'%20x='0'%20y='0'%20height='100%25'%20width='100%25'%20%0A%20%20%20%20%20%20%20%20%20%20xlink%3Ahref='data:image/jpg;base64,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'%3E%3C/image%3E%3C/svg%3E)
The Heartbreak Kid is a 2007 romantic comedy film. Ben Stiller plays Eddie Cantrow, a single guy in his forties who hurries into marriage with the apparently ideal Lila, played by Malin Akerman. But things change drastically during their honeymoon in Mexico when Eddie meets another lady and starts to doubt he might have made a big mistake.
The movie explores emotional concerns, including commitment, and incompatibility.
Many more romantic comedies provide a similar mix of fun, discomfort, and unexpected emotion for people who like the way the film combined laughter with uncomfortable love tales.
Not Another Teen Movie, She's Out of My League, and more romantic comedies similar to The Heartbreak Kid
1) Not Another Teen Movie (2001)
Trending
Not Another Teen Movie is a chaotic, self-aware romp through the absurdities of high school movie clichés. Directed by Joel Gallen, the film parodies every teen rom-com trope from the '80s and '90s, mashing together plotlines from She’s All That, 10 Things I Hate About You, Pretty in Pink, and Varsity Blues.
At the heart of the chaos is Jake Wyler (Chris Evans), a textbook jock who accepts a bet to turn nerdy Janey Briggs (Chyler Leigh) into a prom queen.
Despite its satirical tone, Not Another Teen Movie actually shares some DNA with raunchy rom-coms like The Heartbreak Kid.
Both lean into uncomfortable cringe and boundary-pushing comedy, never shying away from a ridiculous plot twist or exaggerated character.
Evans delivers early-career comedic brilliance, navigating the madness with perfect deadpan timing and exaggerated confidence.
Where to watch: Netflix, Apple TV
2) She's Out of My League
In She's Out of My League, Jay Baruchel plays Kirk, an awkward TSA agent. He goes on a date with Molly, played by Alice Eve. Molly is stunning and successful, and she seems out of Kirk's league.
Like The Heartbreak Kid, the humor in this film stems from misaligned expectations. These expectations cause anxiety and discomfort.
Much of the film's comedy comes from Kirk's disbelief in his own worth. On the surface, their relationship appears perfect.
However, underlying issues and uncertainty emerge. These themes reflect self-sabotage and vulnerability.
The film wraps these ideas into a surprisingly charming love story. It makes audiences laugh with its embarrassing situations and bad advice.
Where to watch: Netflix
3) Just Go With It (2011)
Just Go With It follows Adam Sandler as Danny, a plastic surgeon who pretends to be unhappily married to avoid serious relationships.
His lie goes out of hand when he meets Palmer, a woman he actually likes—forcing his assistant Katherine (Jennifer Aniston) to pass for his soon-to-be ex-wife.
Her children joining the ruse just makes things more messy; they all wind up on a wild trip to Hawaii.
The fundamental idea of both movies is the romantic complexity resulting from attempts to create love via dishonesty.
Just Go With It is a feel-good romantic comedy with tropical escapades, awkward meetings, and emotional curveballs.
It shows how occasionally faking may lead to something real, just not without a few wounded egos, outrageous admissions, and one big confrontation at a resort luau.
Where to watch: Netflix, Amazon Prime Video
4) The Holiday (2006)
While The Heartbreak Kid tackles love gone wrong with chaotic hilarity, The Holiday offers a softer, soul-soothing story about heartbreak, healing, and second chances.
Iris (Kate Winslet) and Amanda (Cameron Diaz) are both nursing emotional wounds when they impulsively swap homes—one in snowy Surrey, the other in sunny LA.
What starts as escapism turns into something far more meaningful: a chance to rediscover themselves and open up to love again.
This film focuses more on the quiet, healing moments between heartbreak and hope, rather than on humorous mishaps.
With charming performances from Jude Law and Jack Black, The Holiday trades in outrageous antics for emotional honesty, cozy atmospheres, and real connection.
It’s the perfect watch if you loved The Heartbreak Kid’s themes of romantic recklessness but are now ready for something a little more grown-up, a little more heartwarming—and just as satisfying.
Where to watch: Netflix, Amazon Prime Video
5) Set It Up (2018)
In Set It Up, Harper (Zoey Deutch) and Charlie (Glen Powell), two frazzled assistants, devise a plan to deceive their demanding bosses and finally find some relief.
But in their efforts to play Cupid, they find themselves entangled in their own unexpected romance.
Like The Heartbreak Kid, this rom-com thrives on well-meaning deception and the chaos that ensues when relationships don’t go according to plan.
But instead of cringeworthy mishaps and mismatched marriages, Set It Up offers sharp banter, New York charm, and a modern twist on the classic "will-they-won't-they."
While the stakes are lower, the emotional payoff is sweeter, and the chemistry between the leads is magnetic. Set It Up offers heart, humor, and a reminder that sometimes the best love stories begin with a clever plan that goes awry.
Where to watch: Netflix, Amazon Prime Video
6) Crazy, Stupid, Love (2011)
Crazy, Stupid, Love mirrors The Heartbreak Kid's depiction of the turmoil of hastily entering marriage life. explores the messiness that follows when one falls out of love, or thinks they have.
Steve Carell plays Cal, a newly single dad blindsided by divorce, who gets a suave life makeover from womanizer Jacob (Ryan Gosling).
Both films examine the comedic fallout of romantic reinvention, but where The Heartbreak Kid leans into cringe and impulsivity, Crazy, Stupid, Love. balances drama and humor with a web of interlocking love stories.
A brilliant twist in the third act ties everything together with emotional payoff, elevating it beyond a mere glossy rom-com.
With a stellar ensemble with Emma Stone and Julianne Moore, and a warm message about second chances, this one’s a clever, more mature companion to The Heartbreak Kid’s reckless romance.
Where to watch: Apple TV, Netflix
7) I Love You, Man (2009)
Marriage may be the goal, but I Love You, Man takes a hilarious detour into the awkward world of bromance. Paul Rudd stars as Peter, a groom-to-be who realizes he has no male friends close enough to stand beside him at the altar.
Enter Jason Segel’s Sydney—eccentric, unfiltered, and everything Peter didn’t know he needed in a best friend.
Like The Heartbreak Kid, this film thrives on uncomfortable humor and social faux pas. But instead of fixating on romantic misfires, it focuses on the emotional (and often ridiculous) dynamics of male friendship in adulthood.
Both movies extract humor from relational tension, but I Love You, Man conveys its emotional core through bro-bonding montages, awkward toasts, and a sincere affection for its characters.
It’s a romantic comedy where the central love story isn’t about the bride and groom—it’s about two guys finding friendship in the most unlikely of places.
Where to watch: Netflix, HBO Max, Apple TV
Meanwhile, The Heartbreak Kid is available for online streaming on Netflix.
