Stephen Arden (Ralph Bellamy) is in a state of inebriation thanks to troubles with the woman he wishes to become his wife, Amanda Cooper (Ginger Rogers). He has asked for her hand in marriage, but she keeps turning him down, unsure of whether she really loves him or not, so Stephen has drunkenly turned up at the offices of his old friend, psychiatrist Tony Flagg (Fred Astaire), to see if he can help. Once he finally makes it up to see him, Tony and his assistant Connors (Jack Carson) try to walk his stupor off and they settle on a solution to his worries: Tony will psychoanalyse Amanda. However, they don't get off on the right foot...
If you thought the Astaire and Rogers plotlines were ridiculous before, then they had nothing on Carefree, a soufflé of cross purposes and ludicrous behaviour that represented their second to last film together of their original cycle until The Barkleys of Broadway at the end of the next decade. It was a disappointment compared to their past successes and is now almost forgotten, overshadowed by the likes of The Gay Divorcee and Top Hat which contained notably more dancing and musical numbers. That might have been the reason it failed, although what songs there were were still composed by Irving Berlin.
But those songs included the frivolous "The Yam", which may lead into the best dancing of the picture but also contains one of the flimsiest excuses for a new Terpsichorean craze ever, which naturally never caught on (a dance named after a vegetable? How glamorous!). This film marked somewhere near the beginning of Hollywood's obsession with all things psychiatric although here none of it is taken the slightest bit seriously until it jeopardises Tony and Amanda's happiness. It is unusual for having Rogers chase Astaire for a change, but even then it resolves into the traditional him pursuing her for the final act.
It starts on fairly familiar territory, with Astaire's fancy moves explained by a remark about how Tony wanted to be a dancer before he became a psychiatrist, and Amanda insulted by his chauvinism when she accidentally plays a recording of his notes which describes her unflatterningly as a dizzy dame without even seeing her. However, these antagonisms are resolved after a spot of golf (Astaire's routine with the golf club is probably the most famous part of this - he even performs a Highland fling) and a bicycle ride, and soon Amanda is Tony's willing patient, and growing quite taken with her new doctor.
As Amanda's boyfriend is played by Ralph Bellamy there's little surprise about who gets the girl, but the path of true love never did run smooth, so there's a wealth of screwball comedy to plough through. That genre was never the most sensible, yet here they almost abuse their privilege with such sequences as Amanda eating a four course meal of rich food to make her dreams interesting so Tony can analyse them - it ends with a dance in slow motion between her and Tony that she has to make up a story about to cover up her real feelings. It gets even more preposterous when Rogers has to go on the rampage after being dazed, more than one rampage actually as she also brandishes a double-barrelled shotgun to scare the crowd at a clay pigeon shoot: ah, the magic of hypnosis! Add into this the one great song, "Change Partners" and you have a film constantly going overboard but managing to hold back in the musical numbers.