
The Sure Thing
Gib, a beer-guzzling slob, and Alison, an uptight Ivy-Leaguer, are an unlikely duo stuck together on a cross-country trip during Christmas break. At first they get on each other's nerves but, as time passes, they find their divergent natures complement each other. Now they need to realize what they've already found before it's too late.
Movies Like The Sure Thing
Similar in style, tone, and themes — find your next watch.

Try Seventeen
2002★ 6.2
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.

Sex Drive
2008★ 6.4
A high school senior drives cross-country with his best friends to hook up with a babe he met online.

Sacramento
2025★ 6.3
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
2015★ 6.5
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.

Peggy Sue Got Married
1986★ 6.1
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.

Cherry
2010★ 6.2
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.

Smart People
2008★ 5.8
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.

Kodachrome
2017★ 6.8
Matt Ryder is convinced to drive his estranged and dying father Benjamin Ryder cross country to deliver four old rolls of Kodachrome film to the last lab in the world that can develop them before it shuts down for good. Along with Ben's nurse Zooey, the three navigate a world changing from analogue to digital while trying to put the past behind them.

Sideways
2004★ 7.1
Two middle-aged men embark on a spiritual journey through Californian wine country. One is an unpublished novelist suffering from depression, and the other is only days away from walking down the aisle.

ATL
2006★ 6.9
As four friends prepare for life after high school, different challenges bring about turning points in each of their lives. The dramas unfold and resolve at their local rollerskating rink, Cascade.

Scarecrow
1973★ 7.1
Two drifters bum around, visit earthy women and discuss opening a car wash in Pittsburgh.

Strictly Sexual
2008★ 6.1
Two successful women, sick and tired of dating and relationships, decide to keep two young men in their pool house for strictly sexual purposes.

Chéri
2009★ 6.1
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.

Winter Spring Summer or Fall
2024★ 7.2
Remi and Barnes, two very different teenagers, meet by chance in the winter of their senior year, then spend four days together over the course of a year that will change their lives forever.

St. Elmo's Fire
1985★ 6.1
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?

The Last Summer
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Standing on the precipice of adulthood, a group of friends navigate new relationships, while reexamining others, during their final summer before college.

Irreplaceable You
2018★ 6.9
A stunning cancer diagnosis spurs Abbie to seek a future girlfriend for fiancé and childhood sweetheart Sam, who's clueless when it comes to dating.

About Alex
2014★ 6.1
When a group of old college friends reunite over a long weekend after one of them attempts suicide, old crushes and resentments shine light on their life decisions, and ultimately push friendships and relationships to the brink.

Wristcutters: A Love Story
2007★ 7.0
Zia, distraught over breaking up with his girlfriend, decides to end it all. Unfortunately, he discovers that there is no real ending, only a run-down afterlife that is strikingly similar to his old one, just a bit worse. Discovering that his ex-girlfriend has also "offed" herself, he sets out on a road trip to find her.

Young People Fucking
2007★ 5.8
On a Tuesday night, five couples have separate sexual adventures. Matt and Kris, friends for years, want to have an only-once, no-strings good time. Abby and Andrew, married, celebrate his birthday, but it's marred by angst and miscommunication. Mia and Eric are exes, making sure they are over each other. Jaime and Ken work together and this is a first date. Inez and Gord invite his roommate, Dave, to join them. By the time each couple has gone through a prelude, foreplay, sex, an interlude, orgasm, and afterglow, they've answered basic questions: can sex be anonymous, are we bored, is our marriage really finished, does anyone tell the truth, and how do we make someone happy?