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One Sunday afternoon in the first decade of the twentieth century, small-town dentist Lucius "Biff" Grimes is seized with the thought of revenge when his former rival, Hugo Barnstead, arrives in town and comes to his office with an aching tooth.  While his friend, Snappy Downer, stands by and Hugo lies unconscious from nitrous oxide, Biff reminisces about the night years ago when he and Virginia Brush met in Avery's Park.

Although Virginia's shy friend, Amy Lind, has been infatuated with Biff since high school, he has always wanted to meet Virginia and gets his chance when she drops her handkerchief.  Full of himself, Biff is unaware that Virginia is really interested in his friend Hugo, as the four cavort at the park.

Sometime later, Biff slugs a fellow in a pool hall who teases him about Virginia, and his new straw hat, which he bought to impress Virginia, is stomped on in the subsequent brawl.  At a picnic in Schneider's Park, Biff learns which basket that is about to be auctioned was prepared by Virginia, and he wins it in the bidding, which allows him the opportunity to eat with her.  Although Virginia is upset to be with Biff, having arranged for Hugo to choose her basket, Biff is oblivious to her true feelings about him.  Another fight breaks out in the park, and when it is over, Biff sees Virginia with Hugo.

When Virginia elopes with Hugo, as Biff waits for her to keep a date in the park, a crowd of guys decide to go give Biff "the horse laugh."  Amy gets to Biff first, and when the others arrive and taunt him, she says, to shut them up, that Biff is engaged to her.  Biff and Amy walk off to a lake, where, although he is disheartened that Virginia married Hugo, he asks Amy to marry him.

Two years later, Biff learns that Hugo has returned to town with Virginia, sent by his uncle to take charge of the carriage factory, where Biff works.  Biff excitedly practices saying hello to Virginia and forgets that it is his and Amy's anniversary.  Amy cries when she realizes that he has forgotten, and as Biff embraces her, Hugo and Virginia come in and invite them to an anniversary dinner in their hotel suite.  Amy is upset because she has worked preparing her own dinner all day and is wearing a new dress, which no one has noticed.  Hugo puts on airs and denigrates Biff's ambition to continue to study dentistry at night and instead offers him a "better" position at the factory as a company spy, reporting on the men who should be fired.  Biff is insulted, and afterward tells Amy that she looks as nice as Virginia.

Hugo soon fires Biff for incompetency, and when Biff returns home, he finds that Amy has invited her mother to live with them.  Without relating that he has been fired, Biff returns to Hugo's office and vows to work harder in his old job.  Hugo gives him the job back, but then says he wants the names of the men he should get rid of.  Biff calls Hugo a "weasel" and as a guard struggles to put him out, the guard's gun goes off and he falls, having been shot in the leg.  Hugo blames Biff and he is sentenced to two years in the state penitentiary.  Biff vows to Snappy that he will revenge himself on Hugo when he gets out.  Upon his release, Biff vows to make it up to Amy, who has remained devoted to him and worked hard during his term in prison.  He suggests that they go someplace else to start over, and she says she will go anywhere with him.

Back in the office, Biff turns down the oxygen on Hugo and increases the flow of nitrous oxide.  Virginia then arrives with a painted face and an outlandish hat.  Biff immediately knows from her crass manner that he married the right woman, and he quickly turns off the nitrous oxide and puts the oxygen on.  Relieved that Hugo is alive, Biff pulls his tooth.  Virginia's crude attempt to flirt is ridiculed by Biff and Snappy after she and Hugo leave, and the sound of their uproarious laughter brings Amy to the office, where she accuses the two of drinking.  Biff then tells his wife that she's very sweet and beautiful, and that he loves her, and after she returns the sentiment, he carries her out, and they go for a long walk in the summertime air.