A young woman named Molly Gordon, playing Iris, begins the story in a state of panic, rushing to her friend Geraldine Viswanathan, who portrays Max. Iris is visibly distressed and shows Max that she has handcuffed her boyfriend, Isaac, to the bed, revealing that something unusual has happened. The film then takes us back to 33 hours earlier, when their romantic weekend adventure begins in the small town of High Falls—though Iris mistakenly calls it “O’High Falls” due to a loose piece of the welcome sign.
Earlier that day, Iris and Isaac, played by Logan Lerman, start their trip at a strawberry stand, where a flirtatious exchange occurs between Isaac and the vendor. Iris notices the tension but decides to dismiss it. After purchasing strawberries, Isaac offers to drive, and on the way, they accidentally drive into the strawberry cart, resulting in a car full of strawberries and a humorous start to their weekend. Their destination is a quiet rental house near a tranquil lake, offering a scenic backdrop for their getaway.
Throughout the day, their interactions are sweet and playful. They take a swim in the lake, where they are observed by Steve (David Cross), the nosy neighbor who warns them against having sex in the water. Later, Isaac prepares dinner, and the two share a dance outside, immersed in a romantic moment. The mood shifts when Iris discovers belongings of the house’s previous owners, including some bondage gear. Curiosity leads to intimacy, and they share an intimate night, with Iris cuffing Isaac to the bed in a moment of affection.
However, the tenderness is short-lived. Isaac reveals that he’s not looking for a committed relationship and confesses that he has been seeing other women, which strikes a nerve with Iris. Feeling hurt and betrayed, she leaves him cuffed, and her mood quickly turns from love to confusion and frustration. That night, Iris seeks advice from a dating guru through her phone, making a vow that she will give Isaac 12 hours to decide if he truly wants to be with her.
The next day is a mixture of awkward attempts at reconnecting and comedic misadventures. Iris tries to cook breakfast, asking the friendly neighbor Steve for an egg, and prepares a quirky dish for Isaac. She makes emotional efforts to bond, even going as far as to hold his pee while he uses a bowl, trying to break his emotional defenses. There’s a slight breakthrough when Iris performs a dance from her past, but things quickly derail when Isaac calls her crazy and threatens to uncuff her.
Iris calls Max, hoping to bring her into the situation, but is surprised to find that Max has brought her boyfriend, Kenny, with her. Tensions rise when Max accidentally reveals Isaac's predicament, showcasing the predicament Iris has created—effectively kidnapping her boyfriend. The group’s plans become more complicated as they try to figure out their next move, with Isaac refusing to eat dinner out of suspicion that Iris might poison him.
Desperate to reverse the situation, Max contacts her cousin, who claims to be a witch. They concoct a plan involving a mysterious “witch’s brew” to erase Isaac's memory of the recent events. Using Kenny as a guinea pig, they perform a ritual outside to ensure the potion works, hoping to free Isaac from his amnesia and the ordeal he’s endured.
A flashback reveals a tender moment from one of Iris and Isaac’s earlier dates, where Iris, having had a bad day, finds comfort in Isaac’s support, culminating in a heartfelt kiss. Later, Iris sets up a romantic scene before abruptly telling Isaac she hates him, illustrating the complex emotions swirling between them.
When Isaac wakes up, he appears to have forgotten the past two days, still cuffed to the bed but unaware of the chaos. Iris, hopeful, agrees to uncuff him, but Isaac quickly figures out something is wrong. Feeling suspicious, he overhears a plan from the previous night and makes a run for it, escaping into the rain. Meanwhile, Iris, feeling responsible, stays behind, convinced she’s ruined everything.
The story reaches a climax when the local sheriff informs Iris that her car was found crashed into a tree, but Isaac is missing. Together with Max and Kenny, she searches for him in the woods. Eventually, they find Isaac, who explains that he managed to escape after the car hydroplaned and crashed while he was injured and unable to walk. As they wait for help, Iris and Isaac have a heartfelt conversation about their relationship, realizing that they are better off apart. Despite the pain, they mutually agree that their time together was meaningful but not sustainable.
As the ambulance arrives to take Isaac away, Iris remains behind, reflecting on the tumultuous weekend in the small town of High Falls, a place that saw the beginning and end of their complicated relationship. The film closes with a quiet acknowledgment of the emotional rollercoaster they endured, highlighting themes of love, misunderstandings, and the importance of knowing when to let go.
