How to Fall in Love

The film opens with Harold White, a shy accountant whose mother still fusses over his appearance before dates. After a series of dating disasters, Harold's friend Willy suggests he hire a dating coach. Meanwhile, Annie Hayes, a talented but struggling event planner, has moved back in with her sister Claire and is working as a waitress to make ends meet. Harold and Annie, who attended high school together, reconnect when Harold visits the diner where she works. Learning of Harold's dating woes, Annie offers her services as a dating coach to help pay off her debts and save for a new apartment. The coaching sessions begin with Annie focusing on Harold's self-image, forcing him to repeat the mantra 'I look good' and encouraging him to embrace his passions for vintage music, cooking, and photography. Harold begins to transform, improving his fitness and wardrobe. He eventually uses Annie's 'ice-breaking' techniques to ask out Julie, a woman he frequently sees at a coffee shop. While Harold and Julie begin a relationship, Annie finds herself feeling unexpectedly jealous. A pivotal moment occurs when Harold and Annie scout a romantic restaurant in the city; they share a dance and Harold reveals that he has harbored a crush on her since a freshman homecoming dance where he felt rejected. During a 'lesson' on intimacy, the two share a practice kiss that clearly affects them both. The conflict escalates when Annie helps Harold get a photography gig for a park fundraiser she is planning, but a misunderstanding arises regarding Annie's high school rival, Matt Schneider. Harold believes Annie is interested in Matt, while Annie believes Harold is happy with Julie. In reality, Harold and Julie break up after realizing they have nothing in common, as Julie dislikes Harold's 'old-fashioned' romantic nature. The resolution occurs at the fundraiser event. After Claire's daughter Megan reveals to Harold that Annie called him the 'man of her dreams,' Harold rushes to the party. He gives a public speech praising Annie's talents and declaring his love for her. The movie ends with the two dancing to 'their song,' finally united as a couple.