Random Fascinating Stories About Frank Sinatra's Personal Life (10 items)

(#3) People Talked About The Size Of His Endowment

It was no secret Sinatra was a ladies' man, and his former lovers had no qualms openly discussing his physical traits. Murray Garrett, a press photographer, recalled when reporters asked Ava Gardner about Sinatra.
One journalist quipped, "Hey Ava, Sinatra's career is over, he can't sing anymore - what do you see in this guy? He's just a 119-pound has-been," to which she replied, "Well I'll tell you - 19 pounds is c*ck."
(#10) He Had Extramarital Relationships

Sinatra was married four times throughout his life. He had a reputation of dating young starlets while married to his first wife, Nancy Barbato. He also attempted to leave her for Lana Turner.
Nancy eventually agreed to a divorce, and he left her immediately for his next wife, Ava Gardner. Neither were faithful to one another - and the cycle continued throughout his entire life.
Various publications and biographies claim Sinatra bedded some of the biggest stars in his prime. Marilyn Monroe, Grace Kelly, Lauren Bacall, Jackie Onassis, and Mia Farrow are just a few names on Sinatra's allegedly long list of partners.
(#8) He Despised Journalists But Still Had Romantic Affairs With Them

Despite his active social life, Sinatra was a very private person. It was no secret that he despised journalists, especially those looking for sordid details of his life. Still, Sunday Mirror reporter Sandra White claimed she was once invited up to Sinatra's hotel suite for a romantic evening. White wrote a book, Strangers In The Night: My Secret Weekend With Frank Sinatra, in which she details the evening:

By now it was 1 am, and with the other guests wandering off to bed and Barbara to her own separate suite, Frank asked me to join him for a nightcap in his private suite.

That’s where I came to be holding hands with him on the sofa. His voice was soft, smooth and sensual. Did I fancy him? Absolutely no doubt.

Even though he was 72 and I was then 38, he was still a very sexy man. Still handsome, still desirable. He even smelled sexy. He breathed sex in my ear!
(#4) Paul Anka Claimed Sinatra Hosted Wild Vegas Parties

In his memoir, My Way, Canadian crooner Paul Anka talks about Sinatra at length, specifically about when he first met Sinatra in Vegas in 1960. Anka wrote what is arguably Sinatra's biggest hit, "My Way," and saw behind the facade of the Rat Pack.
"From the first time I heard about the Rat Pack, I wanted to be around these guys and amazingly, they took me in," Anka wrote. In his memoir, Anka details the parties Sinatra and his crew threw in Las Vegas. The stars socialized in steam rooms with fans, especially young women. According to Anka, massage rooms were available in case any of the men "wanted to take advantage," of the swooning fans.
Anka also claims President John F. Kennedy partook in said events: "I saw the reality: Kennedy and the hookers, the women who hung around Frank, and the mob... The things I saw and witnessed, it was all part of show business, but it was pretty wild. All the JFK escapades with show girls happened in Vegas."
(#5) He And Dean Martin Labelled Angie Dickinson As Their Favorite Bedfellow

In Paul Anka's memoir, he also claims both Sinatra and fellow Rat Pack member Dean Martin bedded actress Angie Dickinson. When casino owner Steve Wynn asked Sinatra which woman was best in bed, Sinatra answered with, "Angie!" Martin agreed.
Dickinson and Sinatra had a 20-year on-and-off relationship which began in 1953 after Sinatra's bodyguard asked Dickinson to join him in his dressing room. At a 2015 TCM event, Dickinson said she knew Sinatra was "famous for having sex with his leading ladies," but did not comment any further on their relationship.
(#6) He Had High Expectations Of The Women In His Life

Sinatra was not a fan of ostentatious women who wore elaborate perfumes or flashed what he deemed an excessive amount of skin. He hated smoking and was known for being a stickler for well-groomed ladies, particularly paying attention to their hair and hands.

Sinatra focused his sights on what he considered "classy" women - women who kept it natural yet beautiful. His standards went well above just craving these things in a woman, though. He was known to kick girlfriends out if they showed up wearing perfume.