A gambling son of a rich father returns to his beautiful girlfriend in England but falls in love with his sister’s friend, who is also from a wealthy family and breaks her engagement for him.
At an auction in the Kenya colony the property of Willie Hale (Ronald Coleman) is sold to low bidders by Willie himself so that people do not pay more than they are worth.
In London at the home of his father Lord Leland (Frederick Kerr) his daughter Susan Hale (Florence Britton) reads aloud an account of the auction. He is out of debt and has £100 for gambling. His father is upset that he wasted the house and furniture he gave him. Dorothy Hope (Loretta Young) comes in and notices his histrionics, and he goes out. Arthur (Crauford Kent) says he learned that Dorothy is nearly engaged to the Grand Duke Paul, and he goes out. Dorothy asks Susan about her brother Willie. She says he is eccentric, but she adores him.
Outside a station Willie hires a cab to take his luggage to his father’s house without him. Willie walks by a pet store and notices a friendly dog in the window. He carries on a conversation with the dog about buying him. He goes in and finds out the price is £15. Willie says he has only £20 left. He decides to offer ten, but the price is 15. As he is walking away, the dog barks. He turns, and the dog jumps up and down. Willie goes back and pays £15 for “George.” Carrying the dog, he sees a billboard about Mary Crayle starring in “Why Not Smile!” He takes a taxi to Liverpool.
Willie knocks, and a maid lets him enter a dressing-room. Mary Crayle (Myrna Loy) comes in and is so glad to see him she orders her understudy to go on for her.
At the breakfast table Leland is angry his son has not shown up, and he threatens to kick him out. Dorothy calls on them and says she will be officially engaged tonight. Leland implies that Willie is a ladies’ man. Dorothy has never met him. Willie comes in the front door with his dog, whom he hands to the butler. Willie enters the dining-room whistling and is questioned by his father where he was last night. Leland orders him to talk to him in his study; but Willie asks for some breakfast, and his father says he will wait for him. Willie meets Dorothy. Willie tells Susan he has only £2.
Willie enters the study and says he is glad his father is looking well. Willie sits down, and his father reprimands him for selling the house and furniture he gave him. His father says he has always been trouble. Willie implies he is not boring, and he declines to provoke him. Leland asks what he would do if he kicked him out. Willie says he will move on and up by his own efforts and he hopes with his father’s generosity. Leland agrees with that and gives him £100. Willie says it will be well spent. He advises his father to back Laguna in the Derby.
In the dining-room Willie invites Dorothy and Susan to go to the Derby with him. They go out and get in the car. The butler runs out with the dog, and Willie tells him to take good care of him because he is going to be a father.
At a carnival Willie and Dorothy go on the merry-go-round and down a slide together. Dorothy wins a prize. They find Susan waiting for them on a blanket for a picnic lunch. Susan offers to take his money and bet it for him. He tells her to put £50 for him on Laguna and ten for her and ten for Dorothy. Susan goes. Dorothy uses field glasses and sees Grand Duke Paul (Paul Cavanagh). Willie asks to see and uses the glasses. Paul is talking with Dorothy’s father, Mr. Hope (David Torrence). Susan comes back and says that Laguna is 50-1. They watch the race, and Laguna wins. They are happy. Willie hires a man to watch the lunch basket until next year.
Willie drives, and he sings with Susan and Dorothy in the front seat. Paul and Mr. Hope see them.
Paul calls on Dorothy and learns she went to the Derby with Susan and her brother. Her father comes in and forbids her to see Willie anymore. She says she has invited him to the party that evening.
Mary in a steam bath talks on the phone to Willie and says she will be waiting for him.
At the engagement party Willie is dancing with Dorothy while Paul disapproves. She asks him about Liverpool and says she knows all about her. Mr. Hope advises Paul to fetch Dorothy from the garden. She is asking Willie where he will go next time. Paul tells Dorothy he thinks her behavior is strange. He is rude to Willie, and Dorothy walks in to the party. She tells Paul to apologize to Willie. She admits that she likes Willie enormously even though he has not made love to her. She advises Paul to say she does not feel well and went to bed. She leaves the room, and in her bedroom she cries. Susan asks Willie what happened to Paul. Susan tells her brother that Dorothy likes him a lot. Willie asks Susan if he can leave her there, and she learns he is going to Liverpool.
Willie is talking with Mary, who asks why he seems so distant. She says she could be jealous.
Susan finds Willie in her room and says he made Dorothy free. Their father comes in with a message for Willie from Mr. Hope. Willie says he wants to see him at two o’clock. His father tells Willie he played his cards just right, but Willie says his father is bad.
In his home Mr. Hope tells Willie that his daughter broke off her engagement, and he blames Willie, who suggests she dislikes Paul. Mr. Hope calls him a worthless gambler. Mr. Hope threatens that if Dorothy marries him, he will not give her any money. Willie says he may go abroad again.
Willie asks the butler to take him to Dorothy. On the porch he tells her that he has only £1,500 and that he has been bad all his life. He says her father will cut her off, and he asks her to marry him. She says she will love it and agrees. He kisses her and offers to tell her about his life. She does not want to hear it, but then she asks about Liverpool. He says he liked her very much. She says she is jealous of her, and if he really loves her, he will swear never to see her again. Willie does so. They walk in the house and tell her father they are engaged. Willie leaves, and her father calls her a fool. He asks her how she will feel if he sees Mary Crayl again. Dorothy says if he does, she will not see him again.
At home Willie talks to his dog about how to tell Mary he cannot see her again. He starts to write a letter but cannot get it started.
Mr. Hope calls a detective agency and hires their best.
Willie decides to telephone Mary, who invites him to supper. He declines. He tries to tell her but says he will call her later. Willie asks the dog what he should do.
Willie finds Mary on the street outside her dressing-room. She pushes him into a cab, and a detective follows them. At her place she says she is frightened. Willie says he came to say goodbye.
Mr. Hope tells Dorothy that Willie is with Mary now. Dorothy does not believe him. He tells her to call him at her house. Mary asks Willie if he is getting married. She asks him to answer the phone. He hears it is Dorothy, who hears his voice and is crestfallen and hangs up. Mr. Hope tries to console Dorothy. She asks him to put £5,000 in her bank, and he agrees.
Willie is calling on Dorothy, who is cold to him. She says he is in love with Mary. She suggests he wanted her money, and she hands him a check. He asks what the £5,000 is for. She says she is grateful for the experience. He says he must be grateful and leaves.
Willie cashes the check at a bank and goes to his club. He offers a man £1,000. The man suggests the Grand Duke Paul could use it because he is very poor. Willie calls him a friend.
Mr. Hope tells Dorothy that Willie cashed his check at 10 and that Mary left for France. The butler brings in a note from Paul. She asks her father to read it. Paul thanks her for sending her £5,000, and he is going to Paris. Dorothy laughs and is happy. She hopes Willie did not leave with Mary. The detective is brought in and says Willie bought two tickets at a shipping office for New Zealand, one for a dog. Dorothy says she will beg him to take her with him.
Willie is packing, and his father asks why he is going to New Zealand. Dorothy comes in, and Susan gets her father to leave the room with her. Willie asks why she is there. Dorothy says she has forgiven him. He says he is angry because she insulted him by giving him £5,000. She asks what he will do in New Zealand. He says he will marry. She says her father would insist that he marry her before they sail. He says no and asks why he should. She says she is pretty and companionable. They argue and are reconciled. His father comes in laughing and says her father is downstairs and wants to lend them money to buy them a farm in England. His father is laughing because the next time he goes broke, it will be her father’s furniture he is selling and not his. Willie tells her to pay no attention to that wicked man, and they kiss.
This romantic comedy portrays a charming man who cares little for money. His joy of living wins over others, but jealousy causes problems to arise. Dorothy did not like Paul becoming jealous, but then she becomes jealous of Mary. Willie cannot help but explain to his former girlfriend why he will not be seeing her anymore and manages to win back Dorothy by giving her generous contribution to someone who needs it more than he.