Act One

Max, the story's narrator, appears. He begins to describe a romantic world of time gone by ("In Vienna"). Max introduces his friend, Anatol, who worries aloud that his love, Cora, is seeing someone else. He wants to call the relationship off, which seems easy enough during the day, but at night he cannot seem to resist her. Thinking himself silly, Max assures him that he is just a romantic ("I Love To Be In Love").

Anatol plots with Max to utilize some recently acquired lessons in hypnosis to get Cora to admit to her faithlessness. Cora, an older, self assured woman, whom Anatol compares to a tiger, agrees to play this game. Convincing her that the hypnosis is merely a homework assignment, Anatol begins to put her in a trance ("The Hypnotism Song"). Max and Anatol ask her a few questions to be sure she is hypnotized, then debate how to properly frame the question they've been dying to ask. Anatol continuously rejects all of Max's suggestions, which leads Max to believe he is simply afraid to know the truth. Anatol asks Max to leave so he can find out alone, but instead decides to wake Cora up without asking ("I Love To Be In Love [Reprise]").

Later, in Sacher's restaurant, there is great fun and entertainment when Annie and Fritz, the performers of the evening, sing "The Music of Bavaria." Meanwhile, upstairs, Anatol is in a private dining room preparing three waiters for the rough night ahead ("Finishing an Affair"). He confesses to Max that he has been seeing another woman and must end his relationship with the first, whom he now finds 'boring.'

The young woman arrives and it turns out to be Annie, the entertainer from downstairs. She is young and a bit dim, but finds great pleasure in eating. Amid ravenous bites, she explains that she is going to leave Anatol for another man. While Max chokes back tears of merriment at this turn of events, Anatol becomes indignant that Annie has decided to leave him before he can leave her. She explains to Anatol that because her new man is poor, she knows she will be leaving behind a life of rich decadence, especially bemoaning the loss of her beloved oysters on a nightly basis ("The Oyster Waltz"). Infuriated, Anatol tells Annie in great detail that he too has been deceiving her with another woman. Angry over how inconsiderate Anatol has been about his affair, she leaves in a huff.

Some time has passed, now in the streets at winter time; peddlers are selling Christmas gifts ("Come Buy a Trinket"). We see Gabrielle, a beautiful young woman of obvious wealth and breeding, carrying gift packages and looking for a cab. Anatol appears and tries to help her with them, and it soon becomes clear they have some history, although she is married and has children. She offers to help him find a gift and he reminds her that she could have stayed with him rather than marrying a man she didn't love. He explains to Gabrielle that he and his new woman live in a world far removed from one of wealth and social status, where they share a simple love ("There's A Room").

Gabrielle, clearly saddened but touched by his story, takes a bouquet of flowers she has been carrying and insists Anatol give them to his new love. She asks that he deliver a message with the flowers, where she clearly laments her decision not to stay with Anatol. She departs and he sadly confesses to a passing peddler that he has no room and no special place to go. He gives the bouquet to the peddler, followed by Max, who comes in and purchases them.

Act Two

Max appears and reveals that it is the morning of Anatol's wedding. Inside his apartment, we find a gloomy and inebriated Anatol. Max arrives, hoping to get some help with what color flowers to buy his bridesmaid wedding partner...only to find another woman in Anatol's bedroom. To Max's shock, Anatol explains that at a party the previous evening, there was a chill moment between Anatol and his fiancé when they said goodnight. Later that night, alone, Anatol wandered into a ball at the Redoute ("Anatol's Last Night"). Once there, he encounters Illona, a former lover. He had previously told her he was going out of town in order to avoid her. They spend the night together, however, and Anatol has a lovely time. Illona is now adamant that they never part again.

At that moment, Illona enters from the bedroom wearing her clothes from the night before. Max and Anatol try to distract Illona, an actress, by asking what her favorite scene in her new play is. She shares that it's the one in which she kills her lover with a letter opener ("Love Conquers All"). Illona declares that she and Anatol will spend the day drinking coffee and cuddling as they listen to the rain.

Max manages to escape to buy the bridesmaid's bouquet, but Illona refuses to let Anatol out of her sight ("Listen to the Rain"). Anatol insists that he must attend the wedding, but promises to meet her right afterward. While he is dressing, Illona begins to question Anatol's whereabouts. From his evasive answers, she suspects he has tried to get rid of her, so she vows never to let him leave her again. Illona goes crazy with fury and begins tearing up anything within reach. Max returns with his bridesmaid's bouquet, which Illona tears up as well. Anatol is informed that his carriage is ready, so Max urges him to leave while he stays behind to try and console Illona. Anatol goes and Illona is determined to follow and destroy the wedding. Max convinces her to leave it be, telling her that it is only a matter of time until Anatol comes back to her. Illona takes his advice and decides when that time comes she will make him suffer and beg.

With Illona gone, we see the passage of time, as Max remarks upon unstoppable changes ("Seasons Come, Seasons Go").

Time shifts forward. Anatol, now 52 years old, is reuniting with Max in an old cafe after many years apart. Anatol tells Max he needs him to hear his heart's last will and testament by renouncing love. He tells Max a story of how he recently spied a beautiful young singer, Annette, walking with her young poet lover, Flieder. Their eyes met and Anatol knew that Annette yearned for him. He tells Max he is too old, however, he will not bother or envy the young ("It's For The Young").

At that moment, the two hear noise in the distance. They realize it is the aging dandy Baron Diebel and his entourage from the Redoute coming in their direction. The Baron invites Anatol and Max to join them at the inn, as they were once the greatest lovers in Vienna. He tries to tempt Anatol with the beautiful young singer, Annette, that he has brought with him. The Baron continues to prod him and when Anatol refuses, slightly disgusted, the Baron defends himself by stating that he still is a moral man ("Ménage A Trois").

Max is convinced, and he and the Baron head to the inn. Moments later, the young Annette appears from the inn and tries to persuade Anatol to join the party. She confides in Anatol that her lover, Flieder, only wants to be alone with her and talk, while at times she would rather go to parties. She enchants Anatol into a conversation and once he describes a place in the forest where lovers can go to be alone, she tries to convince him to take her there and make love ("There's A Flower I Wear").

Suddenly, Flieder enters looking for Annette. Anatol gives Annette over to Flieder, and she begins to lead him to the forest instead. When Flieder is feeling jealous of Anatol, Annette assures him that he is just an old man. As the young couple departs, Annette flings a primrose at Anatol's feet, which he picks up and sticks in his lapel. As Anatol leaves, we see the various members of his life celebrating this game of love ("Game of Love").