An old roué arrives in Hades to review his life with Satan, who will rule on his eligibility to enter the Underworld.

Upon the death of seventy-year-old Henry Van Cleve, a member of New York's social elite, he resigns himself to being sent to Hell and goes there directly. When he arrives, however, he is greeted by His Excellency, a well-dressed gentleman who demands to know what crimes Henry has committed that would justify his internment in Hell. Replying that the best way to relate the story of his life is to describe the women in it, Henry begins his tale: When he was born in 1872, Henry's mother Bertha and grandmother spoiled him constantly, and as he grew, he quickly began to notice the opposite sex. One day, young Henry shows little Mary a beetle, and as she sweetly persuades him to give her another beetle, Henry realizes, "If you want to win a girl, you have to have lots of beetles." The wealthy Van Cleve family, headed by Henry's indulgent father Randolph and his high-spirited grandfather, provide Henry with every luxury, including a maid to tutor him in French when he is fourteen years old. The lovely "Mademoiselle" is soon tutoring Henry in the ways of champagne and romance, until the morning of his fifteenth birthday, when his aghast parents find their son too hung-over to celebrate. Grandfather chuckles and whisks Mademoiselle out of the house before Randolph and Bertha can punish her. Henry's life as a happy-go-lucky drinker and skirt-chaser continues until his twenty-sixth birthday. That morning, Henry confesses to his mother that he has met the girl of his dreams and would gladly marry her, if only he knew her name. In the evening, Henry attends the dinner party celebrating the engagement of his stuffy, proper cousin Albert and his beautiful fiancée, Martha Strabel. Henry is overwhelmed by the sight of Martha, for she is the girl he fell in love with the previous day during a chance meeting at a bookstore. Henry presses his suit, and Martha, who is marrying Albert only to escape the Kansas home of her rich meatpacker parents, admits that she returns Henry's love. The couple elope that night, and Grandfather finances their honeymoon when the horrified Strabels disown Martha. Ten years later, on the day before Martha and Henry's anniversary, which is also Henry's thirty-sixth birthday, Henry is having breakfast with their son Jack when he receives a telegram from Martha, announcing that she has left him. Henry follows Martha to the Strabels' home in Kansas, where her parents have reluctantly reconciled with her. Albert, who met Martha on her train journey, tells her that he still loves her, although Martha barely listens to his declarations. Upon Henry's arrival, Martha reveals that she is aware of Henry's continued philandering, but his charm and Grandfather's determination convince her to forgive her errant husband and the couple "elope" again. Henry and Martha settle down happily as the years pass, until Henry grows worried about Jack's attachment to a chorus girl named Peggy Nash. Henry visits Peggy, who accepts his offer of $25,000 to leave Jack alone. Jack, who has been spoiled just as Henry was, has already tired of Peggy, however, and announces that he has a new girl friend. That night, Martha tells Henry that she likes the look of him now that he is fifty, for his slight potbelly means that he is no longer a Casanova. Later, at a party celebrating the couple's silver anniversary, Henry learns that Martha is ill, and they dance their last dance together. By the time he turns sixty, widower Henry has returned to his fun-loving ways. Jack, who has settled down and become a responsible businessman, despairs that his father stays out late every night, but a reminder of Martha prompts Henry to rescind his request for a young, female reading companion. Ten years later, on Henry's seventieth birthday, a visiting doctor warns Jack and his wife to watch the ailing old man's diet. In his bedroom, Henry wakes up from a dream about dancing with a beautiful blonde woman in a sea of whiskey and soda, then dies while the night nurse, a beautiful blonde, takes his temperature. Having completed his story, Henry is told by His Excellency that they do not cater to "his class of people" in Hell, and that he should apply elsewhere. Henry protests that he will not be admitted, but His Excellency assures him that someone special is waiting for him, and that she will be happy to plead his case.