Movies like The Sure Thing

After high school slacker Ferris Bueller successfully fakes an illness in order to skip school for the day, he goes on a series of adventures throughout Chicago with his girlfriend Sloane and best friend Cameron, all the while trying to outwit his wily school principal and fed-up sister.

Average student and eternal optimist Lloyd Dobler seeks to capture the heart of Diane Court, a beautiful but unattainable valedictorian classmate. He surprises just about everyone - including himself - when she returns the sentiment. However, Diane's divorced, over-protective father soon begins to disapprove of the match, and Lloyd realises that it's going to take more than just the power of love to conquer all.

Nerdy high schooler Ronald Miller rescues cheerleader Cindy Mancini from parental punishment after she accidentally destroys her mother's designer clothes. Ronald agrees to pay for the $1,000 outfit on one condition: that she will act as though they're a couple for an entire month. As the days pass, however, Cindy grows fond of Ronald, making him popular. But when Ronald's former best friend gets left behind, he realizes that social success isn't everything.

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.

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.

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

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.

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.

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.

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.

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.

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?