The short starts with a sky view of a city with lots of neon lights for various clubs and upbeat jazz music, but then switches to a tree penthouse in the park where Chip & Dale reside. Both scoff the city nightlife and, after closing the curtain, go to bed.
However, Chip fakes going to sleep to read a love note from Clarice, a female singer, who writes "See you tonight." Chip then waits for Dale to sleepwalk out of the penthouse before he jumps out of bed and takes off his nightshirt to reveal a tuxedo underneath. After a moment of checking himself in the mirror, he gets a top hat, cane, and a bouquet of flowers and heads off to see Clarice.
Meanwhile, Dale stops "sleepwalking" to ditch his nightsirt and cap for a tuxedo, top hat, cane, and bouquet. He, too, receives a note from Clarice, asking to "meet me tonight." Oblivious to the other, Chip & Dale head for the Acorn Club, where Clarice sings.
Chip arrives first, knocking on Clarice's dressing room door and moves to the side, ready to surprise her. However, Dale then arrives and knocks, on Chip's head. The two begin to argue until Clarice, who answered her door, gets their attention. The boys then try to sabotage the other's attempts to woo the female:
- Chip bumps Dale aside when both jump into view at Clarice's door.
- Dale uses scissors to crop Chip's bouquet, leaving only stems.
- Chip slips a hose into Dale's bouquet, which he sniffs just as water gushes out into Dale's face.
- Chip presents a box of candies to Clarice, but when she gives him the first piece, it turned out to be a mothball Dale slipped into the box.
A fistfight ensues, with Clarice laughing as she watches, until she's paged that she's on stage next and she abandons the two. When Chip & Dale realize she's gone, they quickly race each other to catch the beginning of her performance. Clarice, near the end of her song, takes a flower and throws it at the two, causing them to dance onto the stage to catch it until Chip runs into the piano, allowing Dale to get the flower.
Chip, while Clarice finishes her song, begins playing the piano, getting her attention. In retaliation, Dale grabs a nearby bass and the two have a musical showdown.
In the end, both receive a kiss from Clarice, who enjoyed their playing, and join her in one last quick song. Clarice ducks when both try for one more kiss and they end up kissing each other, ending with all three laughing.
Edits for Television
- When Chip checks himself in his vanity before he leaves his and Dale's penthouse, near the end a voice tells him "you gay dog, you," while he raises his one eyebrow several times. The line is removed entirely.
- The clip of Dale holding a box of moth balls while he laughs at Chip for eating one was removed, showing instead a clip of Clarice laughing before Chip and Dale break out into their fistfight. The clip was later returned, though the text on the box reading "moth balls" is removed via digital editing.
- When shown on an episode of House of Mouse, not only the "you gay dog, you" line is missing, yet the text on the box reading "moth balls" is removed via digital editing.
- Dessie Flynn - Dale (1st)
- Jimmy MacDonald - Chip (1st)
- Corey Burton - Dale (2nd)
- Tress MacNeille - Chip (2nd)
- Martha Tilton - Clarice
- Walt Disney Presents, episode #5.20: "The Adventures of Chip 'n' Dale"
- The New Mickey Mouse Club, March 11, 1977
- Good Morning, Mickey, episode #10
- The Magical World of Disney, episode #33.15: "Mickey's Happy Valentine Special"
- Donald's Quack Attack, episode #39
- The Ink and Paint Club, episode #1.48: "The Return of Chip 'N Dale"
- House of Mouse, episode #3.8: "Chip & Dale"
- Walt Disney's Classic Cartoon Favorites, Vol. 4: Starring Chip 'N' Dale
- Chip 'n' Dale Volume 1: Here Comes Trouble
- When Chip & Dale are seen walking along two separate paths to the Acorn Club, Dale is on the left and Chip is on the right with the camera showing them walking towards the viewer. When we see them each enter the club, shown in reverse, Dale should be first and Chip second. However, in the next shot, Chip arrives at Clarice's dressing room first, with Dale showing up later.
- Several human objects are used by the characters in the short in different ways: A large box of matches filled with straw for a bed with a stuffed tobacco pouch for a pillow, a compact mirror for a vanity, a smoker's pipe end for a flower pot, matches and string used for stairway railing, a tea cup and saucer used for a serving tray and lid, and a pencil and small box of matches with strings used for a flat bass.
- Chip and Dale's rivalry over Clarice would later inspire their similar rivalry for Gadget Hackwrench's affections in Chip 'n Dale Rescue Rangers. The gag with Chip and Dale accidentally kissing each other when they both try to kiss Clarice at the end was even reused for the ending of the episode "Gadget Goes Hawaiian."
- This is the only short in which both Chip and Dale are voiced by men instead of women.