Film

Carrie Pilby

A sharp 19-year-old intellectual misfit in New York, armed with sky-high standards and cutting disdain, tries to navigate love and friendship for the first time. Bel Powley is wonderful: watchful, funny, prickly without being insufferable. It's a coming-of-age story that trusts you to like someone difficult.

TMDb rating3.4

Should you watch it?

Watch it if you enjoy a prickly, self-certain heroine whose wit is sharper than her social instincts, and you like comedy that stays close to loneliness without tipping into sentimentality.

Skip it if you want a brisk, plot-driven romance; this one is talky and built around a young woman's inner monologue, so its gentle episodes can feel slow and repetitive.

What it asks of you: Ninety-eight minutes of mostly quiet conversations and awkward encounters, with its humor arriving in dry asides rather than big set pieces, so it rewards steady attention.

If you liked this

Eighth Grade2018

Another precise portrait of a brilliant teenager learning that other people are more interesting than her ideology. Bo Burnham finds comedy and tenderness in the same uncomfortable places.

But Secondhand embarrassment is the whole point. Some find that unwatchable rather than moving.

Eighth Grade poster

The Perks of Being a Wallflower2012

Same energy: a socially estranged young person discovering there's warmth in the world if you stop judging it from behind a wall. Logan Lerman and Ezra Miller anchor the messy, genuine friendships.

But Emotionally manipulative in its own way. The manic pixie dream girl trope looms large.

The Perks of Being a Wallflower poster

Never Have I Ever2020

Mindy Kaling's series about a hyperintelligent Indian-American teen navigating sex, grief, and social survival. Devi Vishwanathan is difficult, funny, and allowed to grow.

But Teen melodrama can feel thin. Seasons later lose momentum, though the first is genuinely great.

Never Have I Ever poster

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The wildcard

Something you would not have found on your own.

Synecdoche, New York2008

Both centre on a brilliant person whose intellectual rigidity isolates them from life. Both suggest that connection requires you to lower your standards—not about people, but about perfection.

Charlie Kaufman's baroque masterpiece about a theatre director building a life-sized replica of Manhattan inside a warehouse. Disorienting, heartbreaking, genuinely weird. Philip Seymour Hoffman as a man collapsing into his own ambitions and ideas.

But Genuinely difficult to follow. Three hours, self-referential, deliberately opaque. Not entertainment, exactly—more an experience of drowning.

Synecdoche, New York poster
More like this (6)

Gilmore Girls2000

If you loved Carrie Pilby's witty isolation and rapid-fire dialogue, this is the ancestor. Rory and Lorelai's intellectual snobbery softens into real love.

But Deeply dated in places. Can feel static. The pacing and constant pop-culture jokes are not for everyone.

Gilmore Girls poster

Lady Bird2017

Greta Gerwig's film about a difficult teenager and her difficult mother, Sacramento-set, tender and specific. Saoirse Ronan is prickly and real.

But Slower and more introspective than Carrie Pilby. Less plot-driven, more emotional geography.

Lady Bird poster

10 Things I Hate About You1999

Kat Stratford (Julia Stiles) is the intellectual outsider who despises the world and everyone in it—until she doesn't. A teen movie that doesn't condescend to smart girls.

But A product of 1999. Some of the gender politics read dated now, though the lead character holds up.

10 Things I Hate About You poster

The Summer I Turned Pretty2022

A beach-set ensemble about growing up, choosing sides, and learning people are complicated. Lighter than Carrie Pilby but shares the same coming-of-age DNA.

But Young adult romance beats the character development. Many find it saccharine or predictable.

The Summer I Turned Pretty poster

Submarine2011

Richard Ayoade's debut: a misanthropic Welsh teenager convinced the world is beneath him must figure out how to actually live in it. British, funny, sad, precise.

But Very much a product of its era. The whimsy can feel forced. Some find the protagonist too detestable to follow.

Submarine poster

Chungking Express1994

A film about how ideas and the real world collide. Carrie Pilby's New York is dense with intellectual plans; this is about letting yourself be surprised instead.

Wong Kar-wai's neon-soaked Hong Kong love story, told in fragments and almost no plot. Two cops fall in love with women they barely know. Visually intoxicating, emotionally reckless, genuinely hopeful.

But Deliberately plot-light and impressionistic. In Mandarin and Cantonese with subtitles. The second half is almost plotless. Some find it beautiful, some find it precious.

Chungking Express poster

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