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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.

Their wedding was held at Our Lady of Sorrows Church at 93 Clerk Street, after which the newlyweds resided in an apartment house at 137 Bergen Avenue.

Their first child, their elder daughter Nancy Sinatra, was born on June 8, 1940, and their son, Francis Wayne Sinatra, known as Frank Sinatra, Jr., was born on January 10, 1944.

Sinatra was also engaged to India-born South African actress and dancer Juliet Prowse for a short while from fall 1961 to early 1962, before Sinatra broke the engagement late that year because Prowse refused to give up her career.

The two first met on the set of the 1960 film Can-Can.

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Frank Sinatra had many close relationships throughout his life.

The second was during one of Garland's many separations from her third husband Sid Luft in 1955.

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.

These affairs also became public knowledge and caused great embarrassment to Nancy Barbato Sinatra, who considered calling off their marriage then and had an abortion when she became pregnant in 1946.

A third child, Christina Sinatra, known as "Tina", was born on June 20, 1948.

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