Wesley Darya, Nasim Pedrad, begins her journey facing a series of comically unfortunate events that set the tone for her chaotic adventure. Her day starts with a job interview at a Catholic school for a guidance counselor position. Unfortunately, her candid honesty about sex talk with the head nun causes her to bomb the interview, leaving her feeling frustrated and embarrassed. Her friends, Brooke (Anna Camp) and Kaylie (Sarah Burns), try to lift her spirits at Kaylie’s house, only for car trouble—a broken transformer falling on Wesley’s vehicle—to add to her misfortunes.
Deciding to move on from her bad luck, Wesley goes on a blind date arranged by Kaylie’s husband, Tad (Scott Rodgers), and meets Sean McGuire, played by Lamorne Morris, at a local bar. Their initial chat is lively, but Sean quickly pulls away when Wesley startles him by rushing into topics about marriage and children. She reveals her recent hardships—struggling to find a job, her ex getting married, and losing her pet birds—highlighting her emotional turmoil. As she storms out, her heel gets lodged in a crack causing her to trip and lose consciousness. She wakes up unexpectedly in the company of Jared Sterling, a charismatic stranger played by Robbie Amell, who invites her back to his place so her friends can pick her up.
Wesley is smitten with Jared, and it appears he shares her attraction, which leads her to pursue a budding relationship. Over the course of a month, their chemistry deepens and they become physically intimate. However, things take a turn when Jared suddenly falls silent, and Wesley, feeling ghosted, becomes despondent. In her drunken frustration, she, Brooke, and Kaylie send Jared a harsh email filled with crude insults and references to his deceased father. When Jared finally calls to explain that he’s been in a coma in Mexico after a car accident, Wesley realizes her mistake. The email had already gone out, and she escalates her desperation by proposing a risky plan to break into Jared’s hotel room in Mexico to delete it.
Traveling to Mexico, Wesley’s trip descends further into chaos. Her awkward arrival is marked by a mishap when her bag drops and a dildo is revealed, which a young boy named Nolan, played by Toby Grey, quickly notices. Nolan’s mother, Debbie (Jessica Chaffin), becomes furious at Wesley for her apparent inappropriate behavior. To make matters worse, Sean is also vacationing at the same resort, but Wesley avoids him. The situation spirals into a series of comic misadventures, including Wesley trying to sneak into Jared’s room with the help of her friends and an unsuspecting resort employee, often hiding under a towel to evade detection. In one mishap, Wesley’s towel falls off, nearly exposing her to Nolan and Debbie, who mistakenly think she’s a pedophile.
While trying to retrieve the master key to Jared’s room, Wesley gets involved in several bizarre incidents, like a dolphin hump incident while attempting to paddleboard with Sean, and a subsequent fainting spell caused by exhaustion and sickness. During her unconscious state, she’s helped by Nolan, who instead of calling the police, surprisingly bails her out of jail because of his affection for her. Wesley confronts her own reckless choices, but she remains stubborn, determined to fix her mistake by getting into Jared’s room to erase the embarrassing email herself.
Her relentless pursuit leads her into more trouble—she gets electrocuted trying to climb a fence and is eventually caught by Jared’s hotel staff. Her friends, Brooke and Kaylie, arrive to bail her out, witnessing her arrest firsthand. Meanwhile, her friends decide to seek some peace and clarity at a meditation retreat led by Angel de la Paz (Heather Graham). Kaylie hopes the guru can help her conceive, while Brooke confides her frustrations about her marriage. The two women bond over their personal struggles, with Brooke ultimately beginning a romantic relationship with Angel.
Back in Mexico, Wesley’s obsession with Jared culminates in a covert attempt to follow his departure. She and Sean bond further during a celebratory quinceañera, where Wesley’s feelings deepen. She tries to orchestrate a plan to catch Jared before he leaves, convincing herself that she still loves him despite everything. During the flight back to Los Angeles, Wesley’s attempt to delete the email fails when Jared discovers it. Outraged by her antics and dishonesty, Jared ends their relationship, leaving Wesley feeling both devastated and孤独.
In the aftermath, Wesley secures a new position as a guidance counselor after impressing at a school, signaling a fresh start. She visits Kaylie’s house to find her and Tad, who are preparing to sell their home. In an awkward, humorous moment, Wesley climbs a tree to retrieve Kaylie’s cat Kevin, only to see Kaylie and Tad inside with a pregnant woman—only to realize they’re just selling the house and not expecting a baby. Despite feeling humiliated, Wesley’s friends forgive her earlier misadventures.
Her story concludes with her visiting the same restaurant where she first met Sean, attempting to reconcile her feelings. She encounters Sean on a blind date with another woman, who shares a wild story about her own chaotic dating life. When Sean leaves the date to chase after Wesley, he kisses her, hinting at a possible new beginning. Through her turbulent journey, Wesley learns valuable lessons about love, self-acceptance, and the importance of true friendship, even in the midst of absurd and unpredictable chaos.
