Frank Sinatra remains one of remarkable in the history of entertainment, thanks to his impressive voice and charismatic personality! In addition to singing and performing, Frank also liked hooking up with the ladies during his time. Frank marry four different women throughout his lifetime and hooked up with many, many more! Join Facts Verse as we take a look at every woman Frank Sinatra dated or hooked up with.
Although Vikki LaMotta might not have been the first female Frank Sinatra was ever with during his lifetime, their fling stands as Frank’s first publicly documented romance. Vikki, known as the second wife of boxer Jake LaMotta, is the inspiration for Martin Scorsese’s Raging Bull. However, she later revealed that she had a fling with Frank Sinatra beforehand.
Actress Nancy Berg claims that she hooked up with Frank Sinatra very early in both of their careers.
Zsa Zsa Gabor
Zsa Zsa Gabor, another celebrity involves in Frank Sinatra dated romantically for a time, with them reportedly getting together in 1931.
Nancy Barbato became Frank Sinatra’s first wife in 1939, and the two stayed together until 1951. Frank and Nancy have three children together, one of those children respects Nancy Sinatra. Sadly, the two couldn’t make their marriage work and ended up divorcing. Frank encounters numerous affairs after he married Nancy, and his infidelities are because of his alcoholism.
One of Frank’s women is Marlene Dietrich during his married life. Frank and Marlene got together in 1944, though Frank’s fling with the actress didn’t last very long.
After hooking up with Marlene Dietrich during his marriage to Nancy Barbato, Frank started another extramarital affair with actress Lana Turner. Lana was an even bigger deal than Marlene was back in the day, and young Frank likely considered himself pretty lucky when he dated her from 1946 to 1947. At the height of Lana’s success, she was one of the highest-paid women in the entire world!
After Lana Turner, Frank Sinatra moved on to Joan Crawford. Frank was still technically with Nancy when he and Joan hooked up in 1947. Joan was a very popular actress at the time, having signed her first contract with MGM several decades prior, in 1925.
Frank Sinatra and Judy Garland were lifelong friends, but they were also lovers on a couple of occasions. Frank and Judy have two separate flings throughout their lifetime, the first is when Frank married Nancy and the second is when he married his second wife Ava Gardner, who will be coming up shortly in this video! Although Frank and Judy never made their relationship serious, the two maintained a friendship over the years after their second fling, and Frank reportedly helped pay for Judy’s funeral.
After divorcing first wife Nancy Barbato in 1951, Frank Sinatra quickly moved on to second wife, Ava Gardner! Frank and Nancy’s marriage had been turbulent, and Frank and Ava’s was arguably even worse. Both of the celebrities relied on alcohol during that time, and Frank kept up his habit of being unfaithful over the course of his second marriage.
In 1954, while married to Ava Gardner, Frank Sinatra have an affair with actress Donna Reed. Donna is one of four celebrities that romantically involved with Frank that year.
Another of the four celebrity figures that Frank Sinatra was reported to have started up an affair with in 1954 is Grace Kelly. Of course, Grace Kelly was a famous actress before deciding to abandon the entertainment industry to become the official Princess of Monaco after marrying it’s prince.
The third celebrity that Frank Sinatra reportedly had a fling with in 1954 is Gloria Vanderbilt. Gloria was a celebrity for a variety of reasons, not the least of which being the fact that she was a member of the prestigious Vanderbilt family of socialites. As an heiress, Gloria proved to be one of the most respected figures that Frank Sinatra hooked up with. That is, besides the aforementioned Princess of Monaco!
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After working his way through Donna Reed, Grace Kelly, and Gloria Vanderbilt, Frank Sinatra still didn’t feel as if he had cheated on second wife Ava Gardner enough! Thankfully, Ava was likely too busy having drunken affairs of her own to notice her husband’s infidelity. Angie Dickinson is the final of the four celebrities that Frank Sinatra is known to have had an affair with during 1954. However, Frank’s relationship with Angie lasted past the year. Frank and Angie maintained a casual relationship for an entire decade after getting together in 1954, with it reportedly lasting until 1964.
After the affair-ridden year that was 1954, Frank was only known to have had one affair in 1955. That affair was a fling that Frank shared with a French actress and dancer by the name of Leslie Caron.
Frank Sinatra had two affairs during 1956, one of them being with Hungarian-British actress Eva Bartok.
The other celebrity figure that Frank Sinatra reportedly had an affair with in 1956 is actress Joan Blackman, who remains best known for her roles in a few Elvis features.
In 1957, the same year that he divorced Ava Gardner, Frank Sinatra reportedly started up a casual relationship with model Jeanne Carmen that lasted until 1960.
Lauren Bacall was another celebrity figure that Frank Sinatra reportedly struck up a casual relationship with in 1957, with their relationship reportedly lasting until 1958.
Another celebrity figure that Frank Sinatra reportedly had a fling with in 1957 is actress Venetia Stevenson.
Judith Exner was a woman that Frank Sinatra was romantically involved with in 1958. Nowadays, Judith remains better known for the affair that she had with president John F. Kennedy before his untimely death.
From 1958 to 1959, Frank Sinatra was said to have been dating Italian actress Gina Lollobrigida. When the two were dating, Gina was a renowned sex symbol.
Although Frank Sinatra and Juliet Prowse never married, they were romantically involved for well over a decade, from 1959 to 1975. Although they weren’t technically together the whole time, they dated sporadically over the period.
Frank Sinatra couldn’t have been a respectable womanizer during Hollywood’s Golden Age without hooking up with Marilyn Monroe. Frank was one of the more notable figures that Marilyn hooked up with over her short life, and she’s also another of Frank’s former lovers that was romantically involved with John F. Kennedy. Frank and Marilyn’s romance lasted for a few years, from 1959 to 1961.
Around the same time that Frank was involved with Marilyn Monroe, he was also dating actress Kipp Hamilton. Frank and Kipp dated from 1959 to 1960.
Frank Sinatra dated jazz singer Keely Smith in 1961.
Jill St. John
Frank Sinatra hooked up with future Bond girl Jill St. John in 1963. She would later become most widely known for her performance in 1971’s Diamonds Are Forever.
Mia Farrow was Frank Sinatra’s third wife, and Frank considered the actress to be the love of his life up until his death. This revelation came in spite of the fact that the two were only married from 1966 to 1968. They maintained a friendship after their marriage ended, and many believe that Mia’s son Ronan was actually fathered by Frank.
One of the reasons that Frank Sinatra’s marriage to Mia Farrow didn’t work out was because Frank couldn’t let go of his unfaithful habits. Frank reportedly had an affair with actress Natalie Wood in 1966, while married to Mia.
After divorcing Mia Farrow, Frank Sinatra was involved with Chinese actress Irene Tsu from 1968 to 1969.
Frank Sinatra hooked up with future Dallas actress Victoria Principal for a short period in 1972.
In 1972, Frank Sinatra also dated actress Hope Lange.
Frank Sinatra reportedly had a short affair with actress Elizabeth Taylor sometime in the early 1970s.
Judith Exner and Marilyn Monroe weren’t the only lovers that Frank Sinatra reportedly shared with John F. Kennedy. More than a decade after the former president’s death in 1963, Frank allegedly hooked up with former first lady Jacqueline Kennedy in 1975.
Finally, Frank Sinatra married fourth and final wife Barbara in 1976, and they remained together until the legendary crooner’s death in 1998. Although Frank went to his deathbed claiming that actress Mia Farrow was the true love of his life, his two-decade-long marriage to Barbara suggests otherwise. Frank’s marriage to Barbara was the most successful marriage that the entertainer experienced over the course of his lifetime by far, and a big part of that was probably the fact that he had gotten many, many extramarital affairs out of his system in the years beforehand!
Although Frank Sinatra hooked up with some of the most beautiful women of Hollywood’s Golden Age, he went to his deathbed claiming that actress Mia Farrow was the true love of his life. Now it’s time to hear from you: did you know that Frank Sinatra and former president John F. Kennedy shared at least three lovers, or did you think that politicians and entertainers never ran in the same circles? As always, like this video to show your support, and subscribe and hit the notification bell if you’d like to be among the first to know when more Facts Verse videos are on their way!