Philadelphia, Pennsylvania weatherman Taylor Worth meets his friends, Eric, Gus, and Ned Braudy, and Ned’s three-year-old daughter at a racetrack clubhouse. Before the can sit down, Taylor’s girl friend, Lizbette, comes over to ask why Taylor asked her roommate on a date. Taylor calms Lizbette, then breaks up with her using the “you’re too good for me” strategy. While this is unfolds, Ned states his professional opinion as a psychologist, which is that Taylor suffers from “commitment phobia,” and can only be cured by finding unrequited love. Eric believes this to be impossible, however, as no woman can reject Taylor. When Taylor returns to the table, Ned bets his wife’s Pablo Picasso painting against Taylor’s fishing lodge that Taylor cannot get three women of Ned’s choosing to accept a marriage proposal. As Taylor takes the bet, cheerleader Erin Cooper enters accompanied by Tarry Childs, a tackle for the Philadelphia Eagles football team. When Ned informs Taylor that Erin is his first test, Taylor exclaims all beautiful women are lonely and he just needs an opening to talk to her. Taylor sends Ned’s daughter to talk to Erin, and when Taylor retrieves the little girl, he asks Erin out. Ned goes home and overhears his wife, Claire, talking to her friend, famous pianist Veronica Briskow, about hating men who show off their wealth and are vain about their looks. The next day at the golf course, Ned presents a contract outlining the wager, listing Erin, Veronica, and Eleanor Larimore, a member of his country club, as the targets. Taylor protests Eleanor is married, but Ned explains she is unhappily married. Taylor signs, only to learn that Ned slipped in a three-month deadline and a clause stating all proposals must be videotaped to be valid. Taylor decides that to win Erin he must put off seducing her. This proves troublesome on their first date when she demonstrates how to tackle and lands on him. Restraining himself, Taylor escorts Erin home. Later that night, Veronica comes to the television studio to watch Taylor “read the weather,” and turns down his offer for dinner. The next day, Taylor follows Eleanor into a clothing store, suggesting she try on some sexy high heels and a cocktail dress for him. Recognizing Taylor from seeing him on television, she almost swoons as she stumbles into the fitting room, yanking Taylor in after her. Later, while playing poker, Taylor offers to let Ned out of the bet. Ned refuses, crowing Taylor cannot seduce Veronica. The answering machine activates with Veronica inviting Taylor on a double date with Ned and Claire. During dinner, Taylor finds himself staring at a life-size portrait of a nude Veronica, who brags about her many accomplishments as a musician. Realizing this is a test, Taylor tells her to shut up. To Ned’s chagrin, Veronica bursts into laughter. She gets rid of Ned and Claire as soon as possible and jumps into bed with Taylor. However, sex is a disaster. Veronica leaves to take a shower and asks Taylor to leave. Taylor forgets his watch. The next day, after having sex with Eleanor in the studio garage, Taylor arrives at Erin’s home and encounters football player Tarry Childs, who threatens to kill him if he hurts Erin’s feelings. Erin takes Tarry aside and tells him Taylor is the first man who has not tried to sleep with her on the first date. Tarry declares that he never made a pass at her, but she tells him it does not count as they are only friends. Weeks go by and Taylor receives a message from Veronica inviting him to retrieve his watch at a concert hall. At the box-office, Taylor is surprised to find a ticket waiting for him. He is mesmerized by Veronica’s piano concert until he spots Ned sitting next to Eleanor. Eleanor chases Taylor into the lobby, drags him into a closet, and tears off his clothes. Later, Taylor leaves the closet and runs into Eleanor’s husband, Howard Larimore, who declares he is a big fan of Taylor’s weather reports. Eleanor’s son, Howard, Jr., arrives and loudly points out that Taylor’s zipper is down. That night, Taylor arrives at Veronica’s apartment with roses, but she refuses to let him in because he did not stay to compliment her after the concert. Taylor compliments her playing and tells Veronica he cannot wait to hear her again. Veronica slides one of her albums under the door to him and tells him to call her. Weeks pass and Taylor takes Erin to see her favorite movie, Snow White . Afterward, Taylor sets up a video camera and proposes. Erin says “yes” and demands Taylor ravish her. Before Taylor turns off the camera, he whispers into the microphone that he is one third of the way to winning Claire’s Picasso and is about to have sex with a goddess. However, Erin confesses to being a virgin, so Taylor tells her they should wait until the honeymoon. Hoping to duplicate his success, Taylor takes Veronica to see Snow White and the Seven Dwarfs. However, Veronica declares the movie is perpetuating the myth that a woman is incomplete without a man. Taylor reminds her of the tale of “The Frog Prince,” which is about men needing women to change them from frogs to princes. This arouses her, and they go home to make love. The next morning, Taylor and Veronica are in bed watching the Eagles football game on television when the cheerleaders unfurl a banner congratulating Erin and Taylor. Before Veronica can see it, Taylor kisses her. The answering machine activates and Taylor hears Eleanor calling to set up a luncheon date to discuss Veronica performing at a charity event. As the three month deadline approaches, Taylor meets Erin at a restaurant, hoping to break off the engagement by claiming he is sterile. However, Erin asks if she can have time to think about this development. The next day, Taylor takes Eleanor to see Snow White, but halfway through the movie she drags him to a hotel room. Taylor sets up the video camera, and pretending they are playing a sex role game, gets Eleanor to say she will be his “bride.” That weekend, Taylor takes Veronica to his cabin in the country. After days of being together, Taylor realizes he is in love with Veronica. However, he still hides a camera in some trees and proposes. She suggests they live together first, but Taylor insists she has captured his heart and she agrees to marry him. Taylor attempts to tell Veronica about the bet, but she does not want to hear about his past. They set the wedding date for Saturday. Back in the city, Erin confides to Tarry Childs that Taylor is impotent, then has sex with the football player to see what she is giving up. Later that day, Veronica is at Claire’s house with Eleanor to plan the charity event. Although Veronica promised to keep the engagement secret, Claire figures out she is getting married. Claire hears her two children fighting over a videotape. The three women are shocked when she puts it into the machine and they see Taylor proposing to Erin and bragging he soon will have Claire’s Picasso. Across town, Taylor announces he is getting married for real and calls off the bet. He first sends a “Dear Jane” letter to Eleanor suggesting she should put her passion into her marriage. Next, he goes to a restaurant to meet Erin, expecting her to cancel the wedding. However, he finds Veronica, Claire, and Eleanor sitting nearby. Rushing into the lobby, Taylor telephones Erin. She tells Taylor she will give him her answer Saturday morning at her place. That Saturday, Taylor walks into Erin’s house to find a surprise bridal shower. One by one, family and friends offer their condolences on Taylor’s impotency. Taylor runs away. He arrives at home, to discover Eleanor has moved in. She assures him that domesticity will not spoil their sex life and tears off her dress to reveal a dominatrix outfit beneath. Taylor runs into the bathroom and finds Howard, Jr. in the bathtub. He changes into his tuxedo and runs outside to find his tires slashed. Claire drives up in a station wagon full of small children and asks if he needs a ride. Taylor squeezes in and is soon covered in ice cream. When Claire drives past the church, Taylor leaps out and rushes to the altar seconds before Veronica marches down the aisle. At the altar, Veronica declares she will never marry Taylor and runs away. A month later, Ned finds Taylor surrounded by empty liquor bottles and food containers, watching his proposal to Veronica. Ned convinces Taylor he should ask Veronica to forgive him. At a charity auction, Veronica is onstage offering a private concert. Taylor appears and outbids everyone. Veronica insists he publicly declare he is a creep. Taylor jumps on top of a table and begs her to marry him. She agrees, and the couple receives a standing ovation.