Lucy Neal (Lucy Hale) struggles with intimacy in her relationship with her boyfriend, Jeff, leading to their breakup after she discovers his porn habit. As a member of a string quartet, Lucy experiences a breakdown at a wedding performance, prompting her to create a list to tackle her intimacy issues. Her journey includes watching porn, reading racy novels, visiting a sex store, and attending a strip club. At subsequent events, Lucy meets and grows attracted to Grant, a wedding guest. They start dating, leading to a series of embarrassing yet enlightening experiences involving sexual exploration and misunderstandings, such as Grant mistakenly thinking Lucy was pregnant due to her comfort-oriented pregnancy pants. Despite setbacks, including a failed Philharmonic audition and her ex-boyfriend Jeff’s wedding, Lucy finds happiness with Grant. She playfully hires a porn star to surprise Jeff at his wedding, and the story concludes with Lucy and Grant reconciling and continuing their romantic and sexual exploration.