The film opens with Ethan Cooper Wesley Elder, a quiet clerk at a computer repair shop, narrating to his roommate Sam Osric Chau about his long-lasting infatuation with Emily Atkins Christina Grimmie, the girl he has known since elementary school.
One day, while visiting his sister Lexy Shawna Howson, a florist, Ethan is approached by Mrs. Taylor Victoria Jackson with a tempting assignment: break up her daughter Veronica’s boyfriend in exchange for money. He completes the task, but in doing so, Veronica becomes enamored with him instead. This unexpected turn of events makes Ethan a sought-after “match-breaker” in the eyes of disapproving parents, and Mrs. Taylor starts sending him to other families, which fuels his growing, if uneasy, success.
Sometime later, another dissatisfied parent comes calling. Ethan meets the client at a jazzy venue where she sings by night, only to discover that the daughter is Emily Atkins Christina Grimmie, the very girl he’s been obsessed with since childhood. Intrigued, Ethan resolves to see her again, this time at the art gallery where Emily works, and the two reencounter with a mix of curiosity and old memories.
Meanwhile, a pretentious, wealthy young man named Mitchell Olan Rogers takes a fancy to a waitress named Tricia Tessa Violet. His parents, wary of such a match, hire Ethan to dismantle the couple. Ethan agrees and even goes on a double date with Mitchell and Tricia, bringing Lexy along to pose as his girlfriend. They try to push the two apart, but the plan backfires as the couple proves resilient.
Afterwards, Emily invites Ethan to a restaurant, where he learns that she isn’t as flawless as he imagined and that she is quietly unsettled about her relationship. In a twist, Emily’s mother Donna Jennifer Mays offers Ethan a reward for his efforts, but he declines and instead focuses on the evolving dynamic with Emily. As they spend time together, Emily learns that Ethan’s crush on her runs deeper than a casual fixation, and Ethan discovers that she isn’t perfect, even if her imperfections still pull him in.
A new turn comes when Emily gets a call from a friend in need and asks Ethan to come to her aid. Through this connection, he learns that Tricia is a close confidante of Emily, and that Tricia and Mitchell have already broken up. Frustrated by Veronica’s persistent attention, Ethan decides to tell her he has no interest in continuing their arrangement.
The drama peaks at a formal party, where Emily spots a check her mother made out to Ethan tucked in her handbag. Ethan races to the party after a text from Sam warns that someone is trying to move in on Emily. Upon arriving, Emily confronts him about the check, and Ethan realizes Veronica has followed him. In a public confrontation, Veronica unveils Ethan’s reputation as a match-breaker, revealing how long she has stalked him since their first encounter.
The next day, Emily’s mother explains that Ethan refused to accept the check intended to dismantle the couple. Overcome with guilt but determined to repair the situation, Ethan helps mend the broken connection between Mitchell and Tricia, even inviting Mitchell’s father, a record producer, to visit the jazz club that night where Emily is performing. In a telling moment, Tricia tells Emily that Ethan’s intervention helped bring Mitchell back to her.
Six months pass in a montage that shows Tricia and Mitchell engaged and Ethan embarking on a new chapter: he has written a relationship guide and has begun a genuine romantic relationship with Emily, suggesting a new, more hopeful future for both of them.
