Film

Sleeping with Other People

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.

TMDb rating3.1

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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.

What's Your Number? poster

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.

The Good Place poster

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.

Trainwreck poster

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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.

C.R.A.Z.Y. poster
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.

Don't Trust the B---- in Apartment 23 poster

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.

Forgetting Sarah Marshall poster

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.

Love poster

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.

Someone Great poster

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.

Crazy, Stupid, Love. poster

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.

Paradise Hills poster

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.

The Cry of the Owl poster

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.

Marriage Story poster

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