Architect Natalie develops a strong hatred for romantic comedies at an early age, which is exacerbated by her low self-esteem and difficulty in finding love. Her assistant Whitney, a fan of romantic comedies, believes their co-worker Josh is in love with Natalie, but Natalie dismisses the notion because Josh appears to spend all his time staring at a billboard model across the street. One day, Natalie is knocked unconscious during an attempted mugging and finds herself trapped in the stereotypical romantic comedies that she despises. Whitney becomes her enemy and her neighbor Donny becomes a flamboyant homosexual friend offering advice, while Blake, a billionaire client of her company, develops a romantic interest in her. Additionally, Josh enters into a relationship with the billboard model, who identifies herself as a “yoga ambassador” named Isabella.
Desperate to return to her reality, Natalie deduces that in the tradition of romantic comedies, she can only leave by finding true love. When her relationship with Blake turns sour, Natalie recognizes that she has feelings for Josh, who has become engaged to Isabella. Natalie attempts to stop their wedding, but soon realizes that instead of loving another person, she needs to learn to love herself. Following this revelation, Natalie gets into a car accident and loses consciousness.
Natalie wakes up in the real world, but with new self-confidence, which she uses to successfully propose an idea to Blake. After reuniting with Josh, she learns that he has not been staring at the model, but at Natalie’s reflection, and the two begin a relationship. As Natalie prepares to head home, Whitney tells her that despite her dislike for romantic comedies, everything she just experienced has been comparable to one. Realizing that she has been in a romantic comedy the entire time, Natalie and the rest of the characters proceed to engage in a rendition of “Express Yourself”.