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Movies Like The Sure Thing (What to Watch After)

Looking for more content like The Sure Thing, you will appreciate how these films 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

Try Seventeen
6.2

Try Seventeen

2002

Teenager Jones has opted not to go to college and is instead renting a room in a boarding house to work on his writing skills. Soon, Jones finds himself dividing his time between two women: a young actress named Lisa and a photographer named Jane. After Jane's ex-boyfriend arrives to help her recover from a car accident, Jones begins to understand just how much he cares for her.

My Own Love Song
6.2

My Own Love Song

2010

A wheelchair-bound singer and her best friend embark on a roadtrip to Memphis.

Sacramento
6.2

Sacramento

2025

When free-spirited Rickey suddenly reappears in father-to-be Glenn’s life, the two former best friends embark on a spontaneous road trip from LA to Sacramento.

Grandma
6.5

Grandma

2015

Self-described misanthrope Elle Reid has her protective bubble burst when her 18-year-old granddaughter, Sage, shows up needing help. The two of them go on a day-long journey that causes Elle to come to terms with her past and Sage to confront her future.

Little Miss Sunshine
7.7

Little Miss Sunshine

2006

A family loaded with quirky, colorful characters piles into an old van and road trips to California for little Olive to compete in a beauty pageant.

Sex Drive
6.4

Sex Drive

2008

A high school senior drives cross-country with his best friends to hook up with a babe he met online.

The Kissing Booth 2
7.6

The Kissing Booth 2

2020

With college decisions looming, Elle juggles her long-distance romance with Noah, changing relationship with bestie Lee and feelings for a new classmate.

Licorice Pizza
7.0

Licorice Pizza

2021

The story of Gary Valentine and Alana Kane growing up, running around and going through the treacherous navigation of first love in the San Fernando Valley, 1973.

More Movies Like The Sure Thing

Peace, Love & Misunderstanding
5.8

Peace, Love & Misunderstanding

2011

A conservative lawyer named Diane takes her two teenage children Jake and Zoe to meet their estranged, hippie grandmother in Woodstock after her husband asks for a divorce.

You Will Meet a Tall Dark Stranger
5.9

You Will Meet a Tall Dark Stranger

2010

Two married couples find only trouble and heartache as their complicated lives unfold. After 40 years of marriage, Alfie leaves his wife to pursue what he thinks is happiness with a call girl. His wife, Helena, reeling from abandonment, decides to follow the advice of a psychic. Sally, the daughter of Alfie and Helena, is unhappy in her marriage and develops a crush on her boss, while her husband, Roy, falls for a woman engaged to be married.

Peggy Sue Got Married
6.1

Peggy Sue Got Married

1986

At her 25th high school reunion, Peggy Sue faints and awakens in 1960—back in her senior year, before her marriage and all her regrets. Given a second chance to relive her youth, she must decide whether to change the choices that shaped her life or embrace the past that made her who she is.

Ana
6.3

Ana

2020

Ana meets Rafa in a chance encounter and they embark on a road trip to try and save him from bankruptcy, or worse.

A Little Romance
6.8

A Little Romance

1979

Intellectually precocious teenager Lauren King lives in Paris with her somewhat ditzy mother. On a movie set, she strikes up a friendship with teenage film buff Daniel Michon. After Lauren's mother forbids her to date the outspoken Daniel, the young lovebirds team up with eccentric pickpocket Julius to run away to Venice, where, according to legend, a couple who kiss under the Bridge of Sighs will stay together forever.

American Graffiti
7.0

American Graffiti

1973

A couple of high school graduates spend one final night cruising the strip with their buddies before they go off to college.

Cherry
6.2

Cherry

2010

Ivy League Freshman, Aaron Milton (17) gets a different kind of education when he falls for Linda (34) a vivacious former wild-child who has returned to college to straighten out her life. The curriculum gets more challenging when Aaron meets Linda's sarcastic 14 year-old daughter, Beth - who quickly develops a crush on him. The math doesn't work in either direction but the dysfunctional triangle becomes a learning experience for all involved.

Reality Bites
6.6

Reality Bites

1994

A small circle of friends suffering from post-collegiate blues must confront the hard truth about life, love and the pursuit of gainful employment. As they struggle to map out survival guides for the future, the Gen-X quartet soon begins to realize that reality isn't all it's cracked up to be.

Liberal Arts
6.5

Liberal Arts

2012

Newly single, 35, and uninspired by his job, Jesse Fisher worries that his best days are behind him. But no matter how much he buries his head in a book, life keeps pulling Jesse back. When his favorite college professor invites him to campus to speak at his retirement dinner, Jesse jumps at the chance.

Chéri
6.1

Chéri

2009

The son of a courtesan retreats into a fantasy world after being forced to end his relationship with the older woman who educated him in the ways of love.

The Yellow Handkerchief
6.3

The Yellow Handkerchief

2009

A road trip through Louisiana transforms three strangers who were originally brought together by their respective feelings of loneliness.

Smart People
5.8

Smart People

2008

Professor Lawrence Wetherhold might be imperiously brilliant, monumentally self-possessed and an intellectual giant -- but when it comes to solving the conundrums of love and family, he's as downright flummoxed as the next guy.

Why These Movies Are Similar

These recommendations share core qualities with The Sure Thing (1985): Comedy and Drama 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 The Sure Thing.

See full details for The Sure Thing (1985)

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