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Frank Sinatra Dating History

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Complete list of Frank Sinatra dates, listed in chronological order.

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Anne Baxter
Anne Baxter and Frank Sinatra unknown date
Jacqueline Park
Jacqueline Park and Frank Sinatra unknown date
Lee Remick
Lee Remick and Frank Sinatra unknown date
Sheila MacRae
Sheila MacRae and Frank Sinatra unknown date
Carol Lynley
Frank Sinatra and Carol Lynley unknown date
Martha Hyer
Martha Hyer and Frank Sinatra unknown date
Vicki LaMotta
Vikki LaMotta and Frank Sinatra unknown date
Knockout! The Sexy, Violent, Extraordinary Life of Vikki LaMotta By Vikki LaMotta and Thomas Hauser ..............Alone and working as a chorus girl to support three young children, she dated Johnny Carson, was pursued by Frank Sinatra, and became the lover of mob boss Sam Giancana........... [more]
Nancy Berg
Nancy Berg and Frank Sinatra unknown date
In the book Model: The Ugly Business of Beautiful Women, Nancy names Sinatra as one of her dates/lovers. [more]
Judy Campbell
Judy Campbell and Frank Sinatra unknown date
Judi Meredith
Judi Meredith and Frank Sinatra unknown date
Betty Kelly
Betty Kelly and Frank Sinatra unknown date
Lena Horne
Frank Sinatra and Lena Horne unknown date RUMOR
Frank tried to make a play for her and failed. Lena was a true lady in every sense of the word. [more]
Zsa Zsa Gabor
Frank Sinatra and Zsa Zsa Gabor 1931
Zsa Zsa claims to have hated Sinatra and slept with him only because he refused to move his car out of a driveway unless she did. [more]
Nancy Barbato
Frank Sinatra and Nancy Barbato February 1934 - October 1951
Sinatra met Barbato at the age of nineteen, and they were married on February 4, 1939 in Jersey City, New Jersey, Barbato`s home town. The wedding was held at Our Lady of Sorrows Church at 93 Clerk Street, after which time the couple resided in an apartment at 137 Bergen Avenue. Their first child, Nancy ... [more]
Marlene Dietrich
Frank Sinatra and Marlene Dietrich 1944
Dietrich was 44, 14 years Frank’s senior. One of her diary entries suggests that they knew each other as early as 1942, and they were evidently close two years later. “I know they had a thing going,” said Frank’s songwriter Sammy Cahn. “She would have been difficult to ... [more]
Lana Turner
Frank Sinatra and Lana Turner 1946 - 1947
One of the women was to be Lana Turner, Warner Brothers’ Sweater Girl and then screen star. They met in Hollywood in 1940 and intimacy probably came later in 1946 when they began a dalliance at the MGM studio. “They used to smooch in his car parked on the lot,” an MGM executive said ... [more]
Judy Garland
Frank Sinatra and Judy Garland 1948 - October 1951
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 ... [more]
Ava Gardner
Frank Sinatra and Ava Gardner August 1949 - July 1957
Sinatra first met Ava Gardner in 1945, but saw her only sporadically until late 1949, when they began their relationship. Their relationship was extremely tempestuous, and coincided with the collapse of Sinatra`s professional career, as Gardner`s blossomed. They married on November 7, 1951, ten days ... [more]
Grace Kelly
Frank Sinatra and Grace Kelly 1954
Though his love life was hardly a secret, during the Gardner saga Frank issued what the press dubbed “Sinatra’s law,” an edict that held that his private affairs were off-limits. In late 1954, he made a play for Grace Kelly. Though involved with another man, and in spite of the lasting ... [more]
Gloria Vanderbilt
Frank Sinatra and Gloria Vanderbilt 1954
His valet, George Jacobs, thought Frank “craved class” in women. Socially, no one could have been classier than the heiress Gloria Vanderbilt. Thirty-one when she and Frank got together in late 1954, she had come into a fortune — some $27 million in today’s dollars — and ... [more]
Angie Dickinson
Frank Sinatra and Angie Dickinson 1954 - 1964
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 ... [more]
Eva Bartok
Eva Bartok and Frank Sinatra 1956 - 1957
Some three decades late, Bartok claimed that her daughter, Deana, born in 1957 was actually fathered by Frank Sinatra during a brief affair that Bartok and Sinatra had in 1956. [more]
Joan Blackman
Frank Sinatra and Joan Blackman December 1956
Was spotted on a date going to the premier of in 1956 Anastasia [more]
Jeanne Carmen
Jeanne Carmen and Frank Sinatra 1957 - 1960
on-again-off-again 1957 - 1960 1957 sends a revealing pic of herself to Frank Sinatra. Sinatra answers promptly. September 58 she and Pete Rugulo are in a large group with Frank Sinatra partying at Dean’s Sunset Strip restaurant November 58 columnist Earl Wilson reveals: “Jeanne Carmen ... [more]
Lauren Bacall
Frank Sinatra and Lauren Bacall April 1957 - March 1958
Later, Humphrey Bogart fretted about his wife Lauren Bacall’s relationship with Frank. When Frank arranged a birthday party for Bacall in Las Vegas, in September 1956, her husband stayed away. He was “edgy and resentful” when she got home and she soon found out why. “He was s ... [more]
Venetia Stevenson
Venetia Stevenson and Frank Sinatra December 1957
Adelle Beatty
Adelle Beatty and Frank Sinatra 1958 - 1960
Tuesday Weld
Frank Sinatra and Tuesday Weld 1959
1959 rumors circulate that she's dating Frank Sinatra and Raymond Burr [more]
Juliet Prowse
Frank Sinatra and Juliet Prowse 1959 - February 1975
This couple dated on and off for over a decade. Frank met dancer Juliet Prowse on the set of Can-Can in 1959. She was 23 to his 44, a tall, intelligent, brilliant dancer. Frank seemed “amazingly kind and gentle”. Maybe it was because she was close to his daughter’s age. There were ... [more]
Marilyn Monroe
Frank Sinatra and Marilyn Monroe February 1959 - August 1961 RUMOR
Sinatra and Monroe. Here were stars who shone with equal brilliance. It seems clear that there was some sort of affair, at a time when Marilyn was an emotional basket case. Frank had become solicitous during the collapse of her marriage to Arthur Miller. He presented her with a white poodle that she ... [more]
Kipp Hamilton
Frank Sinatra and Kipp Hamilton June 1959 - November 1960
June 59 Gina Lollobrigida is reported "toasting temperamental tizzies over Kipp Hamilton's added scenes with Frank Sinatra" on MGM's Never So Few soundstage Winchell thinks Sinatra's "date last week with starlet Kipp Hamilton 'worked.' It won her back the real love ... [more]
Keely Smith
Keely Smith and Frank Sinatra 1961
Keely was linked romantically with her sometime duet partner Frank Sinatra: She states,“I almost married Frank. He was a wonderful man, but we lived different lifestyles. Frank was on the fast lane and I was still a v*rginia girl.” [more]
Mia Farrow
Frank Sinatra and Mia Farrow July 1964 - August 1968
(19 July 1966 - 16 August 1968) (divorced) Mia Farrow met Frank in 1964 at 20th Century Fox, when she was playing the lovelorn daughter in the TV version of the novel Peyton Place. She was no stranger to the ways of Hollywood and New York but looked the part of the innocent waif. Press speculation about ... [more]
Natalie Wood
Frank Sinatra and Natalie Wood 1966
Natalie had an on and off affair with Frank, according to Suzanne Finstad's biography of Wood. [more]
Irene Tsu
Frank Sinatra and Irene Tsu November 1968 - 1969
November 68 Frank Sinatra is reported escorting Tsu and Quinn O'Hara August 69 Tsu will star with Frank Sinatra in an espionage tale to be filmed in Hong Kong December 69 columnist Marilyn Beck reports about Ava Gardner's upcoming visit to Hollywood: "You can bet Frank Sinatra ... [more]
Victoria Principal
Frank Sinatra and Victoria Principal 1972
Ole twinkle toes Frank Sinatra is said to have shuffled his way into an encounter with actress Victoria Principal. She’s one of a long list of women said to have had sex with the Chairman of the Board [more]
Hope Lange
Frank Sinatra and Hope Lange 1972
In 1972 she also dated Frank Sinatra [more]
Elizabeth Taylor
Frank Sinatra and Elizabeth Taylor 1974
Frank Sinatra dated Elizabeth Taylor in 1961. [more]
Barbara Marx
Frank Sinatra and Barbara Marx January 1976 - May 1998
In 1976, 16 years after their first meeting, Frank proposed to Barbara Marx, the ex-wife of Zeppo, the youngest of the Marx Brothers. The marriage, on July 11, was a grandiose affair at the home of the former ambassador Walter Annenberg. The guests included Ronald Reagan — he interrupted his p ... [more]

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Jennifer Garner attends Premiere Of Summit Entertainment's 'Draft Day' at Regency Bruin Theatre on April 7, 2014 in Los Angeles, California
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