Carole was a hopeless romantic who spent her entire life searching for true love. She married four husbands and dated some of Hollywood's most eligible bachelors. One magazine called her "Hollywood's Most-Dated Starlet". Here are some of the men she loved ....
Carole was briefly engaged to screenwriter and producer Gene Markey. He was twenty-three years older than her and had been married to Hedy Lamar. They started dating casually in 1941. She said "Gene Markey gives me books of plays to read, books about the
theater; he talks to me about the theater and gives me the feeling we
are talking about it". Gene gave Carole her beloved Great Dane Donner. Their relationship got serious in the Spring of 1942 and they were engaged for a short time. When the press announced they were getting married in Washington Carole told them "I'm going to Washington for a
visit, that's all. Mr. Markey is there and of course I will see him,
but there are no immediate plans to announce." Soon after they parted as friends.
Carole and director Hal Roach Jr. (son of producer Hal Roach) went out for a few weeks during the filming of One Million B.C. in the Fall of 1939. She left him for his friend Pat DicCicco.
Carole started dating producer Pat DiCicco (right with Gloria Vanderbilt) in December of 1939. She broke up with him two months later when he became violent.


Carole and art director Cedric Gibbons started dating in October of 1940. She described him as a perfect gentleman who taught her about interior decorating. After a month of dating she left him for Franchot Tone but they stayed friends.


Carole began a serious relationship with Franchot Tone in November of 1940. He took her to nightclubs and taught her about opera. She fell madly in love with him and wanted to get married. In a 1941 interview she said "I used to watch him when I first came to Hollywood, when he was still married to Joan Crawford and I'd think, what a lucky girl! I still say that any girl who gets Franchot will be a lucky girl." Although Franchot broke her heart when he ended the relationship in early 1941 they remained close friends.
Carole and movie legend Charlie Chaplin started dating in March of 1941. He gave her a 150-carat topaz bracelet in April but they broke up soon after. In 1947 she attended the premiere of Chaplin's film Monsieur Verdoux in England.
Carole had a fling with actor George Montgomery in during the Summer of 1941 when they made the musical Cadet Girl. They split up when filming was over.
Carole and actor Tony Martin dated for several months during the Fall of 1941. In September they attended the premiere of A Yank In The RAF together.
Carole went out on a few casual dates with Matty Fox, Vice-President of Universal Studios, in late 1941. They were seen dancing at the Mocambo nightclub in October.
Carole and her attorney Greg Bautzer went out together several times in 1942. He had represented her in her divorces from Irving Wheeler and Willis Hunt.


Carole dated publicist Alan Gordon for a few months in the 1942. They attended the premiere of Pride Of The Yankees together in August.
Carole dated millionaire Woolworth Donahue for a couple of months in late 1944
Carole had an an on-again off-again affair with entertainer George Jessel that lasted for years. He appeared in her 1944 film Four Jills In A Jeep and wanted her to star in his 1949 musical Dancing In The Dark.