Lucy Neal, portrayed by Lucy Hale, faces a significant challenge in her relationship with her boyfriend Jeff, played by Stephen Friedrich, as her inability to express intimacy leads to disappointment. One night, while Jeff is asleep, Lucy sneaks a look at his laptop and discovers that he has been watching porn. This revelation triggers a heated argument, in which Jeff unhelpfully compares porn stars to Lucy and her group of violinists, ultimately leading to their breakup. As Jeff moves out, Lucy finds herself drowning in confusion and sadness.
For comfort, Lucy turns to her violinist friends—Nessa (Jackie Cruz), Priscilla (Mindy Cohn), and Paul (Adhir Kalyan)—but during a wedding performance, her emotional pain bubbles over. Overwhelmed, she confesses to her friends that Jeff left her due to her failure to fulfill his desires. Struggling to understand men who indulge in pornography or frequent strip clubs, just like Paul does, Lucy is encouraged by her friends to take proactive measures. In response, she devises an intriguing sex list to tackle her intimacy issues. This list includes challenging tasks like watching 25 porn films, visiting a sex store, reading erotica, exploring a strip club, and even consulting a sex expert.
At a wedding, after drinking too much, Lucy vents her frustration aloud about saying the word "cock" in a public setting, which catches the attention of Grant (Leonidas Gulaptis). He approaches her to offer comfort, leading to a friendly exchange that helps her regain her composure. Embarking on her list, Lucy starts with movie marathons and erotic novels at home. The following day, her friends visit, but instead of wallowing in misery, Lucy invites them to a sex shop, where her paths cross again with Grant.
Their chemistry grows as they engage in playful banter at the store, and Lucy feels a budding attraction to him. Later that evening, she accompanies Paul to a strip club where she is captivated by the performances on stage, but things take an awkward turn when she attempts to tip a dancer with her meager funds, resulting in both of them being escorted out.
Soon after, Lucy's group performs at another event, where an unexpected wardrobe malfunction involving her vagina beads complicates matters more. During this event, Grant approaches her and asks for a dance, culminating in an embarrassing yet exhilarating public display of emotion. Following this intimate moment, Grant invites her for dinner, a proposition Lucy eagerly accepts.
However, when Lucy encounters Jeff again, he harshly grades her sexual performance in bed with a "D," further complicating her self-esteem issues. In a quest for self-improvement, she attends a sex seminar, while also preparing for an upcoming audition with the philharmonic orchestra.
Lucy’s dinner date with Grant unfolds into another adventure when they attend a live taping of Dr. Becker's talk show—thanks to tickets from Priscilla. Here, the renowned sex expert, Madam Swarovska, addresses Lucy’s lack of experience in a candid manner, urging Grant to take the lead in opening her up to new sexual experiences.
After another rendezvous, things get uncomfortable when Grant discovers the amount of sexual paraphernalia scattered throughout Lucy's bedroom, leading to his hasty exit. Lucy, feeling embarrassed, decides to rid herself of all those items as she continues to focus on her violin practice for her audition.
As the days progress, Lucy learns of Jeff's impending marriage, prompting her to agree to perform at his wedding—a decision motivated by her desire to confront her past. Meanwhile, she joins Paul on a spontaneous trip to Vegas, aiming to fulfill her brothel visit goal. However, Paul backs out, leaving Lucy undeterred despite the brothel's refusal to accommodate women.
During another night out at a bar, Lucy finds herself unexpectedly signed up for a talent show, and to her surprise, she plays the violin passionately, impressing the audience. As she reconnects with Grant, they realize the misunderstanding that strained their earlier connection and decide to reignite their romance. Finally, Lucy receives disappointing news regarding her audition, yet she finds solace in the joy of her relationship with Grant.
At Jeff's wedding, in a bold move, Lucy hires Honey, a well-known porn star, to surprise Jeff, knowing his interest in her. When Jeff spots Honey, he panics, fearing his new wife will notice her, prompting his hasty retreat. In the end, Lucy embraces her newfound relationship with Grant, daring to explore the last item on her list together.
