Based on a play by Max Shulman and Robert Paul Smith, a bachelor with many girlfriends is visited by a school friend who is married. The bachelor meets a girl who wants to get married, and his friend dates one of his girlfriends.
Charlie Reader (Frank Sinatra) lays on a couch hugging and kissing Poppy Masters (Lola Albright). The doorbell rings, and Charlie lets Joe McCall (David Wayne) in. Joe says he came to stay with him, and Charlie gives him a martini. Joe says he left his wife Ethel. Poppy meets Joe and says goodbye to Charlie, leaving. Joe asks Charlie if there are more gorgeous girls. Joe says his wife asked him for separate vacations. Jessica Collins (Jarma Lewis) comes in and starts cleaning up. Charlie urges her to leave, and she kisses him and goes. Joe asks where the “tomatoes” come from. Charlie complains about how Joe edged him out and married Ethel. Another gal calls, and Charlie says it is because he is single. Charlie says he would trade with Joe, who tells him about what comes with it. Joe says he has not looked at another woman in eleven years. Charlie turns on television to see Sylvia Crewes (Celeste Holm) playing violin in an orchestra. Helen comes in and takes Charlie’s dog out for a walk.
Sylvia gets in an elevator with Mr. Loughran (Tom Helman). Sylvia comes in and sees Charlie in a bathrobe when she wants him in a tuxedo. She leaves and comes right back. She talks with Joe about his family. Charlie comes in dressed up and goes out with Sylvia. Joe opens the door for Helen and the dog. Joe invites her, but she says he is a married man and leaves.
At a theater Charlie, Mr. Sayers (Howard St. John), Joe, Eddie, and Sylvia watch auditions. Julie Gillis (Debbie Reynolds) introduces herself and then sings. Julie joins Charlie, Sylvia, and Joe at lunch. Julie says she thinks marriage is better than a career. They ask her about the man she wants, and she says she wants three children and a house in Scarsdale. Julie says goodbye and is escorted away by Charlie. Joe and Sylvia make fun of Julie. Charlie tells Julie he will have a contract for her, and he invites her to dinner. She asks why, and he says it is good for his digestion. She says it is not part of her plan because she feels no chemistry with him.
Charlie comes into the theater, and Mr. Sayers shows him Julie is there. She is refusing to sign a contract beyond March 12, which is her parents’ anniversary and her deadline. He asks her to dinner again, and she declines again. Charlie advises Mr. Sayers to sign her until March, and he will try to change her mind.
In the apartment Joe answers the phone and takes a message. Charlie comes in and reads his messages. Joe says Ethel called. Joe gets a call from Sayers and learns that Julie did not show up for rehearsal. Joe turns on the television. They see Julie asking a question about a model kitchen. Joe warns Charlie that she is a trap. Joe says Charlie has a date with Sylvia, but Charlie leaves.
Charlie sees Julie arguing with the manager of the model house. She asks Charlie to sit in a chair, and she is mesmerized. Joe meets Sylvia at NBC and says Charlie got a call. He offers to fill in, and she accepts him.
In the theater Julie sings “The Tender Trap” and dances. The director likes her, and she asks Charlie. He plays piano and sings the song to show her how it could be better. She suggests they go out together. Joe spends time with Sylvia.
Joe takes a call from Poppy, and then Charlie comes in. Charlie says Julie is coming, and Joe tells him she is too young. Charlie learns that Joe is going out with Sylvia again. Joe leaves, and Julie comes in, followed by Helen with the dog, coming in and going out. Julie asks who she is. Charlie says she is a professional dog-walker. Julie asks why she is so attractive. She complains that the evening is planned without consulting her. He asks what she wants to do. She does not know, and he makes suggestions. She says he knows more about how to treat a lady. He stops her from reading his messages.
Charlie and Julie dance, and he learns her parents are away from home. He takes her home and embraces her. She offers him a drink. They hug on the couch, and he turns out the light. She complains he is nibbling. She turns on the television, and they watch Esther Williams swimming with a man. She turns it off and shows him an art book. They see a couple next door necking. He kisses her, and she takes the messages out of his pocket. She asks him how many girls are in his life. He mentions two, and she asks about the four notes. He says there is no one but her. She demands an answer, and he says 496. She tells him he will call for her at her house and meet her parents and do what she wants. He asks why, and she says she loves him. She says he is selfish, arrogant, spoiled, and too old for her. She lectures him that he has to learn about women. She wants to marry him, and he asks who asked her. He asks her if this is an ultimatum. He advises her not to propose to a man until he shows some interest. He says he knows many girls he likes better. She tells him to get out, and he leaves.
Charlie comes in and tells Joe what she said. Helen comes in, and Charlie invites her to dinner. She says she decided to marry the owner of a poodle she met. Poppy comes in and gives Charlie a fish. He hopes she will go out to dinner with him, but she says she has a date. He tells her to get rid of him, but she says he will call her tomorrow. She admits Charlie is a stinker and leaves. Joe says Charlie is getting paid back by all the girls he neglected. Joe tells him he is a louse. Joe says Sylvia is coming to pick him up. Charlie tells Joe not to see her because he is married. Joe says he will if Charlie will marry her.
Mr. Loughran speaks to Sylvia at the elevator. Sylvia comes in, and Joe says he quarreled with Charlie over her. Joe asks her why she stands for it. She says women come to New York for a career, and pretty soon they are 33 without a man. She lists the type of men available to a woman of that age. Charlie comes in and calls Sylvia “darling.” He asks her to marry him, and she says she will. She cries, and Joe wishes him luck. Charlie says it was his idea. Charlie suggests they get drunk. Charlie wants to have a party and calls a couple. He calls Sol Steiner and asks him to bring others. Jessica comes in and learns that Sylvia is engaged to Charlie. She gives Sylvia the cheese, kisses Charlie, and leaves. Charlie sends Sylvia out with money to buy food. Charlie goes out to buy liquor and gets in a taxi with Julie. They embrace, and he says he needs reforming. He sees guests arriving, kisses her, and says he will call her in the morning. Guests carry Charlie on their shoulders.
The next day Joe with a can of tomato juice looks for an empty glass. Charlie in a robe staggers in. Joe thinks he got engaged to a woman and asks who she is. Under the sofabed he finds Sol Steiner (Joey Faye). Sol asks why Charlie let Sylvia go home. Sol takes a bottle and walks out. Julie comes in and says she has been calling for three hours. She asks what happened there. Sylvia comes in and hugs Charlie. She asks if they found a diamond earring. Julie asks the occasion for the party and says she and Charlie became engaged last night. Joe explains the party was for his engagement to Sylvia. Charlie admits it. Julie says he is a terrible man and leaves. Charlie goes after her. Joe tells Sylvia he stayed awake all night, and he says he loves her. He asks Sylvia to marry him, and he has to write Ethel a letter. Sylvia suggests he call Ethel, but the phone is disconnected. Sylvia says Joe loves Ethel, and he has the married man’s dream—a girl, not a wife. Sylvia says she likes him, but she does not love him. He thanks her. Charlie comes back in and says the taxi door hit his hands. Sylvia says her courtship was lacking. Charlie says he is an unhappy heal, and she is most wonderful. He says he fell in love with Julie. Sylvia hopes to meet a good man. Mr. Loughran returns the fish and says hello to Sylvia. She leaves, and Loughran asks if she plays on NBC. In the elevator he is going to invite her to dinner.
Joe is packing and tells Charlie he is going home. Charlie says he wants only Julie. Joe thanks Charlie and leaves.
A year later Charlie returns from a tour in Europe to attend the wedding of Sylvia and Mr. Loughran, and he comes in at the end. Sylvia throws her bouquet to him. Charlie sees Julie and tosses the bouquet to her. He asks her to marry him, and she asks why. He says he loves her. He will pick her up and take her to the license bureau. They kiss.
This comedy foreshadows the coming sexual revolution in which sex before marriage can be casual with different partners on different nights. A married man can have a fling and realize he loves his wife. His example helps persuade his friend that he may be happier with just one woman. Also attractive women who know what they want can usually find it.