Movies Like The Sure Thing
If you loved The Sure Thing's Comedy and Drama storytelling, these films deliver a similar experience — carefully selected for tone, themes, and emotional depth. Each pick includes where to watch it right now.
★ Top Picks
Sacramento
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
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
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.
Try Seventeen
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 Big Bold Beautiful Journey
Sarah and David are single strangers who meet at a mutual friend’s wedding and soon, through a surprising twist of fate, find themselves on a funny, fantastical, sweeping adventure together where they get to re-live important moments from their respective pasts, illuminating how they got to where they are in the present... and possibly getting a chance to alter their futures.
The Kissing Booth 2
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
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.
You Will Meet a Tall Dark Stranger
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.
More Movies Like The Sure Thing
Peace, Love & Misunderstanding
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.
Ana
Ana meets Rafa in a chance encounter and they embark on a road trip to try and save him from bankruptcy, or worse.
A California Christmas: City Lights
Follows Callie and Joseph one year after they fell in love, now running a dairy farm and winery, but their romance is threatened when business and family obligations call Joseph back to the city.
Peggy Sue Got Married
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.
American Graffiti
A couple of high school graduates spend one final night cruising the strip with their buddies before they go off to college.
Liberal Arts
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.
Reality Bites
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.
Chéri
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 Four Seasons
Three middle-aged wealthy couples take vacations together in Spring, Summer, Autumn and Winter. Along the way we are treated to mid-life, marital, parental and other crises.
Smart People
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.
The Mirror Has Two Faces
Rose Morgan, who still lives with her mother, is a professor of Romantic Literature who desperately longs for passion in her life. Gregory Larkin, a mathematics professor, has been burned by passionate relationships and longs for a sexless union based on friendship and respect.
Ezra
Stand-up comedian Max Bernal lives with his father Stan while struggling to co-parent his autistic son Ezra with his ex-wife. When forced to confront difficult decisions about their son's future, Max and Ezra embark on a cross-country road trip that has a transcendent impact on both their lives.
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)