Movies Like The Sure Thing

If you liked The Sure Thing (1985), a comedy and romance movie directed by Rob Reiner, here are 20 movies with a similar feel, based on TMDB's recommendations. Each one links to its cast, trailer and where it's streaming.

1
Sex Drive (2008)
★ 6.4/10Also comedy and romance
A high school senior drives cross-country with his best friends to hook up with a babe he met online.
2
Late Night Shopping (2001)
★ 6.4/10Also comedy and romance
Four friends Sean, Vincent, Lenny and Jody find themselves at something of a deadend. Trapped in a twilight world of permanent night shift work, they hang out together in the local cafe, drinking coffee and…
3
Playing It Cool (2014)
★ 5.9/10Also comedy and romance
A young man meets and instantly falls in love with an engaged woman.
4
¿Quieres ser mi hijo? (2023)
★ 8.4/10Also comedy and romance
Lu, a conformist woman in her forties, learns that her 15-year partner has been having extramarital affairs. Starting from scratch, she gets involved in an unexpected relationship with a young womanizer.
5
Splendor (1999)
★ 6.2/10Also comedy and romance
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…
6
Fanboys (2009)
★ 6.2/10Also comedy
In 1999, Star Wars fanatics take a cross-country trip to George Lucas' Skywalker Ranch so their dying friend can see a screening of The Phantom Menace before its release.
7
Jackass Presents: Bad Grandpa (2013)
★ 6.2/10Also comedy
86-year-old Irving Zisman is on a journey across America with the most unlikely companion: his 8 year-old grandson, Billy.
8
A Nice Girl Like You (2020)
★ 5.8/10Also comedy and romance
Lucy Neal is thrown for a loop when she is accused of being too inhibited by her ex-boyfriend. In an effort to prove him wrong, Lucy creates a rather wild to-do list that sends her on a whirlwind and surprising journey…
9
The Last Summer (2019)
★ 6/10Also romance and comedy
Standing on the precipice of adulthood, a group of friends navigate new relationships, while reexamining others, during their final summer before college.
10
Sex Appeal (2022)
★ 6.6/10Also comedy and romance
Avery, a teenager with a tendency towards perfectionism, enlists her friend Larson to help her prepare for her first time with her long-distance boyfriend.
11
Mr. Jealousy (1998)
★ 5.9/10Also comedy and romance
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…
12
A Midsummer Night's Sex Comedy (1982)
★ 6.5/10Also comedy and romance
A nutty inventor, his frustrated wife, a philosopher cousin, his much younger fiancée, a randy doctor, and a free-thinking nurse spend a summer weekend in and around a stunning - and possibly magical - country house.
13
Puppy Love (2023)
★ 7/10Also comedy and romance
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…
14
Sundown (2016)
★ 5.8/10Also romance and comedy
High school seniors Logan and Blake prepare for an epic Spring Break as they travel to the beautiful and exotic Mexican beach resort of Puerto Vallarta hoping to hook up with their high school crushes. Surrounded by…
15
Road Trip (2000)
★ 6.3/10Also comedy
After a student at the University of Ithaca films his one-night stand with a beautiful sorority girl, he discovers one of his friends has accidentally mailed the homemade sex tape to his girlfriend in Austin. In a…
16
Neighbors 2: Sorority Rising (2016)
★ 5.8/10Also comedy
A sorority moves in next door to the home of Mac and Kelly Radner who have a young child. The Radner's enlist their former nemeses from the fraternity to help battle the raucous sisters.
17
No Hard Feelings (2023)
★ 6.7/10Also comedy and romance
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…
18
Players (2024)
★ 6/10Also romance and comedy
New York sportswriter Mack has spent years devising successful hook-up "plays" with her friends, but when she unexpectedly falls for one of her targets, she must learn what it takes to go from simply scoring to playing…
19
Love in the Villa (2022)
★ 6/10Also romance and comedy
A young woman takes a trip to romantic Verona, Italy, after a breakup, only to find that the villa she reserved was double-booked, and she'll have to share her vacation with a cynical British man.
20
Palm Springs (2020)
★ 7.3/10Also comedy and romance
When carefree Nyles and reluctant maid of honor Sarah have a chance encounter at a Palm Springs wedding, things get complicated when they find themselves unable to escape the venue, themselves, or each other.