Frank Sinatra had many close relationships throughout his life. He was married four times and had at least six other notable relationships in between. He had three verified children, as well as more than one of questionable paternity.

Marriages

Nancy Barbato

Frank Sinatra met Nancy Barbato (1917–2018) in the summer of 1934, and they married on February 4, 1939, in Jersey City, New Jersey, Barbato's home town.The Rough Guide to Frank Sinatra, Chris Ingham, pg 9 The wedding was held at Our Lady of Sorrows Church at 93 Clerk Street, after which the newlyweds lived in an apartment house at 137 Bergen Avenue. Their first child, 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. Both were born at the Margaret Hague Hospital in Jersey City."Frank Sinatra's Jersey City Connection", CityofJerseyCity.org. Accessed June 30, 2008.

Following the family's move to Hollywood, Sinatra began engaging in extramarital affairs, the first known with Marilyn Maxwell. 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.Ingham, pg 10, as related in Tina Sinatra's memoir A third child, Christina Sinatra, known as "Tina", was born on June 20, 1948.

The couple announced their separation on Valentine's Day, February 14, 1950, with Sinatra's additional extramarital affair with Ava Gardner compounding his transgressions and becoming public knowledge. After originally just seeking a legal separation, Frank and Nancy Sinatra decided some months later to file for divorce, and this divorce became final on October 29, 1951. Frank Sinatra's affair and relationship with Gardner had become more serious, and she later became his second wife.

Less widely known were Sinatra's continuing visits, his long, confiding late-night phone calls, and the convivial family dinners on birthdays, holidays and other occasions. "Throughout the many years after they split, my grandfather came to visit whenever his crazy life would allow it," Mrs. Sinatra's granddaughter AJ Lambert wrote in a 2015 remembrance in Vanity Fair. "I can remember times when she would be on the phone with her ex-husband, and the next thing I knew some eggplant was coming out of the freezer to thaw so that she could make him some sandwiches when he showed up." She remained profoundly private, uttering barely a word in public about her life with Sinatra, though their mutual feelings were clear, her granddaughter recalled, to those who knew them best. "I know he never stopped loving her," Lambert wrote. "And I know she never stopped loving him."

Nancy Barbato Sinatra died in 2018 at the age of 101. She never remarried and had outlived not only her ex-husband but also her son Frank Jr., who died in 2016.

Ava Gardner

Biographer Kitty Kelley claims that Sinatra had first seen photographs of Ava Gardner in a magazine and had sworn that he would marry her. Ruth Rosenthal, a friend of Gardner's, stated that Gardner initially detested him upon meeting him at MGM, finding him to be "conceited, arrogant and overpowering". Their similarities, however, from vices like smoking, drinking hard liquor and cursing, to their volatile tempers and love of violent sports, soon became apparent. Sinatra separated from Nancy on Valentine's Day 1950, after he confessed to his passionate affair with Gardner, and she subsequently locked him out of the house and hired a lawyer. Although Nancy initially refused to divorce him, Sinatra was eventually granted a divorce in Nevada in October 1951, and subsequently obtained a marriage license in Pennsylvania, marrying Gardner in a small ceremony on November 7, 1951. Following a turbulent marriage, with many well-publicized fights and altercations and an abortion in November 1952, the couple formally announced their separation October 29, 1953 through MGM.

Gardner filed for divorce in June 1954, at a time when she was dating matador Luis Miguel Dominguín, but the divorce was not settled until July 1957. Sinatra blamed Peter Lawford, who had dated Gardner before, for the split, and it took six years for Sinatra to forgive him. He was inconsolable in the fall of 1953 after the split, and according to Kelley, on November 18, Jimmy Van Heusen found him in the elevator of his 57th Street apartment with his wrists slashed. After the divorce, Sinatra continued to feel very strongly for Gardner and they remained friends for life. Additionally, Sinatra took responsibility for Gardner's business affairs long after the split, and was still dealing with her finances in 1976. When she fell into ill health in later years, Sinatra paid $50,000 towards her medical bills. Gardner's power in Hollywood helped Sinatra get cast in From Here to Eternity (1953) and his subsequent Academy Award for Best Supporting Actor helped revitalize Sinatra's film career.Ingham, pg41

Mia Farrow

Sinatra married actress Mia Farrow on July 19, 1966, when she was 21 and he was 50. At the time, Sinatra was enjoying a wave of renewed popularity as the song "Strangers in the Night" returned him to the top of the Billboard charts only seventeen days later. They met on the set of Sinatra's film Von Ryan's Express.Ingham, p. 80 She agreed to appear in his 1968 film The Detective, but when she reneged as her filming schedule for Rosemary's Baby overran, Sinatra served her divorce papers in front of the cast and crew;Ingham, p. 81 they were divorced in Mexico in August 1968. In an interview for the November 2013 issue of Vanity Fair, Farrow said that she and Sinatra "never really split up" and answered "possibly" when asked if her son Ronan might be Sinatra's."Exclusive: Mia Farrow and Eight of Her Children Speak Out on Their Lives, Frank Sinatra, and the Scandals They've Endured" . Vanity Fair. October 2, 2013.

Barbara Marx

On July 11, 1976, Sinatra married Barbara Marx (formerly married to Zeppo Marx, the straight man in the Marx brothers' actNash, Eric P. "Books in Brief: Nonfiction", The New York Times, February 18, 2001. Accessed January 7, 2008. "Sinatra's last wife, Barbara Marx, who had been married to Zeppo, the unfunny Marx brother, is depicted as the wicked stepmother, isolating the aging star from friends and family, persuading him to change his will and failing to notify the children in his last hours."), who converted to Catholicism to marry him. 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 Frank was close to his death, although they were close by, and the children missed the opportunity to be at their father's bedside when he died.

In 2021, an unknown individual vandalised Sinatra's grave marker, attempting to chisel away the word "husband". The damaged marker was replaced with a new one with the words, "Sleep warm, poppa", the same words that his daughter Tina had buried with him.

Relationships Sinatra had numerous extramarital affairs, the first of which was with blonde starlet Alora Gooding from October 1940 while in Hollywood, his "first big love away from home", according to Nick Sevano. Next followed Rita Maritt, a 16-year-old Long Island debutante; the daughter of an oil baron; and Mary Lou Watts, a wealthy socialite. Gossip magazines published details of affairs with the likes of Lana Turner and Marilyn Maxwell.

Lana Turner Summers and Swan claimed that Turner had gushed of a "very serious affair" between the two, and that they had faked splitting up their relationship just to oblige MGM's concerns. Turner later denied the claims in her 1982 autobiography, saying that "the closest things to dates Frank and I enjoyed were a few box lunches at MGM".

Judy Garland

Sinatra and Judy Garland remained good friends 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). 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.

Lauren Bacall Sinatra was very close to Lauren Bacall. 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. Sinatra and Bacall were frequently seen together in public throughout 1957, and on March 11, 1958, they reportedly became engaged, though Sinatra denied intending to marry her.

Juliet Prowse

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.

Marilyn Monroe

Sinatra met Marilyn Monroe in 1954 while he was still married to Ava Gardner, although some sources suggest they may have first met earlier. He was a friend of Monroe's second husband, Joe DiMaggio. Following DiMaggio and Monroe's divorce, Sinatra accompanied DiMaggio and writer James Bacon to investigate rumors that Monroe was seeing her vocal coach Hal Schaefer. The group mistakenly entered the apartment of another woman, Florence Kotz, in what later became known as the "wrong door raid".

Accounts differ regarding the nature of Sinatra's later relationship with Monroe. Some sources claim they had a brief romantic involvement during the summer of 1961, while others describe them primarily as close friends. However, the extent of their relationship remains unclear, and most reputable biographers consider assertions of a serious affair or discussions of marriage to be unsubstantiated and largely speculative.

Angie Dickinson

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. The two remained friends until Sinatra's death in 1998.

Children Sinatra had three children with his first wife, Nancy Barbato: Nancy Sinatra (born June 8, 1940), Frank Sinatra Jr. (January 10, 1944 – March 16, 2016), and Christina "Tina" Sinatra (born June 20, 1948). Although Sinatra did not remain faithful to his wife, he was by many accounts a devoted father.

On December 8, 1963, Frank Sinatra Jr. was kidnapped. Sinatra paid the kidnappers' $240,000 ransom demand (even offering $1,000,000, although the kidnappers bizarrely turned down this offer), and his son was released unharmed on December 10. (In 2022 terms, the demand would be the equivalent of $2.32 million, and the amount Sinatra offered would be equivalent to $9.68 million.) Because the kidnappers demanded that Sinatra call them only from pay phones, Sinatra carried a roll of dimes with him throughout the ordeal, and this became a lifelong habit. The kidnappers were subsequently apprehended and convicted. A 2003 movie called Stealing Sinatra was made about the incident. The radio program This American Life interviewed one of the kidnappers, Barry Keenan, in the 2002 episode "Plan B".