Sinatra first met Ava when she was better known as Mrs. Mickey Rooney. Ava and Mickey were at the Mocambo Club on the Sunset Strip where Frank was performing in 1942. After his performance was over, he quickly set his sights on Ava. He made his way to her through the audience, unveiled that big grin. "Hey, why didn't I meet you before Mickey? Then I could have married you myself," he said. Ava was speechless. At the time, she had not yet become "Ava Gardner, the most beautiful woman in the world." She was still just a contract player on the Metro-Goldwyn-Mayer back lot, and just a little over a year removed from rural North Carolina. However, Ava knew of Frank’s reputation and wasn’t impressed.

On the other hand, he was Frank Sinatra. Not yet the Chairman of the Board, but well on his way to superstar status. Legions of bobby-soxers across the nation had propelled him from a skinny little singer from New Jersey with the Harry James Orchestra to the top-selling crooner in the nation.

Always the engaging flirt, Frank tried his luck at winning Ava's heart on other occasions after she had divorced Rooney. Ava, like hundreds of other young girls at the time, was intoxicated by Sinatra's distinctive voice. She always had a thing for musicians. Her next husband, band leader Artie Shaw, is a testament to that obsession.

By the end of World War II, Sinatra had a bachelor pad at the Sunset Towers, which literally towered over the small apartment house Ava was renting at the time. During the occasional party with friends, Sinatra would go out of the balcony and shout out to Ava with a boozy voice.

One day outside her apartment, she finally accepted his invitation out to dinner. But dinner was all it was. He tried his hardest to charm her, but she was still able to resist him. Ava just couldn't bring herself to ignore the fact that Sinatra was a married man. Her upbringing was making it difficult for Ava to follow her heart - for the moment. It wasn't until 1949 when Ava met Sinatra at a party in Palm Springs that he began to make any headway toward winning her heart. Ava fell head over heels for him that night, but otherwise his luck had already started to change. Ava realized he was a married man, with three children, no less, but the gossip columns had reported he was leaving his wife Nancy for good. At the same time, he was losing his voice, hadn't had a Number 1 record in a while, and had even lost top billing to Gene Kelly in their MGM film "On the Town." He was also about to begin a disappointing career in television. But at this point, she was completely under his spell. "Oh, God, he could be the sweetest, most charming man in the world when he was in the mood," she said.

Sinatra told Ava it had been over with him and Nancy for years, but his three children were another matter. He would stay committed to them for the remainder of his life. But Lana Turner warned Ava that he had told her the same thing a few years earlier. "I really liked Lana. She was a nice girl, and she felt neither malice nor anger toward Frank and me," Ava recalled in her autobiography. "She just thought I ought to know. I told Lana gently that Frank and I were in love, and that this time he really was going to leave Nancy for good. If I'm in love, I want to get married: that's my fundamentalist Protestant background. If he wanted me, there could be no compromise on that issue."

Frank and Ava still had a number of other romances in their lives, but he especially found fault with eccentric billionaire Howard Hughes, who had become increasing obsessed with Ava over the years. Hughes himself didn't like Ava cavorting around with Howard Duff and Robert Taylor, much less Sinatra. Like Lana Turner, Hughes warned Ava about falling for the infamous womanizing Sinatra.

Frank and Ava tried to keep a low profile. Ava had a moral clause in her contract, so they had to keep their affair secret for as long as possible. As their love grew, the couple's hate for the media grew as well. They were the hot story, and the gossip columns were relentless in their pursuit. Despite the press onslaught Nancy wouldn’t grant Sinatra a divorce so he was free to marry Ava. Whilst Sinatra and Ava were conducting their affair, due to the international media exposure, many people in society looked down upon the pair for their behaviour and Sinatra’s treatment of his wife. Their affair was one of the biggest scandals of Sinatra’s life, romantically speaking. Ava received letters of abuse from all around the world from mothers to school children.

In 1950 on Valentines Day, the separation was announced between Nancy and Sinatra. One and a half years later, the divorce was final. During this time, Frank's contract with MGM was cancelled, due to his behaviour, and wasn't renewed until he filmed, "The Tender Trap" with Debbie Reynolds.

Nancy agreed to a divorce one and a half years after they separated, and Ava and Frank were married on November 7, 1951. She was bombarded with hate mail, but her film career never suffered. Their careers at this point were headed in completely different directions now. Many fans turned their back on Sinatra since the Catholic father of three had left his wife for a glamorous movie star. He soon found himself bankrupt and without contract with MGM or Capitol Records. He was forced to borrow money from Ava to buy his children Christmas gifts. The proud Italian could not accept the fact that his wife was the bread winner.

During their tumultuous marriage, the reversal of fortune between their careers was becoming more and more apparent to the world. The publicity guys at MGM took a quote from Ernest Hemingway and had christened Ava "the most beautiful animal in the world." While Ava had become one of Hollywood's brightest stars, Sinatra found himself at the low point of his own career. It was not good for the marriage. She was a female Frank Sinatra and they just clashed at every turn - too stubborn and headstrong to live in harmony for long. Gossip columnists snidely referred to Sinatra as “Mr. Ava Gardner” due to the career slump he found himself in at that point in his life, which didn’t sit well with him.

Ava knew things wouldn't get better unless Frank could make a comeback. Columbia was developing a film version of "From Here To Eternity." Frank wanted the part of Maggio, a head-strong skinny Italian, he was born to play. Ava lobbied the producers of the film to cast him in the role. The only problem was character actor Eli Wallach had already been cast in the role. The producers viewed a screen test Sinatra provided, a rarity in those days for a star of his stature, but he had taken a great fall. Columbia offered him the role for a measly $8,000, which he accepted. His portrayal of Maggio won him an Academy Award for Supporting Actor and saw his career back on track, his marriage, however was in trouble.

Amazingly, their notorious public quarrels were never professional in nature. Both Ava and Frank, known for having a number of love interests, were constantly fighting about the other's wandering eyes. The media just fed the fire. Their fiery temperaments were constantly at odds with each other. They knew how to push each others buttons. They would learn to zero in on each others insecurities and then use them against each other in fierce battle. When Ava had an abortion without even informing Frank she was pregnant, the marriage would never be the same. When Sinatra and Gardner finally separated in 1953, Sinatra fell into a deep depression. He still loved her and was insanely jealous of any man who was with her. Peter Lawford is quoted as saying, "Ava and Frank had a great romance but neither of them had the self confience to handle it." The couples Mexican divorced was granted in 1957 though the marriage had been over years earlier. In the end they were too much alike to stay together. Years later, Ava confessed that despite the number of men she loved, Frank was by far the "love of her life."

It’s widely believed that Gardner was the great love of Sinatra’s life. Perhaps more accurately, she was the great obsession of his life. He loved her madly and couldn’t live without her, despite the legendary fights, resulting in hotel rooms being trashed and furniture demolished. After their split, Frank vowed never to let another woman get as close to him as Ava was.

On July 19, 1966, Mia Farrow became Mrs. Sinatra #3 during a private wedding in Las Vegas. She was in her 20s, and Frank was in his 50s. Sinatra was pleased at her decision to give up acting to concentrate on her life with Sinatra, as he didn't want to have to depend on his wife financially. They divorced in 1968. Barbara Marx, a former Las Vegas show girl and former wife of Zeppo Marx became the fourth and final Mrs. Frank Sinatra on July 11, 1976.

Sinatra still kept in contact with Ava up until her death, making sure as her health failed, that she received the best care possible.