It starts out with one of the all-time Life Imitates Art moments in film: a naval and air attack on Pearl Harbor, Hawaii. But it's just a drill! (Remember, 1934. They probably should have practiced more.) Richard Dorsey (Dick Powell) is a private in the Army stationed on Oahu, with a contentious but generally friendly relationship with his sergeant, "Scrapper" (Pat O'Brien). The routine of Army life in Hawaii is disturbed by the arrival of General Fitts and, more importantly, his lovely daughter Kit (Ruby Keeler). Gen. Fitts seems to think his daughter a match for a junior officer, Lt. Biddle, but she is drawn to Pvt. Dorsey.
Dick gets assigned to be Kit's driver. Instead of going to the Army ball she's supposed to attend, Kit prevails on Dick to take her on a moonlit drive around Oahu, which involves a luau, which then involves Dick and Kit cuddling on the beach, which then ends with the two of them being caught by Fitts and Biddle. Dick narrowly avoids a court-martial, but when Lt. Biddle sneers that "an officer and a gentleman" would not have gotten caught in such a position, Dick is affronted. He decides to apply to West Point and become an officer. Dick is accepted at West Point and does very well there—until Gen. Fitts arrives at West Point to be commandant, with Biddle and Kit in tow.
- Asian Hooker Stereotype: Hinted at, and possibly an Ur-Example or Unbuilt Trope. One scene has Scrapper's buddy Sleepy in China, with two Chinese girls sitting on his lap, giggling and feeding him by hand. The trope is promptly subverted when Sleepy has to hurriedly leave, and the girls/hookers reveal that they stole his wallet and watch.
- Busby Berkeley Number: The native Hawaiian luau turns into one of these.
- Drill Sergeant Nasty: Not Scrapper, but the upperclassman at West Point who screws with Dick the plebe For the Evulz.
- Gentlemen Rankers: Kit recognizes the name "Dorsey" and discovers that Dick is actually from a rich Old Money family. Why he's serving as a private is not explained, but it does ease Dick's transition when he decides to become an officer.
- Head-Turning Beauty: The cadets at West Point are practically rioting after Kit shows up on campus. When Dick refuses to write her into the show the cadets are putting on, they remove him as director. All of them leap up like jack-in-the-boxes when she shows up for rehearsal. No one pays attention as Dick is giving them directions because everyone is gawking at Kit.
- Hula and Luaus: What do Kit and Dick find as they're aimlessly driving along the coast of Oahu? They find a luau, of course. A luau that features several dozen native Hawaiians, singing and dancing in perfect harmony with careful choreography.
- Manly Tears: Scrapper cries at Dick's West Point graduation ceremony.
- Meet Cute: Dick is picking up Kit's luggage at the dock. One suitcase falls to the ground and spills open, revealing all of her flimsy lingerie.
- The Musical: Six original songs, as well as some Hawaiian music, including "Aloha 'Oe" as performed by native Hawaiians and then by Dick Powell.
- Only Known by Their Nickname: It's either this, or Scrapper had parents cruel enough to name him "Scrapper".
- Right Behind Me: After the artillery exercise that's Dick's part of the Pearl Harbor drill, another soldier asks where the target report is. Dick says "Oh, you know the Scrapper, probably has to count it up on his fingers. There's the slowest thinking guy I..." This is where he's interrupted by Scrapper, who's right behind him. Scrapper punches him in the face.
- Romantic False Lead: Is there any chance that Kit will wind up with starchy Lt. Biddle? No, no there is not.
- Sexy Backless Outfit: Kit wears one for the dance that she doesn't go to, skipping out for a drive with Dick instead.
- Shout-Out to Shakespeare: Kit insists that Dick drive her off-post and not to the dance, saying "Drive on, Macduff!"Scrapper: Macduff? He gave her the wrong name!
- Title Drop: Dick takes Kit along "Flirtation Walk", which as it turns out is a Real Life walking trail on the West Point grounds where cadets traditionally take their sweethearts.