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Sinatra and Judy Garland remained good friends up until her death in 1969, but on only two occasions were the two legendary singers romantically involved.The first was in 1949, when Garland was recovering from a nervous breakdown and the two went on a romantic rendezvous in the Hamptons (Garland was still married to director Vincente Minnelli).Sinatra was romantically involved with Angie Dickinson off and on for ten years from around 1954 to 1964."We had an incredible 'like' for each other" and "a very comfortable relationship", stated Dickinson in 1999, adding that if they'd had "a burning love affair" then the romance might not have lasted as long.Frank Sinatra's affair and relationship with Gardner had become more and more serious, and she later became his second wife.Sinatra later expressed regrets at having married Nancy saying "What I had mistaken for love," he ruefully stated later, "was only the warm friendship Nancy had brought me." Kitty Kelley claims that Sinatra had first seen photographs of Ava Gardner in a magazine and had sworn that he would marry her.Both children were born at the Margaret Hague Hospital in Jersey City.Following their move to Hollywood, Los Angeles, California, Sinatra errantly strayed from his marriage into extra-marital affairs, the first known with Marilyn Maxwell.

Sinatra had just come off his messy separation from Ava Gardner and was spotted in Garland's company until Luft found out. According to Kelley, her husband Humphrey Bogart believed that Sinatra 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.

He was inconsolable in the fall of 1953 after the split, and according to Kelley, on November 18, Van Heusen found him in the elevator of his 57th Street apartment with his wrists slashed.

Sinatra married actress Mia Farrow on July 19, 1966, when she was 21 and he was 50.

Winslet was previously asked about working with Allen in the wake of the accusations levelled against him and she told the New York Times, "As the actor in [Wonder Wheel], you just have to step away and say, I don’t know anything, really, and whether any of it is true or false.

Frank Sinatra had many close relationships throughout his life.She remained his wife until his death, although her relations with Sinatra's children were consistently portrayed as stormy, something Nancy Sinatra confirmed when she publicly claimed that Barbara had not bothered to call Frank's children even when the end was near, although they were close by, and the children missed the opportunity to be at their father's bedside when he died.