- Won't you change partners? And then
You may never want to change partners again.—"Change Partners" (song from Carefree) by Irving Berlin
After Amanda Cooper (Rogers) breaks off her engagement to Stephen Arden (Bellamy) for the third time, he asks psychiatrist Tony Flagg (Astaire) to analyze her. Tony meets with Amanda several times, but something goes wrong with each appointment, and he makes no progress in finding the root of her Commitment Issues. Meanwhile, Amanda falls in love with Tony. When she tries to tell Stephen about it, he misunderstands and thinks she is finally ready to marry him. He excitedly announces their upcoming wedding just before Amanda confesses to Tony that she's fallen for him.
Convinced that she is merely confusing respect for a doctor with love, Tony hypnotizes Amanda into believing that she hates him and loves Stephen. Midway through the session, he realizes that he's making a mistake—not only does she truly love him, but he loves her too. However, before he can undo the suggestion, Amanda escapes from his office. Stephen is delighted with her newfound devotion to him even after he finds out the reason for it, and he convinces a judge to issue a restraining order preventing Tony from seeing Amanda. Tony must race against time to reverse Amanda's hypnosis-induced change of heart before she marries Stephen.
No connection to the webcomic of the same title.
Carefree provides examples of the following tropes:
- Big Damn Kiss: In the context of the Astaire-Rogers series, Amanda and Tony's dream kiss is this. Astaire jokingly called it "the kiss of the century." They had managed to make seven previous Romantic Comedy films without a full-on, mutual, romantic kiss onscreen. In Carefree, not only do they finally have that kiss, but it's in Slow Motion too.
- Brainwashed and Crazy: When Tony hypnotizes Amanda into hating him, he gives her a suggestion that "men like him should be shot down like dogs." Later, at the country club, she attempts to shoot Tony with a skeet-shooting rifle. It's Played for Laughs.
- Brief Accent Imitation: The Scottish golf pro comments that Tony is getting terrific length with his drives. Tony imitates his accent as he replies, "Thank you, Mr. MacPherson. You're verra, verra encouragin'." Then he switches back to his normal voice and adds with a chuckle, "It's about time, Mac."
- Cannot Dream: Amanda claims that she doesn't dream, so Tony orders her to eat some bizarre foods in order to encourage dreaming: seafood cocktail with whipped cream, welsh rarebit, lobster with mayonnaise, strawberry shortcake, and cucumbers with buttermilk.
- Commitment Issues: Tony says Amanda has a "phobia" of marriage. (Since she has no reservations about committing to Tony later, it's more likely that she just realizes deep down that she doesn't really want to marry Stephen.)
- Dance of Romance: Amanda first realizes her attraction to Tony after she dreams about dancing with him; she confirms it by getting him to dance with her in real life.
- Dance Sensation: "The Yam."
- Derailing Love Interests: Any sympathy the audience may have had for Stephen will likely disappear once he gets a restraining order and tries to marry Amanda while she's brainwashed into thinking she loves him.
- Disposable Fiancé: Stephen, for Amanda. In fact, she was trying to "dispose" of him before the story began.
- Eating the Eye Candy: Amanda's aunt Cora (Luella Gear) is very appreciative of Tony's hunky assistant Connors (Jack Carson).
- Erotic Dream: A G-rated version. Amanda dreams of dancing with Tony through a fairytale landscape, ending with a Hollywood Kiss.
- Ethnic Menial Labor: Hattie, Amanda's maid (played by Hattie McDaniel).
- Fake Static: Connors provides some when pretending to be a long-distance call. He makes some of the noises with his mouth and then puts the earphone to the speaker to create feedback.
- Go Talk to the Distraction: At a country club dance on the night before the wedding, Tony arranges for Stephen to be called away for a phone call (actually made by Connors from the lobby phone booth) so that Tony can try to reverse his suggestions to Amanda. He outlines his plan in the lyrics of the song "Change Partners":"Ask him to sit this one out, and while you're alone,
I'll tell the waiter to tell him he's wanted on the telephone."
- Hollywood Law: Legal proceedings (or threats of them) exist to provide impetus or obstacles to the plot and bear very little reference to real-world practices. All legal matters seem to be handled on a personal basis, as Judge Travers is a friend of both Stephen and Amanda.
- Hollywood Psych: Similarly, the psychiatric material in the movie exists just to drive the plot. In particular, hypnosis does not work that way.
- Hospital Hottie: Connors.
- Hypno Fool: After Amanda leaves Tony's office under hypnosis, she goes to the country club, where she gets into some crazy antics when she gets hold of Stephen's skeet-shooting rifle.
- Intoxication Ensues: Under the influence of a drug that lowers her inhibitions, Amanda breaks a large pane of sheet glass, kicks a policeman, and merrily insults the sponsor of her radio show. (A variation on the regular trope, as the drug is administered with her knowledge by a medical professional.)
- Involuntary Dance: Tony manages to get Amanda alone at a dance on the night before her wedding; he hypnotizes her, hoping to get a chance to reverse his earlier suggestions, and she dances with him in a trance.
- Japanese Politeness: Invoked by Connors when he makes a phone call to Stephen pretending to be Miss Satsuma Naguchi from the Honolulu Daily Bugle. He ends virtually every sentence with "please."
- Kissing Under the Influence: The first thing Amanda tries to do after being given a drug that will lower her inhibitions is kiss Tony.
- Larynx Dissonance: Connors pretending to be a female reporter on the telephone.
- Love Confession: Right after Stephen announces his and Amanda's upcoming wedding, Amanda tells Tony that she's fallen for him.
- Love Revelation Epiphany: When Tony hypnotizes Amanda, he plants the following suggestions in her mind: (1) she loves Stephen and wants to marry him; (2) Tony is a horrible monster, and men like him should be shot down like dogs; and (3) Tony does not love her. Her reaction to the last statement is so strong that Tony has to leave the room to think things over. After a short conversation with himself, he realizes that not only does she really love him, but he loves her too.
- Pimped-Out Dress: Amanda has one for each of her three dances, plus a Fairytale Wedding Dress in the final sequence.
- Recurring Dreams: Too embarrassed to tell Tony about her Erotic Dream and wanting an excuse to keep seeing him, Amanda invents a recurring nightmare, which she claims to have had since the age of eleven, involving Little Red Riding Hood and some evil squirrels.
- Rhetorical Request Blunder: Tony's suggestion to a hypnotized Amanda: "Dr. Flagg is a horrible monster. Men like him should be shot down like dogs."
- Running Gag: "Sit down, Joe!" from Aunt Cora to Judge Travers. (And finally, "Stand up, Joe!")
- Shipper on Deck: Aunt Cora ships Tony and Amanda.
- Short-Distance Phone Call: To get Stephen out of the way so that Tony can talk to Amanda, Connors fakes a phone call from Honolulu. He's actually in a phone booth in the country club lobby, while Stephen takes the call at the front desk.
- Slow Motion: Much of the dream dance ("I Used to Be Colorblind") is filmed this way, emphasizing the surreal feeling of the sequence.
- Tap on the Head: Stephen knocks Amanda unconscious when he tries to take a swing at Tony and accidentally hits her instead. Tony is able to use her unconscious state to reverse his hypnotic suggestions at last.
- The Man in the Mirror Talks Back: Tony has a conversation with his subconscious mind in this way, leading to his Love Epiphany.
- Triang Relations: Stephen loves Amanda, who loves Tony, who eventually loves Amanda.
- Wardrobe Wound: Judge Travers is quite upset when Amanda shoots the crown out of his best hat—"a real Tyrollean!"
- Why Waste a Wedding?: Everyone gathers for Amanda and Stephen's wedding, but it turns out to be Amanda and Tony's wedding instead.