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Plot Summary


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.

Timeline


Meeting at the Bar

Sophomore Al and freshman Imogen first cross paths in a lively New York City bar. Their connection is immediate, setting the stage for a blossoming romance filled with excitement and challenges.

New York City

The Dance

Al and Imogen share a beautiful dance, a moment that captures the essence of their budding relationship. This dance signifies the start of their emotional journey together amidst a backdrop of friends and romantic complications.

Bar

Al Visits Imogen's Dorm

Intrigued by Imogen's artistic flair, Al visits her dorm room and discovers her impressive portfolio. They engage in playful conversation, revealing their interests and past experiences during a mock therapy session.

Imogen's Dorm

Meeting Parents

Al introduces Imogen to his loving parents, Ray and Judy. Their acceptance and enjoyment of Imogen highlight the deepening bond between the couple as they navigate their relationship.

Al's Family Home

First True Love

After three months of passionate dating, Al and Imogen realize they are experiencing their first true romance. Each moment together solidifies their connection and deepens their love for one another.

Art Gallery Surprise

Imogen organizes a surprise private showing at an art gallery for Al's birthday, showcasing her talents and their relationship's significance. This event marks a high point in their early romance, filled with intimacy.

Art Gallery

Doubts Arise

Al's roommate Monk creates uncertainty about love, claiming it's an illusion, impacting Al's perception of his relationship with Imogen. This doubt is compounded when Cyrus, Monk's co-star, shows interest in Al.

Summer Plans and Tensions

As Imogen plans to spend the summer in France, questions about their future surface, leading to increased tension in their relationship. Al, facing challenges in his own aspirations, feels the pressure mounting.

Countryside Picnic Accident

In an attempt to reconnect, Al organizes a picturesque countryside picnic. However, an unexpected accident during the outing serves as a wake-up call for both, highlighting their need to address their issues.

Countryside

Intimacy Refusal

Imogen's refusal to engage in intimacy one night leaves Al feeling rejected and inadequate. This emotional rift leads to misunderstandings and further complications in their relationship.

Breakup and Relocation

After a chaotic breakup triggered by Imogen's confession about Jim, she decides to move to San Francisco for her studies. This separation sends Al into a downward emotional spiral, deeply affecting both their lives.

San Francisco

Al's Post-Grad Struggles

Following graduation, Al struggles with depression fueled by the dissolution of his relationship with Imogen and his friend Monk. His misguided attempts to distract himself lead him down a reckless path.

Rekindling at the Party

At a party thrown by his parents to cheer him up, Al unexpectedly encounters Imogen, who has grown into a talented artist. Their heartfelt reconnection sparks old feelings and signals hope for a renewed relationship.

Al's Family Home

New Beginnings

With their dreams still alive, Al accepts a position at a prestigious restaurant in San Francisco. He plans a romantic evening for Imogen, indicating their willingness to embark on a new chapter together.

San Francisco

Characters


Al (Freddie Prinze Jr.)

Al is a charming sophomore navigating the complexities of young love amid academic pressures. His earnestness and creativity propel his relationship with Imogen, showcasing both his adventurous spirit and vulnerability as he deals with doubts and insecurities.

💖 Romantic 🎓 College Student 🤔 Introspective

Imogen (Julia Stiles)

Imogen is a talented freshman artist who embodies passion and creativity. Her character reflects both the excitement and challenges of new relationships, as she balances her commitment to art with her growing feelings for Al, showcasing her independence and warmth.

🎨 Artistic 💕 Romantic 🌱 Growth

Setting


Time period

Modern Day

The movie takes place in a contemporary setting, reflecting the experiences and challenges faced by college students today. Themes of young love, self-discovery, and relational complications resonate with the realities of modern romance.

Location

New York City, San Francisco

New York City serves as the vibrant backdrop for Al and Imogen's college romance, known for its bustling life, diverse culture, and iconic landmarks. Meanwhile, San Francisco represents a new chapter, characterized by its scenic beauty, artistic communities, and the famous Golden Gate Bridge, becoming a crucial location for Imogen's growth as an artist.

🏙️ City 🌉 Coastal City

Themes


💔

Young Love

The film explores the ups and downs of young love, portraying the passion and excitement that often accompany first relationships. Al and Imogen's journey is filled with naive hopes and heartbreaking realizations, showing both the beauty and fragility of love at this stage of life.

🎨

Artistic Ambition

Imogen’s passion for art highlights the theme of ambition and personal growth. As she navigates her college experiences, her artistry resonates with her emotional journey, illustrating how creativity and love intertwine in shaping one's identity.

🎭

Identity Crisis

Both Al and Imogen grapple with their identities throughout the film, navigating their romantic lives while figuring out their future aspirations. The challenges they face prompt them to confront their desires and fears, leading to insightful self-discovery.

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