Ol’ Blue Eyes Sure Got Around: Sinatra’s Many Lovers

Frank Sinatra was loved by many because of his music and of course his handsomely good looks. With hits such as “Fly Me To The Moon” and “You Make Me Feel So Young,” Sinatra was a favorite with fans — especially of the female persuasion.

The number of lovers in his life is staggering with many well-known actresses topping the list. Whether it was Blue Eyes charm or his melodic singing voice, the women just seemed to flock to him and he graciously accepted their advances, dating one right after another. While some of his love interests made headlines, others didn’t and are known to be true only through rumors in the industry.

While some of these women on our list won’t surprise you, you won’t believe who Sinatra’s most recent lover was. This famous supermodel is quite a bit younger than Sinatra and was probably as surprised by the tryst as much as you are.

Gloria Vanderbilt

Image Source: Wikimeda Commons
Image Source: Wikimeda Commons

Among Gloria Vanderbilt’s list of famous lovers is Sinatra. Vanderbilt has been quite open and public about the relationship whenever asked about it. She has even written about her tryst with Sinatra in a book titled The Rainbow Comes And Goes and discussed it in her documentary “Nothing Left Unsaid.”

Lauren Bacall

Image Source: Wikipedia
Image Source: Wikipedia

While married to Humphrey Bogart, Lauren Bacall started an affair with Sinatra after learning that Bogart was having an affair with his secretary. Both Bacall and Sinatra remained together through Bogart’s death. They went public with their relationship after Bogart died. Unfortunately, they were not able to make the relationship last.

Grace Kelly

Image Source: Wikipedia
Image Source: Wikipedia

Starring in the movie “High Society” together, both Grace Kelly and Sinatra had a love affair off screen. Kelly was married to George Jacobs at the time and was rumored to have had several affairs behind his back. Jacobs has acknowledged the Princess of Monaco’s affair with Sinatra but said he didn’t know about it at the time.

Judy Garland

Image Source: Wikipedia
Image Source: Wikipedia

Judy Garland and Sinatra shared the big screen in several films which transitioned to a romance on two occasions. Once was while Garland was married to Vincent Minelli after reportedly having a nervous breakdown and the other while she was separated from her husband at the time, Sid Luft.

Natalie Wood

Image Source: Wikipedia
Image Source: Wikipedia

Natalie Wood was only 15 years old when she reportedly had a serious relationship with Sinatra. Meeting on the film “Kings Go Forth,” the two began dating and went on to continue their steamy relationship well after the film ended. While their romance didn’t last, the two remained close friends for many years.

Angie Dickinson

Image Source: Wikipedia
Image Source: Wikipedia

With a romance that extended on and off for 20 years, it’s safe to say that Angie Dickinson was one of Sinatra’s favorite. He liked her so much he kept going back to her. While Dickinson played Sinatra’s wife in the movie Ocean’s Eleven, the two never married – only always dating.

Marilyn Monroe

Image Source: Pixabay
Image Source: Pixabay

Surely you heard about Marilyn Monroe and Sinatra, but what you probably haven’t heard is that Sinatra wanted to save Monroe from her drug problem and foreseeable death. He asked her to marry him, but she declined and later fulfilled his prophecy by succumbing to a drug overdose that still raises questions to this very day.

Zsa Zsa Gabor

Image Source: Wikipedia
Image Source: Wikipedia

Meeting at a party they were both attending, Zsa Zsa Gabor and Sinatra were lovers for a short period of time. Although the time they were together was brief, it was said that the relationship quickly heated up between Sinatra and the Hungarian actress and socialite, but not enough to make Sinatra one of Gabor’s 10 husbands.

Joan Crawford

Image Source: Wikipedia
Image Source: Wikipedia

Though this love interest has been neither fully confirmed or denied, Joan Crawford has been rumored to have dated Sinatra. The Mommy Dearest star was spotted with Sinatra on several occasions making the rumor seem true. We’ll just have to speculate as Sinatra took the secret to his grave along with Crawford who died in 1977.

Donna Reed

Image Source: Wikimedia Commons
Image Source: Wikimedia Commons

Things heated up between Donna Reed and Sinatra on the set of “From Here To Eternity,” where it is said the two got together during filming. Not much is known about this relationship between Sinatra and this wholesome housewife from “The Donna Reed Show,” but it has been confirmed on various occasions.

Shirley MaClaine

Image Source: Wikipedia
Image Source: Wikipedia

While the two were friends for many years, it is rumored that Shirley MaClaine and Sinatra also had a fling together. The two actors appeared in “Some Came Running” together. While the two are said to have gotten together, it didn’t last as both MaClaine and Sinatra decided to be just friends and remained so for many years to follow.

Lana Turner

Image Source: Wikipedia
Image Source: Wikipedia

Actress Lana Turner was blamed for breaking up Sinatra and his first wife Nancy Barbato. Sinatra apparently saw Turner in the “Postman Always Rings Twice” and proclaimed that he had to have her. He did and had an affair with Turner while he was married. He then asked Barbato for a divorce, while the media had a field day blaming Turner for the breakup.

Hedy Lamarr

Image Source: Wikipedia
Image Source: Wikipedia

This Austrian beauty is famous for inventing a radio guidance technology, but she was also a lover of Sinatra. The two dated in 1930 and Sinatra was said to have treated her different from any of his other conquests. The two appeared together on the cover of the Movie Story.

Jill St. John

Image Source: YouTube
Image Source: YouTube

Filming two movies together, “Come Blow Your Horn” and “Tony Rome,” Jill St. John and Sinatra were said to have gotten it on behind the scenes. The two dated in 1963, but St. John went on to marry Robert Wagner, who coincidently was married to Natalie Wood who also dated Sinatra.

Judith Exner

Image Source: Alchetron
Image Source: Alchetron

While more widely known for her affair with President Kennedy, Judith Exner also had a brief relationship with Sinatra. The two met through a family connection to the music industry. Sinatra actually brought Exner and Kennedy together when they met at one of his Vegas shows. The rest is history.

Lena Horne

Image Source: Flickr
Image Source: Flickr

This one is a rumor that is believed to be true but has never been confirmed by either party involved. Singer Lena Horne was said to have hooked up with Sinatra. The two worked in the music industry together so it could easily be true as Horne had a voice that would melt hearts, while Sinatra would have no doubt been a sucker the beautiful singer.

Ava Gardner

Image Source: Wikimedia Commons
Image Source: Wikimedia Commons

Sinatra met and fell immediately in love with actress Ava Gardner. They married in 1951 and stayed married for six years. The two consider each other great loves and have both regretted ending the marriage. The two remained close friends after the marriage and up until Sinatra death. Gardner has said he was the love of her life.

Mia Farrow

Image Source; Wikimedia Commons
Image Source; Wikimedia Commons

With a 30-year age difference, the two married and later divorced after Mia Farrow wanted to further pursue her career in acting. Sinatra didn’t want her to act and served her divorce papers while she was filming “Rosemary’s Baby” saying she was an impossible teenager. The divorce was finalized in 1968.

Barbara Marx-Sinatra

Image Source: Daily Mail
Image Source: Daily Mail

Considered the true love of his life, Sinatra married Barbara Marx-Sinatra after they were neighbors. This wasn’t their first meeting as the Vegas showgirl ignored him on their first encounter. Years later they found themselves rekindling the relationship. The two were married for 22 years. Marx-Sinatra penned a book about the relationship called “Mrs. Blue Eyes.”

Kate Moss

Image Source: Twitter
Image Source: Twitter

This one will probably surprise you but it’s true. Kate Moss met Sinatra at a party for his 80th birthday that she attended with her date Johnny Depp. Having his bodyguards circle around Moss so Deep couldn’t interrupt, Sinatra kissed her on the lips and then offered her a cigarette. Even at the age of 80, Sinatra was a lady’s man.