Ginger Rogers - 1911; William Holden; 1918; Pat Crowley 1933
The story plays like Holden is Rogers boy toy - he's 7 years younger than Rogers. Pat Crowley is 15 years younger than Holden so actually she's his girl toy more than Holden is Rogers boy toy.
I too thought Holden was woefully miscast. Stanley is supposed to be a young aspiring playwright who works in the marketplace to make ends meet; still hopeful but not yet disillusioned by his lack of success. The way they kept referring to him as "the kid," the character should still be in his twenties. Holden was 35 in this but looked at least a decade older. He drank heavily, which prematurely aged him. Not only was he 15 years older than Pat Crowley, but he looked 25 years her senior. Ginger is the one who actually looked youthful, IMO.
Anyway, some of the scenes don't work because of Holden. For example, when Stanley keeps bringing fruits and vegetables to Bea's house because he gets an employee's discount, a young man could make that strange gesture come off endearing. But it just comes off creepy with seemingly middle-aged Holden. The script desperately calls for him to have an "Aww, shucks!" attitude, but Holden can't pull it off.
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Interesting comments, and to some extent, I agree. It seems ironic, doesn't it, that Paramount would have cast Holden in his film given the story is about a star trying to play younger-- when that is exactly what they made Holden do with his role.
But we don't tend to notice it right away, because the focus is on the women concealing their age. Not the men.