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Movies Like Careless
Find movies like Careless (1993) using TMDB similarity plus Movie Rankings community context. Our top current pick is The Kissing Booth 2. Browse 18 related titles with direct links to rankings, cast pages, and matchup data.
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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.
The Broken Hearts Gallery
2020
Lucy is a young gallery assistant who collects mementos from her relationships. She discovers that she must let go of her past to move forward, and comes up with a lovely, artistic way to help herself and others who have suffered heartbreak.
Handsome Devil
2017
A music-mad 16-year-old outcast at a rugby-mad boarding school forms an unlikely friendship with his dashing new roommate.
Keith
2008
Natalie is high school royalty, but her queen bee status falls apart when she falls for the new guy at school. Although Keith ignores her at first, they soon become friends -- even though Natalie suspects that Keith has something to hide. As the free-spirited Keith shows Natalie how to embrace what life offers, they grow closer -- until a secret tests the bounds of their relationship
Puppy Love
2023
After a disastrous first date, wild-child Nicole and socially-anxious Max vow to lose each other’s numbers until they learn that their dogs found a love match, and now puppies are on the way! The hilariously mismatched Nicole and Max are forced to become responsible co-parents, but may end up finding love themselves.
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?
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.
My Sassy Girl
2008
A guy has his life planned out until he is wooed, groomed and then dumped by an elusive woman.
Secret Admirer
1985
An anonymous love letter left in Michael Ryan's locker on the last day of school wreaks havoc on his life and the lives of everyone who comes in contact with it.
Bridget Jones: Mad About the Boy
2025
Bridget Jones navigates life as a widow and single mum with the help of her family, friends, and former lover, Daniel. Back to work and on the apps, she's pursued by a younger man and maybe – just maybe – her son's science teacher.
The Lonely Guy
1984
A writer for a greeting card company learns the true meaning of loneliness when he comes home to find his girlfriend in bed with another man.
Sidelined: The QB and Me
2025
Dallas, a burdened but headstrong dancer, is determined to get into the best dance school in the country—her late mother’s alma mater. However, that dream is suddenly derailed when the cheeky yet secretly grieving football star, Drayton, crashes into her life with a unique story of his own. Will the two of them be able to grow into their dreams together, or will their dreams be sidelined?
Only the Lonely
1991
Danny Muldoon, a Chicago policeman, still lives with his overbearing mother Rose. He meets and falls in love with Theresa Luna, whose father owns the local funeral parlour. Naturally, his mother objects to the relationship, and Danny and Theresa must either overcome her objections or give up the romance.
St. Elmo's Fire
1985
Reluctant to let go of college life, a close-knit team of seven friends--irresponsible saxophone player Billy, young Republican Alec, his girlfriend Leslie, struggling journalist Kevin, drama queen Jules, lovesick waiter Kirby, and Wendy, a social worker with a heart of gold--realise the party is over. And as the burdens of maturity close in on the young dreamers, the complexities of adulthood and the daily struggle of growing up put their sacred friendship to the test. But everyone knows life is not a bed of roses. It won't be easy, but when all is said and done, what will it take for St. Elmo's clique to find its place in the real world?
Splendor
1999
Veronica is a white-bread beauty searching for a good man in Los Angeles. While slam dancing at a Halloween rave, she meets Abel, a sensitive poet. Then she meets Zed, a supersexy tattooed drummer with incredible biceps. Who will she choose? Does she go for true love or cheap sex? She can't decide so she chooses both. But after managing to nurture a picture-perfect threesome, along comes Ernest, a rich movie director with deep baby blues that sweep Veronica off her feet. What's a girl to do now?
John Tucker Must Die
2006
After discovering they are all dating the same same guy, three popular students from different cliques band together for revenge, so they enlist the help of a new gal in town and conspire to break the jerk's heart, while destroying his reputation.
Waiting for Forever
2010
A Hollywood-set romantic tale of a guy who is content to live his life without a job yet with the love of his life, a young actress.
The Break-Up
2006
Pushed to the breaking-up point after their latest 'why can't you do this one little thing for me?' argument, Brooke calls it quits with her boyfriend Gary. What follows is a hilarious series of remedies, war tactics, overtures and undermining tricks – all encouraged by the former couple's friends and confidantes …and the occasional total stranger! When neither ex is willing to move out of their shared apartment, the only solution is to continue living as hostile roommates until one of them reaches breaking point.
What are the best movies like Careless?
The Kissing Booth 2 is the strongest current recommendation on this page for viewers looking for movies like Careless.
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This page currently lists 18 related titles for Careless.
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