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Movies Like Dean

Fans of Dean, will enjoy these picks that questions the purpose and weight of our choices while delivering targets the intellect with complex, multi-layered ideas. Carefully balances character depth with narrative flow makes this definitely worth a watch.

Mood Breakdown
Runtime Cluster

Standard feature-length experiences.

Viewer Fit

Best for fans of who appreciate concise storytelling.

Top Picks

Sidewalks of New York
6.0

Sidewalks of New York

2001

The film follows the marital and dating lives of three men and three women who unknowingly form a tangled web of relationships. Interspersing "man on the street" interviews with scenes from the six characters' lives, the film weaves a humorous and biting commentary on the game of love -- easy to start, hard to finish.

The Incredible Jessica James
6.2

The Incredible Jessica James

2017

Burned by a bad breakup, a struggling New York City playwright makes an unlikely connection with a divorced app designer she meets on a blind date.

¿Quieres ser mi hijo?
8.5

¿Quieres ser mi hijo?

2023

Lu, a conformist woman in her forties, learns that her 15-year partner has been having extramarital affairs. Starting from scratch, she gets involved in an unexpected relationship with a young womanizer.

Bye Bye Love
5.9

Bye Bye Love

1995

With varying degrees of success, recently divorced friends Dave, Vic and Donny are trying to move on with their lives. Vic feels vilified by his ex-wife's parents, while Donny has a shaky bond with his teen daughter, Emma. Dave, meanwhile, has an enviable problem -- he has more dates than he can handle. As they confront their post-marital challenges, the men take solace in one another's plights.

The Wrong Paris
6.7

The Wrong Paris

2025

Dawn thinks she's joining a dating show in Paris, France, only to land in Paris, Texas. She has an exit plan — until sparks fly with the cowboy bachelor.

Cosi
6.1

Cosi

1996

Lewis, a young amateur theater director, is offered a job with a governmental program for the rehabilitation of mentally ill patients in a Sydney institution. His project is overrun by one of the patients, who wants to stage the opera Cosi Fan Tutte by Mozart, despite the fact that none of the patients can sing or speak Italian. A comedy of errors ensues, but one which unifies the patients and their director in unexpected ways.

Players
6.1

Players

2024

New York sportswriter Mack has spent years devising successful hook-up "plays" with her friends, but when she unexpectedly falls for one of her targets, she must learn what it takes to go from simply scoring to playing for keeps.

Which Brings Me to You
6.2

Which Brings Me to You

2023

Two romantic burnouts, Jane and Will, are immediately drawn to each other at a mutual friend’s wedding. After a disastrous hookup in the coatroom, the two spend the next 24 hours together, trading candid confessions of messy histories and heartbreak, on the off chance that this fling might be the real thing.

More Movies Like Dean

(Untitled)
6.4

(Untitled)

2009

A fashionable contemporary art gallerist in Chelsea, New York falls for a brooding new music composer in this comic satire of the state of contemporary art.

Prom Pact
7.2

Prom Pact

2023

It's prom season, and high school senior Mandy and her best friend and fellow outsider Ben are surrounded by over-the-top "promposals." Mandy is only focused on getting into her dream school Harvard, but as she starts tutoring basketball all-star Graham, she must re-evaluate whether her dream school is worth the cost of everything she believes in.

Rosaline
7.1

Rosaline

2022

Left heartbroken after Romeo begins to pursue her cousin Juliet, Rosaline schemes to foil the famous romance and win back her guy in this comedic twist of Shakespeare's Romeo and Juliet.

The Best You Can
7.0

The Best You Can

2025

Cynthia Rand is a buttoned-up New Yorker married to a brilliant professor 25 years her senior. She begins feeling the effects of her husband’s advancing age on their relationship, just as her world is turned upside down by the arrival of sharp but chronically underachieving security guard Stan Olszewski in this smart rom-com that reunites Bacon and Sedgwick on screen for the first time in 20 years.

Chasing Papi
6.7

Chasing Papi

2003

Playboy Thomas Fuentes has so far been able to skate by in life on good looks and charm alone. But when his duplicitous relationships with three women -- impassioned waitress Cici, meticulous lawyer Lorena and bored socialite Patricia -- spiral out of control, he suffers a mental breakdown. His doctor recommends that he choose just one girlfriend -- but can he choose in time before they discover his deception?

Jack Goes Boating
6.0

Jack Goes Boating

2010

A limo driver's blind date sparks a tale of love, betrayal, friendship and grace—centered on two working-class New York City couples.

How I Got Into College
5.9

How I Got Into College

1989

High school senior Marlon Bowne is smitten with overachieving classmate Jessica Kailo. But, if he wants to have a shot with her, he'll have to find a way to get into Ramsey College, Jessica's top choice of schools. It won't be easy, since the college is highly selective and Marlon's grades are hardly impressive. That means the lovelorn teen will have to find a way to score high on the SATs and win over the college admissions committee.

He Said, She Said
5.8

He Said, She Said

1991

Womanising, right-wing Dan Hanson and quiet, liberal Lorie Bryer work for the Baltimore Sun. Rivals for the job of new writer of a vacant column, the paper ends up instead printing their very different opinions alongside each other, which leads to a similarly combative local TV show. At the same time their initial indifference to each other looks like it may evolve into something more romantic.

We Broke Up
5.9

We Broke Up

2021

Lori and Doug break up right before Lori's sister's wedding and decide to pretend they're still together for the weekend as to not disrupt the fun.

A Nice Girl Like You
5.9

A Nice Girl Like You

2020

Lucy Neal is thrown for a loop when she is accused of being too inhibited by her ex-boyfriend. In an effort to prove him wrong, Lucy creates a rather wild to-do list that sends her on a whirlwind and surprising journey of self-discovery, friendship, and new love.

My Sassy Girl
6.7

My Sassy Girl

2008

A guy has his life planned out until he is wooed, groomed and then dumped by an elusive woman.

Catch and Release
5.9

Catch and Release

2006

For a grieving fiancée, learning to love again requires the help of her late love's three best friends.

Why These Movies Are Similar

These recommendations share core qualities with Dean (2016): Romance and Comedy themes, similar narrative structure, and comparable emotional depth. NoBadPicks uses a combination of TMDB collaborative filtering, genre matching, and AI analysis to surface films most likely to resonate with fans of Dean.

See full details for Dean (2016)

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