, who was an author, artist, and designer. They had a laid-back relationship, with on and off encounters throughout the years and a lifelong friendship.
Gloria had shown that she was much more than a spoiled heiress and she became a pioneer in the industry. Evidently, she was a highly intelligent woman, something Frank seemed to value. Their uncomplicated relationship was the subject of much gossip, as people were fascinated by this high-power couple.
The Rumor Mill Ran With Joan Crawford
One of the biggest rumors surrounding Frank’s life was his relationship with Joan Crawford. Joan was one of the biggest Hollywood actresses of her time with successes such as Whatever Happened to Baby Jane. Much like Frank, Joan was well-known for her talent, but also for her unstable romantic life.
Consequently, their deep friendship was the subject of much speculation, and people were convinced there was more going on between them than they admitted. However, neither of them confirmed if they had been involved at any point, although books with their biographies might say the opposite.
Zsa Zsa Gabor In An Unabashed Affair
Zsa Zsa Gabor was one of Hollywood’s most talked-about women. She was extravagant and eccentric, but her beauty and talent led her to great success in the film industry. Zsa Zsa liked to spend her money lavishly, which led her to financial issues. Interestingly, she was married nine times.
Aside from these marriages, she also had numerous affairs with many of Hollywood’s leading men. According to her, one of them was Frank Sinatra, something he never denied. Considering the proclivities for which both of them were known, it’s very likely she was telling the truth.
Jeanne Carmen Was The Opposite Of Ava
Jeanne Carmen is an interesting case when it comes to Hollywood success. She was called the Queen of the B-movies for her many appearances in smaller films with a much more campy style. Despite her films not being considered among the best, she had many fans, and her fame grew considerably.
Jeanne and Frank had a very short relationship, which took place after his breakup with Ava Gardner. With her blonde hair and non-intimidating career, Jeanne was the opposite of Ava, and Frank found solace in her company for a while. Despite this, the relationship didn’t last long.
With Shirley MacLaine, There Was A Spark
Shirley MacLaine starred with Frank Sinatra in the 1958 film, Some Came Running. Many people consider Shirley as one of the most talented actresses of this time, as she was nominated to the Academy Awards six times. While they filmed this movie, sparks flew between Frank and Shirley.
Things didn’t really go much further than the film. Both Shirley and Frank were known for their tendency to get involved with their co-stars. Shirley won an Oscar almost 30 years later for the film Terms of Endearment, and she continues to be active today, showing no signs of going into retirement.
Hedy Lamarr Could've Fallen In Love With Sinatra
Hedy Lamarr and Frank Sinatra’s romantic relationship was never confirmed by either of them. Rumors started flying after they posed together for the cover of Movie Story. Considering that they both had a turbulent romantic life, making the assumption that they could have been together was not entirely baseless.
Hedy, who was both an actress and an inventor, was married six times during her life. Her ease to fall in love made many people think she could’ve fallen for Frank’s charm. Her passion for technology led her to create a radio wave system that could have been the first form of Wi-Fi.
A Short-lived Love Affair With Jill St. John
Jill St. John became known worldwide for her role in the James Bond film, Diamonds are Forever. However, she was much more interested in participating in comedies, such as the 1963 film, Come Blow Your Horn. During the shooting of this movie, she met Frank Sinatra, and they started a short relationship.
They got together again during the filming of Tony Rome. They were only together for the duration of the project, as they weren’t seriously interested in each other. Jill continued to perform in different films, and she later pursued another passion of hers, cooking. She released her cookbook in 1987.
Gina Lollobrigida, Another Romantic Escapade
Gina Lollobrigida is an Italian actress who won the hearts of the United States’ audience during the ‘50s. She had a prolific career for two decades, before deciding it was time to retire. It was during the filming of Never So Few that she and Frank met and started a relationship.
Unlike many of Frank’s romances that started on set, they continued to be together after the cameras stopped rolling. The relationship finally ended one year after they shot the movie. After retiring, Gina decided to become more involved in charity endeavors as well as her love for creating sculptures.
Just A Buzz With Anita Ekberg
Anita Ekberg was a Swedish actress who rose to fame for the film La Dolce Vita, where she stood out from the rest of the cast. She then participated in 4 For Texas, a Western comedy in which she co-starred with Frank Sinatra. Of course, rumors started running rampant about a relationship.
These rumors were fueled by Frank and Anita becoming good friends and making numerous public appearances together. However, the relationship was never confirmed. Eventually, Anita decided to go back to Europe, and she got a property in Italy where she lived until her death in 2015.
The Whispers About Natalie Wood
Natalie Wood rose from child actress to an accomplished leading lady. By the time she shot Kings Go Forth alongside Frank Sinatra, she was 19 years old and a well-known star. According to them, Frank and Natalie were only very good friends, a friendship that lasted for years.
Despite this, news outlets were convinced something more was happening between the couple. Eventually, Natalie married Robert Wagner, whom she would divorce and marry again after a failed marriage to another man in between. Natalie’s death in 1981 is one of Hollywood’s biggest mysteries after she allegedly fell by accident from her husband’s yacht.
Eva Bartok May Have A Kid With Frank
Eva Bartok and Frank Sinatra allegedly had a relationship in 1956. Furthermore, rumor has it that Eva’s only daughter, Deana, was fathered by Frank. No DNA tests were ever made, although the rumor continued for years. At that time, Eva was married to actor Curt Jurgens.
Eva herself stated this claim about Frank being Deana’s father. Despite this, nothing came out of it. Eva, who was married five different times, starred in numerous films both in Europe and in the United States. Furthermore, she released her autobiography in 1959, tilted Worth Living For.
Rumored Romance With Pat Kennedy
According to some sources, Frank would have gotten involved with President John F. Kennedy’s sister, Pat Kennedy. However, this wouldn’t have been born out of any real attraction. Rumor has it that it was a way to get Kennedy’s favor as Frank was allegedly interceding for his friends in the Mob.
These rumors were further fueled by a sworn statement made by a police officer, where he explained the truth had come out after Frank’s phone has been tapped. The timing would have matched with Frank being alienated from Kennedy’s inner circle, of which he had been a part of before.
Jaqueline Bisset Was Another Rumored Love
Jacqueline Bisset and Frank Sinatra starred together in The Detective. Interestingly, it was Frank Sinatra’s wife, Mia Farrow the one who was supposed to star there. However, her filming of Rosemary’s Baby, the movie that ended their marriage, stopped her from doing so. Enter Jacqueline Bisset.
People immediately started speculating, considering that Frank had a history of getting involved with co-stars. However, Jacqueline has denied any relationship. She stated Frank was very good to her and even protective, and that nothing more happened. He would even defend her from the demanding director while they were shooting.
One Of Frank Sinatra's Ultimate Rumored Romances, Elizabeth Taylor
According to the biography, His Way: The Unauthorized Biography of Frank Sinatra, Frank and Elizabeth Taylor would have had a short relationship while she was divorcing Michael Wilding. Much like Frank, Elizabeth was well-known for her many romances and how easily she fell in love.
However, if the rumors are true, this relationship had anything but a happy ending. Allegedly, Elizabeth would’ve gotten pregnant with Frank’s child, and he would have told her it was best for both of them to terminate the pregnancy. While this was never confirmed, speculation ran rampant anyway.