Carefree 1938

Stephen Arden Ralph Bellamy enlists his best friend, psychiatrist Dr. Tony Flagg Fred Astaire, to psychoanalyze his fiancée, Amanda Cooper Ginger Rogers, a radio singer who has balked at the engagement for the third time. Tony reluctantly agrees, and before meeting Amanda, he records his opinion of her into his dictaphone, describing her as a

“dizzy, silly, maladjusted female who can’t make up her mind”

Amanda accidentally overhears the recording, upsetting her. When Tony returns, he tries to explain the principle of psychoanalysis to Amanda, but she rebuffs him and leaves, much to his confusion.

The next day, Stephen invites Tony to a country club so he can continue his analysis of Amanda. Eventually, she admits to Tony that she was angry after overhearing the recording, and he apologizes. To determine the root cause of Amanda’s fear of commitment, Tony intends to probe her subconscious mind and interpret her dreams. Since Amanda maintains that she does not dream, Tony orders her to have a meal of bizarre food combinations over dinner in order to induce dreams. That night, Amanda dreams of dancing with Tony, culminating in a kiss.

The next day in Tony’s office, Amanda is too embarrassed to tell him about her dream and instead invents a convoluted recurring nightmare, in which she is both Little Red Riding Hood and the Big Bad Wolf and is then chased by vicious squirrels. Convinced that he has found

the most beautiful case of complex maladjustment

, Tony gives Amanda an anesthetic to lower her inhibitions. After Tony leaves the examination room, Stephen bursts in and reminds Amanda that she is due to perform on a radio show very shortly, unaware that she is under the influence of the anesthetic. The drugged Amanda breaks a pane of glass, insults the sponsor of the radio show, and kicks a policeman.

That evening, Amanda confides in Aunt Cora Luella Gear that she loves Tony, before the women are joined by Tony, Stephen, and Judge Travers Clarence Kolb for dinner. When Amanda tries to break up with Stephen, he misinterprets her words and assumes that she has finally agreed to marry him. Stephen excitedly announces his engagement to the others, thanking Tony for his help. Amanda then asks Tony for a dance, whereupon she confesses her love for him.

The next day, Tony hypnotizes Amanda into thinking that she wants to marry Stephen and that men like Tony

should be shot down like dogs

. Tony soon realizes that he is in love with Amanda, only to find that she has left his office.

Still hypnotized, Amanda finds Stephen shooting skeet with Judge Travers at the country club. When Tony arrives, Amanda grabs a shotgun and starts shooting at him until he snaps her out of her trance. After Tony explains the situation to Stephen, including his newfound love for Amanda, Stephen accuses Tony of trying to steal his fiancée, and convinces Judge Travers to issue a restraining order that prevents Tony from seeing Amanda. Crashing Amanda and Stephen’s engagement party, Tony schemes with his assistant Connors to find Amanda alone, but his attempts to re-hypnotize her are foiled by Stephen.

On Amanda and Stephen’s wedding day, Tony and Connors sneak in with Aunt Cora’s help. Tony intends to knock Amanda unconscious with a punch so he can hypnotize her, but cannot bring himself to do it when he comes face-to-face with her. Stephen barges in and aims a punch at Tony but accidentally knocks out Amanda instead. While Aunt Cora and Connors restrain Stephen, Tony tells an unconscious Amanda that he loves her. Amanda, sporting a black eye, walks down the aisle with Tony.