While studying at a college in New York City, sophomore Al (Freddie Prinze Jr.) and freshman Imogen (Julia Stiles) embark on a blossoming romance after meeting at a bar. This budding relationship encounters a mix of friends and challenges as they navigate their feelings. Imogen's friend Lana is part of the backdrop, and although Al and Imogen share a beautiful dance, complications arise when another student, Jim, also vies for Imogen's attention.
Despite her initial hesitation about relationships in her freshman year, Imogen finds herself hugging Al at the end of the night, marking the start of a whirlwind romance. Al soon makes his way to Imogen’s dorm room, where he discovers her passion for art and her impressive portfolio that includes self-portraits on album covers. The duo engages in a playful fake therapy session as they unveil their interests and past dating experiences.
Things escalate when Al introduces Imogen to his parents, Ray and Judy (played by Lucie Arnaz), who enjoy their time together. After three months of passionate dating, they find themselves deeply in love, each experiencing their first true romance. Imogen, an aspiring artist, organizes a private showing at an art gallery as a surprise for Al's birthday, leading to an intimate moment that marks the height of their early relationship.
However, not all is peaceful; Al's roommate Monk (Zak Orth), who has transitioned into the world of adult films, claims that love is just an illusion, creating a ripple of doubt for Al. Monk's flirtatious co-star, Cyrus (Selma Blair), adds to the tension when she expresses her interest in Al, just as he grapples with a bet that forces him to partake in Monk's film.
As Al prioritizes his time with Imogen over the project, their world begins to crack when Imogen plans a summer in France and faces unexpected questions about their future. Al's father, Chef Ray (Henry Winkler), envisions a culinary TV show with his son after Al's graduation, but Al dreams of mastering French cuisine instead. Concerned about their drifting connection, Al organizes a countryside picnic that unwittingly results in an accident, prompting a joint determination to salvage their bond.
However, challenges arise as Imogen refuses intimacy one night, leaving Al feeling inadequate. The situation worsens with false pregnancy fears and moments of temptation with Cyrus, leading to growing tensions and heartbreak. Following a chaotic breakup after Imogen’s confession about Jim, she relocates to San Francisco to continue her studies.
Upon graduation, Al spirals into depression, struggling with the disintegration of his relationships, notably with Monk, who becomes preoccupied with his writing career. Following a series of misguided attempts to move on—including a reckless stint with Cyrus—Al finds himself lost and drinking too heavily in an attempt to forget Imogen.
During a party thrown by his parents to lift his spirits, he has a chance encounter with Imogen, who has blossomed into a talented cover artist. Their heartfelt reconnection reignites old flames, and they both acknowledge the importance of their young love. With dreams still alive, Al takes a position at a prestigious restaurant in San Francisco, promising to surprise Imogen with a romantic evening, signaling their willingness to start anew together.
