Editing Bing Crosby (section)

===Romantic relationships===
Crosby was married twice. His first wife was actress and nightclub singer [[Dixie Lee]], to whom he was married from 1930 until she died of [[ovarian cancer]] in 1952. They had four sons: [[Gary Crosby (actor)|Gary]], twins [[Dennis Crosby|Dennis]] and [[Phillip Crosby|Phillip]], and [[Lindsay Crosby|Lindsay]]. ''[[Smash-Up: The Story of a Woman]]'' (1947) was rumored to be based on Dixie's life. The Crosby family lived at 10500 Camarillo Street in North Hollywood for more than five years.<ref>1940 US Census via Ancestry.com</ref>

After his wife died, Crosby had relationships with model [[Pat Sheehan (model)|Pat Sheehan]], who married his son Dennis in 1958, and actresses [[Inger Stevens]] and [[Grace Kelly]]. Crosby married actress [[Kathryn Crosby|Kathryn Grant]], who converted to Catholicism, in 1957.<ref>{{cite book |url={{Google books |LongDwAAQBAJ |page=41 |plainurl=yes}} |title=Top Models |first=Samuel |last=Claesson|publisher=Sequoia Press |year=2023 |page=24 |isbn=9798889921806}}</ref> They had three children: [[Harry Crosby (businessman)|Harry Lillis III]], who played Bill in ''[[Friday the 13th (1980 film)|Friday the 13th]]'', [[Mary Crosby|Mary Frances]], best known for portraying [[Kristin Shepard]] on TV's ''[[Dallas (TV series)|Dallas]]'', and [[Nathaniel Crosby|Nathaniel]], the 1981 U.S. Amateur champion in golf.<ref>{{cite web |title=Nathaniel Crosby wins 1981 U.S. Amateur Championship |url=https://www.usga.org/content/usga/home-page/videos/2016/09/01/1981-u-s--amateur-vignette-mp4-5107990318001.html |website=USGA.com}}</ref>

Particularly during the late 1930s and the 1940s, Crosby's domestic life was dominated by his wife's excessive drinking. His efforts to cure her with the help of specialists failed. Tired of Dixie's drinking, Crosby even asked her for a divorce in January 1941. During the 1940s, he consistently had difficulties trying to stay away from home, while also trying to be there as much as possible for his children.<ref name=GiddinsOct2018>{{cite book|title=Bing Crosby: Swinging on a Star; the War Years, 1940-1946|first=Gary |last=Giddins|publisher=Little, Brown and Company|date=October 2018|isbn=978-0-316-88792-2}}</ref>

Crosby had one confirmed extramarital affair between 1945 and the late 1940s, while married to his first wife Dixie. Actress [[Patricia Neal]], who herself at the time was having an affair with the married [[Gary Cooper]], wrote in her 1988 autobiography ''As I Am'' about a cruise to England with actress [[Joan Caulfield]] in 1948:

{{Blockquote|She [Caulfield] was a lovely girl and we had some good talks. She, too, was in love with an older married man who was quite as famous as Gary [Cooper]. She confided to me that she desperately wanted to marry Bing Crosby. We were in the same boat in more ways than one, but I could not tell her so.<ref>{{Cite book |title=As I Am |first=Patricia |last=Neal |page=109 |publisher=Simon and Schuster |date=1988}}</ref>}}

In the 2018 Crosby biography ''Bing Crosby: Swinging on a Star; the War Years, 1940–1946'', there are excerpts from an original diary of two sisters, Violet and Mary Barsa, who, as young women, used to stalk Crosby in New York City in December 1945 and January 1946, and who detailed their observations in the diary. The document reveals that, during that time, Crosby was taking Caulfield out to dinner, visited theaters and opera houses with her, and  Caulfield and a person in her company entered the [[Waldorf Astoria New York|Waldorf Hotel]] where Crosby was staying. The document also clearly indicates that at their meetings a third person, in most instances, Caulfield's mother, was present. In 1954, Caulfield admitted to a relationship with a "top film star" who was a married man with children, who, in the end, chose his wife and children over her.<ref name="GiddinsOct2018" />

Caulfield's sister, Betty Caulfield, confirmed the romantic relationship between Caulfield and Crosby. Despite being a Catholic, Crosby was seriously considering divorce in order to marry Caulfield. Either in December 1945 or January 1946, Crosby approached Cardinal Francis Spellman with his difficulties with dealing with his wife's alcoholism, his love for Caulfield and his plan to file for divorce. According to Betty Caulfield, Spellman told Crosby: "Bing, you are Father O'Malley and under no circumstances can Father O'Malley get a divorce." Around the same time, Crosby talked to his mother about his intentions and she protested. Ultimately, Crosby chose to end the relationship and to stay with his wife. Crosby and Dixie reconciled, and he continued trying to help her overcome her alcohol issues.<ref name="GiddinsOct2018" />

[[File:Bing, Harry and Nathan Crosby (1975) 02.jpg|thumb|upright|Bing, [[Harry Crosby (businessman)|Harry]], and [[Nathaniel Crosby|Nathan Crosby]], 1975]]