Even with Ruby Keeler's tinny voice and the fact she doesn't dance a step, Flirtation Walk is an utterly charming musical from the Thirties with Dick Powell at the height of his lyric tenor period.
West Point's image has done very well by Hollywood. The West Point Story and The Long Gray Line are the other two big films about the U.S. Military Academy on the Hudson. But this was the first film of a grand tradition.
Dick Powell is an army private stationed out in Hawaii who's assigned by his sergeant Pat O'Brien to be a driver for Ruby Keeler, daughter of General Henry O'Neill. She's got a boyfriend in her Dad's aide John Eldredge. But on a moonlight night in Hawaii, the old boy/girl thing happens.
Powell receives a rude awakening the next day when he's made to realize the difference in class between officers and enlisted men. Something like the rude awakening John Agar got in Fort Apache when he was courting Shirley Temple even though he was an officer, albeit a newly minted one from an enlisted man's family. So Powell decided he's going to become an officer and sets about applying for West Point.
The next half of the film is set in West Point and in Powell's final year, Henry O'Neill becomes the Academy Superintendent bring of course Keeler and Eldredge come with him. Here we have the same plot device that was later used in The West Point Story, breaking precedent in having a woman in the Hundred Nights show for the graduating class. Who do you think the woman that the cadets want?
Allie Wrubel and Mort Dixon wrote two nice numbers that are used in the musical show, Mr. and Mrs. Is the Name and Flirtation Walk. Powell sings them well although he didn't need Ruby's thin voice doing the reprise. During the Hawaiian portion of the film Powell sang Aloha Oe. Why Ruby wasn't given any dance numbers is beyond me since that was her strength as a performer.
I should also mention Ross Alexander, who came to a tragic early end three years later, as Powell's roommate at the Point. He was a funny guy and had a nice career going in playing best friends to the hero in film. A sad waste.
I think you'll like the characters created and directed by Frank Borzage in this very charming film.