Film

Chasing Amy

Name: Chasing Amy
Genre: Comedy, Drama, Romance
Released: 1997
Cast: Ben Affleck, Joey Lauren Adams, Jason Lee, King Mustafa Obafemi, Jason Mewes

Kevin Smith's 1997 comedy about a comic-book artist who falls for a lesbian peer, then sets out to change her mind. It's funny and self-aware about its own bad ideas, nakedly earnest about desire and jealousy, occasionally clumsy but never cynical. For anyone who's felt stupid about love, or watched a friend do the same.

TMDb rating

3.4

Should you watch it?

Watch it if you like talky, profane romantic comedies where the jokes come from characters arguing about comics, sex and honesty, and you don't mind being made uncomfortable along the way.

Skip it if you need your romance sweet and your dialogue restrained, since the characters discuss sex and identity at length in frank, sometimes crude terms.

What it asks of you: At just under two hours, it talks more than it moves and lets long conversations circle back on themselves, its mood swinging from raucous to wounded without much warning.

Not sure? Find tonight's pick in a minute.

If you liked this

Before Sunrise1995

Two strangers meet on a train and spend a night walking Vienna talking about everything. Like Chasing Amy, it's about the electricity of connection and how much of love is just conversation and the illusion of perfect understanding.

But It's very talky and deliberately slow. There's no plot twist or external conflict—just two people talking until morning, which some find tedious.

Clerks1994

Kevin Smith's debut about gas station workers wrestling with relationships, ambition and whether they're wasting their lives. Same director, same voice: cheap, funny, sincere, unafraid to let characters be flawed and yearning.

But Shot in black-and-white on a microscopic budget. The acting is uneven and the dialogue can feel performative—it's very much a film, not life.

Reality Bites1994

Winona Ryder navigates love, friendship and existential dread in post-college limbo. Captures that same era's specific brand of romantic confusion and the ache of wanting someone who doesn't want you back the way you need.

But The '90s irony can feel dated. The love triangle resolves in a way that sits uneasily now, even if it felt transgressive then.

Not sure tonight? Get a pick in a minute, starting from Chasing Amy

The wildcard

Something you would not have found on your own.

Bitter Lake2015

Both explore the delusion of belief—Holden believing he can change Alyssa, America believing it can reshape the world. Both are about the gap between fantasy and reality, told with surprising tenderness.

Adam Curtis's hypnotic documentary about Western intervention in Afghanistan, framed around an impossible love story that parallels geopolitical fantasy. Like Chasing Amy, it's about how we fall in love with ideas of people rather than people themselves.

But It's avant-garde and politically dense, with no conventional narrative. Three hours of fragmentary storytelling may feel punishing if you want something straightforward.

Eternal Sunshine of the Spotless Mind2004

A man erases memories of his ex-girlfriend from his mind, then realizes he was happier in the relationship's worst moments than without her. It's about how we mythologize and revise people we love, just like Holden does with Alyssa.

But It's deliberately fractured in structure and quite melancholy. If you want straightforward storytelling or a lighter touch, this will feel pretentious and slow.

Eternal Sunshine of the Spotless Mind poster

High Fidelity2000

John Cusack's record-store owner obsesses over exes and the nature of romantic compatibility. Funny and self-lacerating about how we construct narratives around people to make sense of why they leave us.

But The protagonist is immature and self-absorbed, which is partly the point, but it can grate. The film doesn't always hold him accountable the way it should.

Mallrats1995

Another Smith film about young men navigating romance and friendship, lighter and weirder than Chasing Amy. Banky Edwards' prequel of sorts, and it's got genuine affection for its knucklehead characters.

But It's deeply silly and occasionally punches down. The plot is thin and the filmmaking is pretty crude, even by Smith's low standards.

Knocked Up2007

A one-night stand becomes a pregnancy, forcing two incompatible people to reckon with connection and responsibility. Like Chasing Amy, it's messy about desire and asks whether love can overcome fundamental incompatibility.

But The gender politics are unexamined in ways that feel worse with time. Some characters exist mainly to prop up the male lead's journey.

Say Anything...1989

A working-class guy falls for the class valedictorian despite every obstacle. It's about romantic persistence done with genuine heart, and it understands why someone might make a fool of themselves for another person.

But It's unabashedly sentimental, which reads as corny if you're not in the mood. The gender dynamics are pretty old-fashioned.

The Good Girl2002

Jennifer Aniston in a dark dramedy about a woman trapped in a dull marriage and small-town life who has an affair. Explores how we project fantasy onto people and mistake desire for connection, like Holden does.

But It's bleak and doesn't offer much catharsis. The protagonist makes bad choices and mostly suffers for them, with no real redemption.

Portrait of a Lady on Fire2019

The inverse of Chasing Amy's romantic failure—here, two women allow themselves to want each other, and the film honors that without shame. Same emotional stakes, opposite outcome.

A French painter and her aristocratic subject fall in love over weeks of sitting together. It's achingly tender about desire, touch, and the intensity of connection between two women. Painterly, sensual, and devastating.

But It's very slow and visual rather than verbal. If you need plot momentum or dialogue-driven scenes, the long silences and gazes will test your patience.

Synecdoche, New York2008

Like Chasing Amy, it's about a man convinced he can rewrite someone else's reality through force of will. But where Smith is earnest, Kaufman sees it as pathology—a funhouse-mirror version of the same mistake.

Charlie Kaufman's fever dream about a theater director who becomes obsessed with replicating reality in art, losing his ex-wife and identity in the process. Hilarious and crushing about how we turn people into projects and stories.

But It's confusing, pretentious, and deliberately messy in its narrative. If you're not patient with ambiguity and emotional abstraction, it will feel like a chore.