Frank Sinatra was one of the most popular entertainers of the 20th century. The singer and actor won an Oscar and spent decades in the spotlight. The women he dated had a significant impact on his life. Frank’s first wife was Nancy Barbato, his childhood sweetheart. They met long before his career took off. 

They had three children: Nancy Sandra Sinatra (born 8 June 1940), Francis Wayne Sinatra (born 10 January 1944), and Tina Sinatra (born 20 June 1948). Frank and Nancy split up four years after Tina’s birth. Frank and Nancy were deeply in love, but their marriage didn’t last. Frank left Nancy for another woman, which was very sad. They officially divorced in 1951. After they split up, Nancy got custody of the children and raised them. However, the children said Frank was still a big part of their lives. Nancy never remarried. She remained single until she passed away at 101.

While he was married to Nancy, Frank saw the well-known Hollywood star Ava Gardner. The two had a rocky 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 the actress Lana Turner. Ava revealed that she had two abortions while she was married to Frank. Judy Garland was another actress with whom Frank was involved.

They kept their relationship hidden for a while but were seen together in a restaurant in 1950. Frank and Ava loved each other intensely but fought a lot. In 1953, Ava started a relationship with the Spanish bullfighter Luis Miguel. Sinatra tried to win her back, but they divorced in 1957. Gardner never remarried, and in 1982, she told London’s Daily Express that she would have happily traded her career for one lasting marriage. Despite Sinatra’s attempts to win her back, the two never returned together.

Frank had many controversial partners during his lifetime, and Lauren Bacall is at the top of the list. 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 it a secret. However, the news of their engagement was leaked, and Sinatra was unhappy about the media attention. He contacted Bacall and said they should keep their distance from each other, and this was the end of their relationship.

Frank Sinatra and Marilyn Monroe were two of the most famous couples in Hollywood.

Monroe and Sinatra were two of the most famous people in the world at the time, and they had a secret relationship for many years. This eventually led to Frank proposing to her.

However, she turned him down when he asked her to marry him.

She reportedly rejected him because she was feeling very sad and had suicidal thoughts. 

A year after Marilyn said no, Frank proposed to the India-born South African actress and dancer Juliet Prowse. They got engaged two years later but only lasted six weeks before calling it off. People were shocked when he started dating Mia Farrow, 21 years younger than him. 

When he and Farrow split, he was in his fifties, and he dated Irene Tsu soon after. She was 29 years younger, and their first date was when his marriage to Farrow collapsed.

Much to her father’s relief, the relationship ended after only two years.

At 58, Ol’ Blue Eyes was still a catch. He charmed ladies and swept them off their feet. He won over Barbara Marx, and she said yes to walking down the aisle with him. Barbara eventually divorced Marx in 1973 and married Frank on 11 July 1976, after he proposed with a 20.6-carat diamond ring. Frank’s three children followed different paths. The eldest, Nancy Junior, became a singer like their father, while Frank Junior lived off his reputation. Christina tried various things until she decided to record her dad’s memories in her book My Father’s Daughter, which was released in 2015, the 100th anniversary of Frank Sinatra’s birth. Tina shared her unique insight into her father’s life through her writing and his thoughts.

Frank Sinatra loved often and loved hard most of the time. His spouses played an essential role in his life, each uniquely shaping his life and career. Each woman brought a unique challenge, influence, and story: from his first wife, who was always loyal, to his last wife, who was always supportive. Even the brief relationships between marriages were an essential part of the legend that he was and will always be.

Each woman left an indelible mark on Frank Sinatra and his legacy, from Judy Garland to Marilyn Monroe.