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Movies Like Cupids

Find movies like Cupids using TMDB similarity plus Movie Rankings community context. Our top current pick is Crazy, Stupid, Love.. Browse 18 related titles with direct links to rankings, cast pages, and matchup data.

These picks blend TMDB similar-title seeds with Movie Rankings community ranking context.

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TMDB Recommended

Crazy, Stupid, Love.

Community rank #306 · 2011

Cal Weaver is living the American dream. He has a good job, a beautiful house, great children and a beautiful wife, named Emily. Cal's seemingly perfect life unravels, however, when he learns that Emily has been unfaithful and wants a divorce. Over 40 and suddenly single, Cal is adrift in the fickle world of dating. Enter, Jacob Palmer, a self-styled player who takes Cal under his wing and teaches him how to be a hit with the ladies.

TMDB Recommended

Sabrina

1954

After her return from school in Paris, a playboy finally takes notice of his family's chauffeur's daughter Sabrina, who's long had a crush on him, but he questions his more serious brother's motives when he warns against getting involved with her.

TMDB Recommended

Rushmore

1998

When a beautiful first-grade teacher arrives at a prep school, she soon attracts the attention of an ambitious teenager named Max, who quickly falls in love with her. Max turns to the father of two of his schoolmates for advice on how to woo the teacher. However, the situation soon gets complicated when Max's new friend becomes involved with her, setting the two pals against one another in a war for her attention.

TMDB Recommended

Clueless

1995

Shallow, rich and socially successful Cher is at the top of her Beverly Hills high school's pecking scale. Seeing herself as a matchmaker, Cher first coaxes two teachers into dating each other. Emboldened by her success, she decides to give hopelessly klutzy new student Tai a makeover. When Tai becomes more popular than she is, Cher realizes that her disapproving ex-stepbrother was right about how misguided she was -- and falls for him.

TMDB Recommended

The Edge of Seventeen

2016

Two high school girls are best friends until one dates the other's older brother, who is totally his sister's nemesis.

TMDB Recommended

People We Meet on Vacation

2026

Poppy's a free spirit. Alex loves a plan. After years of summer vacations, these polar-opposite pals wonder if they could be a perfect romantic match.

TMDB Recommended

After Ever Happy

2022

As a shocking truth about a couple's families emerges, the two lovers discover they are not so different from each other. Tessa is no longer the sweet, simple, good girl she was when she met Hardin — any more than he is the cruel, moody boy she fell so hard for.

TMDB Recommended

No Hard Feelings

2023

On the brink of losing her childhood home, Maddie discovers an intriguing job listing: wealthy helicopter parents looking for someone to “date” their introverted 19-year-old son, Percy, before he leaves for college. To her surprise, Maddie soon discovers the awkward Percy is no sure thing.

TMDB Recommended

Miss Stevens

2016

Stuck at a crossroads in her personal life, it falls on high school English teacher Miss Stevens to chaperone three of her students — Billy, Margot and Sam — on a weekend trip to a drama competition.

TMDB Recommended

Dutch

1991

To get to know his girlfriend's son, a man volunteers to pick him up from a prep school... only to learn that her son's not the nicest kid.

TMDB Recommended

Sex Drive

2008

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

TMDB Recommended

Summer School

1987

A high-school gym teacher has big plans for the summer, but is forced to cancel them to teach a "bonehead" English class for misfit goof-off students. Fortunately, his unconventional brand of teaching fun field trips begins to connect with them, and even inspires ardor in some.

TMDB Recommended

Kissing Jessica Stein

2002

Jessica, a Jewish copy editor living and working in New York City, is plagued by failed blind dates with men, and decides to answer a newspaper's personal advertisement. The advertisement has been placed by 'lesbian-curious' Helen Cooper, a thirtysomething art gallerist.

TMDB Recommended

Another Gay Movie

2006

Andy is your typical All-American eighteen-year-old gay virgin. Like everyone else, he's dying to have sex. Totally out of the closet and mad-crazy horny, this naïve high school senior is caught in that awkward vortex between child and adult. Much to the dismay of his mom (who wonders why all her carrots and cucumbers keep disappearing), Andy spends much of his private time practicing for the big moment when he'll finally take the plunge.

TMDB Recommended

Love, Weddings & Other Disasters

2020

A fussy celebrity caterer, a blind woman, a tour-bus guide and an inexperienced wedding planner search for love.

TMDB Recommended

Crossing Delancey

1988

Thirty-something Isabelle spends her time going from her tiny, solitary West Side apartment to that of her grandmother on the Lower East Side. While her grandmother plots to find her a romantic match, Isabelle is courted by a married, worldly author, Anton, yet can't seem to shake the down-to-earth appeal of Sam, a pickle vendor.

TMDB Recommended

Speech & Debate

2017

Frustrated by the hypocrisy they see in their parents, teachers, and the entire school board, an unlikely trio set out to find a common truth and make their voices heard as they revive a defunct school club and take on the world.

TMDB Recommended

Mr. Jealousy

1998

After his first date at age 15 ended with the girl making out with another man at a party, aspiring writer Lester Grimm has treated all his girlfriends with jealousy and suspicion. While dating Ramona Ray, paranoia gets the best of him when he discovers that her most recent ex is successful novelist Dashiell Frank. Lester begins attending the same group therapy sessions as Dashiell to learn about Ramona's past with him.

What are the best movies like Cupids?

Crazy, Stupid, Love. is the strongest current recommendation on this page for viewers looking for movies like Cupids.

How many recommendations are on the Cupids page?

This page currently lists 18 related titles for Cupids.

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This page refreshes whenever Movie Rankings rebuilds the related-title view for Cupids. It was last generated from site data on May 5, 2026.