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“Come fly with me, let’s fly, fly away….” With Frank Sinatra crooning those words in his dulcet tones, gazing with those piercing blue eyes, with a smirk just smug enough to walk the line between bad boy and angel, what woman from the '40s, '50s, or '60s could ever be able to resist him? Very few, as it turns out. Today we’ll be taking a look at all the romantic entanglements that shaped Frank Sinatra’s life. 1. Nancy Barbato From left: Frank Sinatra with his first wife, Nancy Barbato Sinatra and Pat O'Brien, ca. 1943 / Everett Collection Sinatra’s first love, Nancy Barbato and Frank met as teenagers and were married before the crooner had turned 24. Their marriage was initially blissful, and the couple was soon raising two children in their small apartment in Jersey City. But alas fame changes everything, and Sinatra’s star was burning brighter by the second. A move to Hollywood proved too much for the Sultan of Swoon’s already wandering eye, and he soon engaged in numerous extramarital affairs. When these extracurricular activities became known to the press, Barbato considered ending things, but it wasn’t until an ongoing tryst with Ava Gardner in 1950 that she finally had had enough and left Frank behind. However, Barbato never remarried, and their granddaughter claims the two never truly fell out of love. RELATED: What Willie Nelson Regrets About Working With Frank Sinatra 2. Lana Turner HONKY TONK, Lana Turner, 1941 / Everett Collection Speaking of affairs, after seeing Lana Turner’s 1946 movie The Postman Always Rings Twice Sinatra supposedly only had one reaction - “I have to have her.” But can you really blame him? It’s Lana Turner. And when Sinatra wanted something, he generally got it - within minutes he had Turner’s phone number and was arranging a date. According to Frank, the two had a very passionate affair, with him stating that he had never been with a woman quite as “carnal” as Turner. For her part, Turner denied the affair for years afterwards, writing in a 1992 biography that "the closest things to dates Frank and I enjoyed were a few box lunches at MGM." Hmm. Either Frank exaggerated completely or they were serving up a spicy Italian bite for lunch back in the day. 3. Ava Gardner MY FORBIDDEN PAST, Ava Gardner, 1951 / Everett Collection In his second wife Sinatra finally ran up against a woman who could match him step for step in drinking, partying, and of course, cheating. By the time Ava Gardner and Sinatra tied the knot in 1951, the young actress had already had two marriages and numerous affairs, and you can see where this is leading. To a happy, peaceful marriage? Nope. The union between Gardner and Sinatra was a short, tumultuous period brought to a close when Gardner started dating the most famous matador in Spain. Because of course, Sinatra was inconsolable at the split, reportedly being found with his wrists slashed in his 57th St apartment. Despite their turbulent relationship, the two remained close, and Sinatra even paid $50,000 towards Gardner’s medical bills as her health declined later in life. 4. Angie Dickinson RIO BRAVO, Angie Dickinson, 1959 / Everett Collection While not as passionate a love affair as some on this list, Sinatra’s relationship with Angie Dickinson lasted far longer than most of his other entanglements, as the two dated off and on for almost two decades. They met on the set of Dickinson’s first-ever show biz job, The Colgate Comedy Hour, and renamed their, uh, acquaintance when Dickinson played Sinatra’s wife in 1960’s Ocean’s 11. While not a super intense relationship, the two were always there for each other, with Dickinson stating that the two had a very big “like” for each other and that if they’d had a “burning love affair” then their association could never have lasted as long. It’s always nice to have a rebound ready. 5. Lauren Bacall HOW TO MARRY A MILLIONAIRE, Lauren Bacall, 1953. ©20th Century-Fox Film Corporation, TM & Copyright/courtesy Everett Collection It’s never a good idea to get involved with a friend’s wife, especially if that friend is a film legend and a man that you basically hero worship. But did that ever stop Swoonatra? Of course not. After his relationship with Ava Gardner soured in the mid-fifties, Sinatra reportedly took up with Lauren Bacall. The only problem with this neat little love story is that Bacall was married to Humphrey Bogart, one of Sinatra’s best friends. In 1956 Bogart skipped Bacall’s 32nd birthday at The Sands casino out of jealousy, and as 1957 progressed, Bacall and Sinatra were seen publicly more and more - not a great look seeing as how Bogart was currently bedridden, dying of throat cancer. The two even became engaged in 1958 - an engagement called off once the proposed union became public knowledge. Apparently, Sinatra couldn’t take the public outcry a marriage to his friend’s recent widow would cause. 6. Marilyn Monroe THE SEVEN YEAR ITCH, Marilyn Monroe, 1955. TM and Copyright ©20th Century Fox Film Corp. All rights reserved. Courtesy: Everett Collection If Marilyn Monroe and Frank Sinatra never got together it would have been a crying shame, because the world would have been deprived of the two biggest stars of their day shacking up. But for a long time, it looked like this dream pairing wasn’t to be, as the two were just good friends. They consoled each other after their respective divorces from Ava Gardner and Joe Dimaggio, even becoming roommates while keeping everything platonic. But then the inevitable happened, and Sinatra came out of his room to find Monroe standing in front of the fridge fully nude, trying to decide between grapefruit and orange juice. Apparently, they decided the share a meal instead. Despite the relationship not lasting very long, Sinatra was distraught after Monroe’s overdose death and barred from her funeral by former friend Joe Dimaggio. 7. Juliet Prowse Juliet Prowse, October 1965. ph: William Claxton / TV Guide / courtesy Everett Collection In the early '60s, Sinatra abandoned his pattern of dating Hollywood’s most famous leading ladies and instead became engaged to the young star of his new movie Can-Can, Juliet Prowse. Sinatra’s friends were initially surprised, with fellow Rat Pack member Sammy Davis Jr. supposing that this was his way of distracting himself from Marilyn. Whatever the reason for the two getting together, the marriage never happened and the engagement was called off after only a few months. The young South African starlet refused to give up her career to become the kind of stay at home wife Sinatra longed for, and for her part, Prowse didn’t fully realize what dating ol’ blue eyes would entail - she later stated that “after a few drinks he could be really difficult.” You don’t say. 8. Mia Farrow THE GREAT GATSBY, Mia Farrow, 1974 / Everett Collection If Sinatra’s engagement to Prowse shocked his friends, his marriage to Mia Farrow in 1966 shocked all of Hollywood. First of all, the Chairman of the Board was 50 years old, while Farrow at 21 was younger than Sinatra’s eldest daughter. Farrow was also a hippie flower child that was firmly rooted in a new generation of peace and love, while Sinatra was a gray-haired, chain-smoking, tuxedo-wearing, whiskey-swilling champion of a bygone era. The match was so out of leftfield that Sinatra’s ex-wife Ava Gardner remarked, “I always knew Frank would end up with a boy,” a cheap shot at Farrow’s pixie cut. Needless to say, the relationship did not last, with Farrow being served divorce papers in front of the whole cast and crew of her movie Rosemary’s Baby. Still, in 2013 Farrow said the two had “never really split up” and hinted that Sinatra was the real father of her child Ronan Farrow, born in 1987 20 years after their divorce. The blue eyes don’t lie. 9. Barbara Marx Barbara Marx Sinatra, Frank Sinatra at a celebrity golf tournament, February 1974 / Everett Collection In 1976 Sinatra was married again, this time to showgirl and socialite Barbara Marx, a woman who took her last name not from the German Karl, but rather from Zeppo Marx, her second husband and the straight man in the Marx Brothers. It was his fourth marriage, and her third, but both the last and longest for either one. Despite more than twenty years of matrimony, quite an accomplishment for these two, their relationship was far from perfect. The most obvious strain came from Marx’s inability to get along with Sinatra’s children from his marriage. The bad blood apparently went so deep that Marx didn’t inform Sinatra’s kids as he lay dying, and they lost the opportunity to be with their father on his deathbed. Harsh. However, it was Sinatra’s most successful relationship and the one that outlasted him. And there you have them! Some of the loves of Frank Sinatra’s life. Whether short flings or decades-long marriages, all of these ladies were sucked in by Sinatra’s massive, planet-like gravitational pull. How many do you remember the rattiest rat pack member dating? Who did we miss? Let us know in the comments below, we read every one!