On a taxi ride home after a photo shoot, Tsugumi recounts her meeting with a man to her best friend and model Meiko. She speaks gushingly about their immediate mutual attraction, a feeling of "magic", and her excitement over future dates. Meiko later heads to an office where she confronts her ex-boyfriend, Kazuaki, whom she gathered is the same person Tsugumi was referring to. She relates things Tsugumi told her, including that Kazuaki could not get over his ex-girlfriend, and suggests that their relationship could be rekindled. Following a heated argument, Kazuaki hugs Meiko before she runs away.
Three days later, Meiko and Tsugumi are at a cafe when Kazuaki walks past. Tsugumi beckons him inside and introduces him to Meiko. Meiko immediately reveals their past and demands that Kazuaki choose between them, leading Tsugumi to storm out and Kazuaki chasing after her. The sequence is revealed to be fantasy and instead, Meiko quickly excuses herself, leaving Kazuaki and Tsugumi to plan their date alone.
College student Sasaki prostrates himself before French professor Segawa, begging the latter not to fail him as it would derail his future as a news anchor, but Segawa remains stern and unsympathetic. Months later at his apartment, Sasaki and his friend-with-benefits, married mother Nao, learn from the news that Segawa has won the prestigious Akutagawa Prize for his new novel. Sasaki coerces Nao into honey trapping the professor in order to create a scandal.
Nao visits Segawa at his office, ostensibly to request an autograph, while the door stays open at Segawa's insistence. She reads aloud an erotic passage from the book and asks explicit questions, though Segawa remains unmoved, and the two end up having a heart-to-heart conversation. Nao confesses that she was recording the conversation, and Segawa requests that she send him the audio. She agrees on the condition that he masturbates to the recording once, to which he verbally agrees. Once home, Nao mistypes the address by accident, and the email ends up being sent to a university administrator. The ensuing scandal leads to Segawa's disgrace and resignation and Nao's divorce.
Years later, Nao runs into Sasaki on the bus. She now works as a proofreader, while him an editor despite his lack of interest in literature. Sasaki shows no remorse for the affair, and Nao grows increasingly annoyed by his presence. Sasaki announces that he is getting married. As Nao reaches her stop, she hands Sasaki her business card, kisses him on the lips, and steps off.
Digital technology has mostly been abandoned since 2019 when a virus struck, resulting in uncontrollable leaks of personal and confidential information. Natsuko attends her all-girls high school reunion, finding that she does not fit in nor remember her classmates' names. Later at the train station, she recognizes a classmate she was desperately hoping to meet again and is invited to her home. The two reminisce, but eventually realize that they have mistaken each other for former classmates.
An embarrassed Natsuko attempts to leave but the host, Aya, convinces her to stay. Natsuko reveals that the person she mistook Aya for was her first love and she never got over their breakup in college. Aya offers to play the role of her ex-girlfriend and helps Natsuko vent her unresolved feelings. As they return to the train station, Natsuko learns that Aya mistook her for a classmate she used to play the piano with and admired. Natsuko role-plays as the classmate in turn, which allows Aya to confess to her insecurities despite a seemingly perfect married life. As they eventually part, Aya runs back to Natsuko and tells her that she has finally remembered her old classmate's name, and the two share a passionate embrace.
Rotten Tomatoes reported that 99% of critics have given the film a positive review based on 108 reviews, with an average rating of 8.4/10. The site's critics consensus reads "Writer-director Ryūsuke Hamaguchi explores multiple facets of the human condition with Wheel of Fortune and Fantasy, all to delightfully affecting effect."
On Metacritic, the film has an assigned score of 86 out of 100, based on 19 critic reviews, denoting "universal acclaim".
Wheel of Fortune and Fantasy was ranked fifth on Cahiers du Cinéma's top 10 films of 2022 list.