Film
Sleeping with Other People
- Romantic comedy
- Light-hearted
Two serial cheaters reconnect after twelve years and swear off each other to break their patterns. It's warm and funny without being cynical, genuinely interested in whether people can change and what intimacy means beyond sex. For anyone who's enjoyed a smart romantic comedy that trusts its audience to laugh at messy, flawed people without punishing them for it.
If you liked this
What's Your Number?2011
Charming rom-com about a woman cataloging her exes, it has the same energy of attractive people being ridiculous together. Anna Faris and Chris Evans have genuine chemistry, and the film never takes itself seriously enough to become saccharine.
But The premise is pretty thin, and it relies heavily on broad comedy that doesn't always land. If you need plot momentum, you might find it meandering.

The Good Place2016
A show about flawed people trying to be better, with Kristen Bell and Ted Danson. Witty, philosophical, and genuinely moving about whether change is possible—it's got that same warmth under the chaos.
But It takes a while to find its footing in season one, and the central premise shifts in ways some find either genius or frustrating. Requires patience.

Trainwreck2015
Amy Schumer plays a commitment-phobic woman who slowly learns connection matters. Directed by Judd Apatow with real emotional stakes beneath the jokes, and Bill Burr steals every scene he's in.
But Schumer's brand of humor is divisive, and the film occasionally veers into preachiness about self-improvement. Some find the tonal shifts awkward.

Not sure tonight? Get a pick in a minute, starting from Sleeping with Other People
The wildcard
Something you would not have found on your own.
C.R.A.Z.Y.2005
Both explore whether people can fundamentally change and whether love survives incompatibility. Both are about the mess between who you are and who you're trying to be.
A French-Canadian epic about a gay man and his complicated journey with his family across four decades. It's both hilarious and devastating, with the same underlying question as the film—how do you stay true to yourself while loving people who might not understand?
But It's in French, and at 127 minutes it's a full commitment. The tone shifts dramatically and unironically, which requires patience; there's no safety net of consistent comedy.

More like this (8)
Don't Trust the B---- in Apartment 232012
Rapid-fire comedies about two women who shouldn't work as friends but do. It's cynical about romance without being mean, and every episode crackles with invention. James Van Der Beek playing himself is inspired casting.
But Only ran two seasons before cancellation, so there's a limited supply. The humor is relentless—if you need moments to breathe, it might exhaust you.

Forgetting Sarah Marshall2008
A breakup comedy with real kindness at its core. Jason Segel and Kristen Bell have wonderful chemistry, and it manages to be both genuinely funny and surprisingly touching about hurt and moving on.
But Relies on some dated joke structures, and if you're not in the mood for mid-2000s comedy sensibility, it might feel thin. The humor is broad.

Love2016
Judd Apatow's series about two people figuring out if they work together, with Gillian Jacobs and Paul Rust. Messy, sometimes uncomfortable, but honest about how relationships actually feel—the mundane parts matter as much as the grand gestures.
But It's deliberately unglamorous and sometimes tedious in that realness. Some viewers find the characters too self-absorbed or the pacing too meandering to engage with.

Someone Great2019
Gina Rodriguez and a group of women go on one last trip before a major life change. It's funny and touching about female friendship, and it treats its characters with genuine affection even when they're being ridiculous.
But The emotional payoff requires you to care about the relationships, and if the buddy-comedy rhythm doesn't grab you early, the later sentiment might feel unearned.

Crazy, Stupid, Love.2011
An ensemble romantic comedy that actually earns its sentiment. Steve Carell, Ryan Gosling, and Emma Stone spark off each other, and the script is smarter than the premise suggests—it's about vulnerability, not perfection.
But It's neatly wrapped up in ways that feel a bit conventional. If you want messier, more complicated resolutions, this will feel tidy by comparison.

Paradise Hills2019
Anna Brody, Danielle Macdonald, and Michelle Monaghan escape a suspicious finishing school. It's gorgeously shot, strange, and genuinely funny in unexpected ways—a comfort watch for people who like weirdness baked into their entertainment.
But The plot is deliberately obscure and dreamlike, which frustrates viewers who want clear answers. It's more vibe than story.

The Cry of the Owl2009
Both wrestle with obsession and the difference between watching someone and truly knowing them. Both ask what happens when attraction without consent becomes part of the story.
A strange, tense psychological drama where Robert Redford's character becomes obsessed with observing a woman's life. Shot like a thriller but powered by emotional dread rather than plot. Hypnotic and deeply uncomfortable in the best way.
But It's glacially paced and the 'plot' is deliberately minimal. If you need momentum or clear stakes, you'll find it maddening. It's more about mood than narrative satisfaction.

Marriage Story2019
Both center on people who recognize their own capacity for harm in relationships and wonder if they deserve another try. Both are about whether self-awareness can change behavior, or if it's just another form of avoidance.
An unflinching look at two people who love each other while their relationship falls apart. Adam Driver and Scarlett Johansson are extraordinary, the dialogue is precise and brutal, and it's about the gap between who we want to be and who we are in relationships.
But It's devastatingly sad and often angry. There are no easy answers or comforting moments, just rawness. If you need your relationships on screen to resolve neatly, this will be difficult.

People
Cast
Jason SudeikisJake Harper
Alison BrieLainey Dalton
Adam ScottMatthew Sobvechik
Jason MantzoukasXander
Natasha LyonneKara
Adam BrodySam
Amanda PeetPaula
Marc BlucasChris Smith
Margarita LevievaHannah
Andrea SavageNaomi
Daniella PinedaDanica
Directing
- Leslye HeadlandDirector
Writing
- Leslye HeadlandScreenplay
Production
- Emer O'CallaghanCasting
- Jennifer EustonCasting
- Leslye HeadlandCo-Executive Producer
- Dylan TarasonCo-Producer
- Kathryn DeanCo-Producer
- Mark MikutowiczCo-Producer
- Bruce TollExecutive Producer
- Carla HackenExecutive Producer
- Jim TauberExecutive Producer
- Matt BerensonExecutive Producer
- Adam McKayProducer
- Jessica ElbaumProducer
- Sidney KimmelProducer
- Will FerrellProducer
- Franses SimonovichProduction Supervisor
- Kathryn DeanUnit Production Manager
Recommended by
When We First Met, The Little Death, Romantic Comedy, What's Your Number?, In a Relationship