From Marilyn Monroe to Grace Kelly, Here Are All of the Ladies in Frank Sinatra’s Life

Frank’s first walk down the aisle was with Nancy Barbato, his childhood sweetheart. His relationship with Nancy started well before his career took off. They met in Long Branch, New Jersey, when Nancy was 17, and Frank was 19. Nancy and Frank’s families spent their summers in the seaside town, and the lovebirds met there in 1934. Their meet-cute was something straight out of the movies. Frank was playing love songs when he first saw her on the porch giving herself a manicure. They fell in love, began dating, and got married in 1939, during the height of the Great Depression.

Frank and Nancy had a great marriage before the singer found fame. Nancy was a doting wife, working as a secretary to support Frank as he tried to get his big break. Long before Frank had the money for designers and custom-made outfits, Nancy sewed his outfits and that of their children. She made sure her husband and children were well-fed, making them classic Italian food from time to time. Although they weren’t financially buoyant, they were happy. However, their happiness started to dwindle as Frank started to get famous.

Frank found success as a solo artist in 1943 after signing with Columbia Records. As his career really kicked off, Frank had a new persona, and as expected, his fashion sense changed. Nancy did her best to keep up with his new persona. She changed her wardrobe and got her teeth fixed while trying to change her image to suit his. Unfortunately, her efforts were mostly futile. She was still referred to as “Big Nancy” despite the changes she made. She tried to fit into Frank’s new life, but she just couldn’t. ​While he was still married to Nancy, Frank started dating other women who fit into his new life. 

After Frank and Nancy split, Nancy got custody of the children, and she assumed the primary role of raising them. However, the children have said that Frank remained a large part of their lives. All three children pursued careers in the entertainment industry, singing and acting like their father. Although Nancy described her marriage as unhappy, she remained close to Frank after the divorce. She made sure he was cared for and well-fed, even going as far as passing on recipes of his favorite dishes to his staff. Frank would visit Nancy and his kids, make late-night phone calls with them, and have family dinners.

One of the women Frank saw while he was married to Nancy was the well-known Hollywood star Ava Gardner. The affair lasted a few years as Nancy did not want to grant Frank a divorce. She eventually gave in, and the divorce was finalized on October 29, 1951. A week later, Frank got married to Ava Gardner. The two had a tumultuous relationship as they both had affairs while they were married to each other. While he was married to Ava, Frank had a very public affair with actress Lana Turner. He was so enamored by her that he left his wife for her. Unfortunately for him, it didn’t work out and he returned to his wife.

Judy Garland was another actress with whom Frank was involved. They met in 1949 when Judy was recovering from a nervous breakdown. The two went on a romantic rendezvous in the Hamptons while Judy was still married to director Vicente Minnelli. After their romantic rendezvous, their affair stopped but resumed in 1955 when Judy was separated from her third husband, Sid Luft. The two legendary singers exchanged letters while they were together. One of the letters Garland wrote after their secret rendezvous in the Hamptons was found.

Sinatra was romantically involved with Lana Turner and Judy Garland, but it was only Ava Gardner that he committed to and married. After meeting at a club in 1943, Sinatra and Gardner saw each other occasionally but reconnected in the late 1940s while Frank was still officially married to Nancy. At that point, Gardner’s career was taking off. MGM studio executive Louis B. Mayer warned her about getting involved with Sinatra, a married man who was also several years her senior. They ignored all warnings and kept seeing each other. The couple kept their love hidden for a while until they were papped in a restaurant in 1950.

Frank and Ava’s relationship was controversial. For starters, they were both married to other people when they first got together. Frank was married to Nancy, while Ava’s husband was fellow actor Mickey Rooney. However, Sinatra wasn’t fazed. He was determined that they would be together before even meeting her. He saw her photo and said, “I’m going to marry that woman.” Ava was no stranger to scandalous love affairs either. She reportedly had a reputation for cheating on her spouses.

Frank married Ava, who was the woman of his dreams at that point. The passion was there, and the romance was too, so walking down the aisle was the logical thing for them to do. However, they both had a reputation for cheating on their partners, and this almost caused a hitch in their marriage plans. The night before they got married, a prostitute disclosed to the soon-to-be wife that she and Frank had been having an affair. Gardner went ahead with the wedding, but the jealousy the revelation sparked turned into arguments that even the general public wasn’t spared from.

Frank and Ava loved hard, but they fought harder. Their fights were legendary (Frank reportedly threw a douchebag filled with water at her), and their make-ups were loud. But the drunken fights and the affairs weren’t the only problems in their marriage. Gardner was at the peak of her career and was earning more than Sinatra. Sinatra, on the other hand, was struggling financially and had to rely on his wife to support him. It’s no surprise that Ava aborted two pregnancies because she felt she could not rely on her husband for financial support and general stability.

Despite Sinatra’s attempts to win Gardner back, the two never got back together. Many still believe that, for Frank Sinatra, Ava Gardner was the one who got away. After his failed attempts to get Gardner back, Sinatra moved on with Angie Dickinson, another Hollywood star (Frank certainly had a type). They met when Dickinson guest-starred on The Colgate Comedy Hour and saw Sinatra and Jimmy Durante perform. They became friends after that but were not romantically involved.

Frank had many controversial partners during his lifetime, and Lauren Bacall is at the top of the list. Bacall was a Hollywood actress who was married to Humphrey Bogart, a close friend of Sinatra. The main reason the public frowned at their relationship was because it started while Bogart was down with an illness that eventually killed him. Bacall found solace in Sinatra, and the two reportedly started their affair while Bogart was still alive. After his death, they got engaged, but Sinatra asked her to keep the engagement quiet.

Frank Sinatra and Marilyn Monroe were one of the most iconic pairs in Hollywood during their time. They met in 1953 when their studios considered pairing them in the remake of a Betty Grable musical, Pink Tights. At the time, Sinatra had just won an Oscar for From Here to Eternity, and Monroe was a star after her roles in Gentlemen Prefer Blondes and Niagara. Sinatra tried to keep the relationship a secret to avoid upsetting Monroe’s ex-husband, Joe DiMaggio, who was also his friend.

The couple started out as friends and eventually evolved into a casual fling. They were so close that they even lived together for a time. After a while, their casual fling became a passionate, romantic affair. The couple were reportedly so enamored by each other and spent a lot of nights together. Marilyn used to say, “If I have any problem, there’s only one person I know can help: Frankie.” 

Unsurprisingly, everyone was shocked when Sinatra announced his engagement to Juliet Prowse. As far as everyone knew, Frank and Marilyn were very close and were very well on their way to marriage. The couple’s romance came to an end, but they remained good friends. He noticed she wasn’t doing well and saw how much more depressed she had become. As a good friend, he tried to help her, doing everything he could to bring her out of her depressed state, but sadly, she passed away.

A year after Marilyn turned down his proposal, Frank proposed to the India-born South African actress and dancer Juliet Prowse. The two first met on the set of the 1960 film Can-Can. And two years later, they got engaged. Frank’s friends were skeptical of his relationship with Prowse, as they strongly believed that it was a rebound from Marilyn. Their engagement only lasted for only six weeks before they called it off.

If you’ve not already guessed, Frank Sinatra didn’t always consider public opinion when choosing his love interests. To be fair, it wasn’t really anyone else’s business anyway. After he ended it with Prowse, people were shocked at the new actress he got together with. Sinatra was 50 years old when he walked down the aisle with 21-year-old Mia Farrow. She was less than half his age and younger than Frank’s first daughter, Nancy.

Frank and Mia were in love and didn’t care what the rest of the world thought about their relationship. The large age difference between the two meant nothing to them, but it was the main thing the public criticized. So while Mia was calling him “Charlie Brown” and Frank was calling her “Angel Face,” the rest of the world called the couple less kind words. A year before they got married, Mia sheared her long, blond tresses, shocking everyone. Although she claimed she did that on impulse, others claimed she did it in retribution for having to stay home the night Sinatra’s family threw him a 50th birthday gala.

The public got a glimpse of Frank’s controlling behavior when he was with Prowse. She ended her relationship with him because he wanted her to give up her career. Frank’s controlling streak resurfaced when he married Mia and tried to make her choose between him and her job. It was revealed that one of the reasons they split was because they disagreed about her career. Frank saw himself as a “good provider” and couldn’t understand why she would want to work. ​In 1968, Farrow was offered the lead role in Rosemary’s Baby, and she took it.

Although their marriage ended bitterly and prematurely, Frank and Mia remained on good terms. Mia, still a young, pretty woman in Hollywood, quickly moved on to relationships with other Hollywood stars. She married Andy Previn, a musician, divorced him, and ended up with director Woody Allen. They dated for 12 years and had three children together: Dylan and Moses, who were adopted, and Satchel, who was biological and later changed his name to Ronan. In 1992, Farrow discovered that her partner was having an affair with Soon-Yi Previn, her adopted daughter.

Sinatra’s relationship with the much younger Farrow elicited various reactions from people, from shock to disdain to consternation. However, Frank didn’t allow the controversy to deter him from pursuing younger women after his divorce. He was in his fifties when he and Farrow split, and he dated Irene Tsu soon after. Tsu and Sinatra met in Miami, Florida, while filming Tony Rome and “Chevron Island” commercials, respectively. She was 29 years younger, and they had their first date amidst the collapse of his marriage to Mia.

Tsu first met Sinatra at a lunch she was invited to by her manager. “I remember this long table with maybe eight or nine people,” she recalled. “And then you heard the voice. You didn’t even have to look up to know it was Sinatra’s. The voice just commanded the room. And I didn’t want to look for him. I felt like I wasn’t allowed, and I didn’t want him to catch me staring!” Tsu seemed to have had a crush on Sinatra, and it was not a surprise she agreed to follow him out to the desert when he asked out of the blue.

Tsu and Sinatra had a great time on their first date, with Tsu describing it as “a magical weekend.” They got back, and Tsu followed Frank home, staying in Mia’s old room. She felt right at home, even going as far as changing the room from pink to buttercup yellow. She was swept off her feet, but her father was “furious” about her relationship with Sinatra. For Tsu, the Chairman of the Board was “hard to resist…He had the most incredible blue eyes, and if he looked at you, forget it.”

Sinatra’s affair with Grace Kelly was arguably one of his most scandalous affairs. They first met on the set of the 1952 film Mogambo. They later worked together on the set of the 1956 musical film High Society. Grace Kelly was a Hollywood star, like most women in his life. However, she wasn’t just any Hollywood star. She was also a princess after marrying Prince Rainier of Monaco, who was good friends with Sinatra. ​Kelly was idolized as the cool, graceful, and classy paragon of female elegance. 

Frank’s career kick-started in his twenties, but it wasn’t until he was in his fifties that he really started to peak. His talent as a singer and actor, coupled with the fact that he was a member of the Rat Pack, probably helped him get on nicely with the ladies. At 58, Ol’ Blue Eyes had no trouble with charming ladies and sweeping them off their feet. He managed to win over Barbara Marx, and she said yes to walking down the aisle with him.

Barbara’s friends were shocked when she ignored Frank’s invitation. One of the girls with her said, “Do you know who that was? That was Frank Sinatra.” To which she replied, “I don’t care; I don’t want to deal with drunks.” She was married to her second husband, Zeppo Marx, one of the legendary Zeppo brothers. At that moment, she didn’t care who Frank Sinatra was. However, like most of the women in Frank’s life, Barbara couldn’t resist his charm.

Sinatra had been married three times already, but the fourth time was the charm, as the marriage was his last and longest one. Lady Blue Eyes, as Barbara referred to herself in her memoirs, divorced Zeppo Marx and married Frank 3 years later. They were married for 22 years until Frank died in 1998 at the age of 82. This was Frank’s longest marriage, with his marriage to Nancy being the second longest. Frank’s marriage to Barbara was also the only one that didn’t end in a divorce. ​They held the wedding at Sunnylands, a desert estate just down the street from Sinatra’s home. 

The Chairman of the Board had many romantic relationships with different women over the years. However, the two women he loved the most and prioritized were his daughters, Nancy and Tina. Frank wasn’t a saint, but his eldest daughter, Nancy, has always had good things to say about him. On several occasions, she has mentioned how good a father he was to them. At least there was consistency when it came to his girls.

After her father’s death, Nancy has been more vocal about the other qualities of Frank Sinatra that people don’t often see. He was known as a legendary singer who had one scandalous affair after another. According to Nancy, many people didn’t know that he was also incredibly compassionate. He once helped a little girl he never met with all her medical bills after reading about her in a newspaper.

Although Sinatra found love with Barbara, no love was lost between her and his children. Sinatra’s children claimed that his wife refused to acknowledge their presence in his life. Consequently, both parties didn’t get along. When Sinatra was on his dying bed, Barbara didn’t inform his children in time, and they couldn’t say goodbye to their dad. As expected, his children were upset. “His road manager was told, his PR was told, and my step-brother was told, but none of his children.

Frank loved a lot of women, and it was very easy to recognize that he had a type. He was fussy about the type of women who became close to him and wasn’t shy about it. He judged a lady by her hands, observing how well-kept they were. To him, they were a reflection of how well she took care of herself. He liked his ladies classy, funny, and with little make-up.

On his dates, Sinatra always ensured he brought class with him. He kept things simple but classy. The singer had a lot of money and resources at his disposal but rarely flashed it. Where others would choose to hire a fancy limo to impress their dates, Sinatra would prefer to drive his dates. He avoided going to glitzy parties, mainly because he was a terrible dancer and didn’t want to embarrass himself.

Frank’s three children followed different paths. The eldest, Nancy Junior, became a singer like their father, while Frank Junior lived off Sinatra’s reputation. Christina dabbled in different things until she decided to record her dad’s memories in her memoir, My Father’s Daughter. Released in 2015, the 100th Anniversary of the birth of Frank Sinatra, Tina shared the unique insight she had into her father’s life through her writing and his thoughts.

Tina’s memoir is riddled with revelations and peppered with fond memories, reflections, and regrets. She received criticism from some people because of the negative insights into her memories and the stories of the many women in Frank’s life. Even Tina’s mother, Nancy, tried to stop her daughter from releasing the book. However, Tina didn’t let the negative comments weigh her down. She was committed to telling her story and spent eight years of her life doing so.

Frank Sinatra loved often and loved hard most times. His spouses played pivotal roles in his life, each one uniquely shaping his life and career. Each woman brought a unique challenge, influence, and story from his very first wife and her steadfast loyalty to his last wife and her nurturing support. Even the flings he had between marriages were integral parts of the legend that he was and will always be.