30 Of Frank Sinatra’s Lovers You (Probably) Forgot About


He is one of the most popular and influential musical artists of the 20th century. His music touched the heart of his fans worldwide. Because of that, many people consider his music as timeless. Due to his 150 million records sold worldwide, he is one of the best-selling music artists of all time. That man is Frank Sinatra, a singer born in 1915 in Hoboken, New Jersey.

Because of his music, many fans all around the globe fell in love with him. These devoted fans were known to write Sinatra’s song titles on their clothing, bribe hotel maids for an opportunity to touch his bed, and accosted him in the form of stealing the clothing he was wearing, most commonly his bow tie.


People outside of show business weren’t the only ones falling in love with Sinatra. Many actresses and singers loved him as well. That is why he had so many relationships throughout his life. He was married four times and had at least six confirmed love affairs, not counting those unconfirmed ones. Here is the long list of them, and let us know which ones you think are real or not!

1. Grace Kelly


She was an American actress who became Princess of Monaco after marrying Prince Rainier III. Before that, she had a relationship with other actors. It was rumored that she had a romantic relationship with Frank Sinatra off-screen when they worked together in High Society.

2. Judy Garland


Judy Garland was romantically involved with Sinatra on two occasions. The first was in 1949, when Garland was recovering from a nervous breakdown and the two went on a romantic rendezvous in the Hamptons. At the time, she was still married to director Vincente Minnelli. The second was during one of Garland’s many separations from her third husband, Sid Luft, in 1955.


3. Joan Crawford


Joan Crawford and Frank Sinatra have few things in common. They were both married four times and became legends. She was spotted out with Sinatra and it is alleged that they had a romantic relationship.

4. Lauren Bacall


Sinatra was very close to Lauren Bacall. Humphrey Bogart, Sinatra’s friend and workmate, believed that he was in love with Bacall and failed to attend the Sands on Bacall’s 32nd birthday out of jealousy, though the two men were on good terms. Sinatra and Bacall were frequently seen together in public throughout 1957. On March 11, 1958, they reportedly became engaged, though Sinatra denied intending to marry her.

5. Gloria Vanderbilt


Gloria Vanderbilt was an American artist, author, actress, heiress, and socialite. She has a long list of famous lovers: Howard Hughes, Marlon Brando, Errol Flynn, and Frank Sinatra. For her, Frank was a wonderful friend and an absolutely extraordinary person in her life.


6. Marilyn Monroe


Sinatra met Monroe in 1954. That time, he was still married to Ava Gardner. Ava’s ex-husband Joe DiMaggio was Sinatra’s friend. In the summer of 1961, Sinatra saw Monroe again and began an affair with her, and Monroe talked about marrying Sinatra, but he broke off the affair in fall of 1961, the same time he met Juliet Prowse.

7. Juliet Prowse


Juliet Prowse was an Anglo-Indian dancer. She was engaged to Sinatra for a short while from fall 1961 to early 1962 before Sinatra broke the engagement later that year because Prowse refused to give up her career.

8. Natalie Wood


In their film entitled Kings Go Forth, the character of Sinatra falls in love with Wood’s character. Rumors were spread that their relationship continued behind the scenes. It was also reported that Natalie had a serious relationship with Sinatra when she was just 15 years old.

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