Bing Crosby and Grace Kelly's Love Affair


There is so much Hollywood History that we discover from reading personal letters from the starts long after they pass, and that is just what happened when we recently learned that Bing Crosby once asked Grace Kelly to marry him.


After a day on the set of 1954's The Country Girl, Grace Kelly loved to write letters to her then-fiancé, Oleg Cassini.

Grace and Oleg
Well, recently those letters, which were part of an auction of Oleg Cassini's estate, gave new insight into their relationship and Oleg's jealousy over her co-star Bing Crosby who at the time was dating his future wife Kathryn.


Bing, then 51, reportedly fell hard for Grace, 25, and proposed marriage, but in her letters, Grace sought to set Oleg's mind at ease.

Grace and Oleg
“I told you he said that he was in love with me - but there are many people that he feels that way about. Bing would never try to do anything about it - unless he thought I wanted it that way," she wrote.  “I have very few friends here - please don't ask me to give up their friendships."

Bing and Kathryn
The affair between Bing and Grace apparently continued even after Bing had proposed to Kathryn. Bing postponed his wedding to Kathryn that was set for Sept. 10, 1955, apparently because of Grace. Later that year, according to Kathryn, Bing apologized to Kathryn for his fling with the future princess.


Obviously, Grace never married Bing and she would ultimately call off her engagement to Oleg when she met Monaco's Prince Rainier in 1955.


Ah, what could have been. We ❤️ that someone who understood the importance of these letters set the record straight. Without it, Hollywood History might just become...history. xoxoxo


Bing Crosby and Grace Kelly's Love Affair Bing Crosby and Grace Kelly's Love Affair Reviewed by #IheartHollywood on July 08, 2019 Rating: 5

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