Jake (Sudeikis) and Lainey (Brie) lost their virginity to each other in a chance encounter in college and then lost contact. After more than a decade, they see each other again at a sex-addicts meeting, each with a different reason for being there. Lainey can't stop returning to the same average sex with a man she shouldn't be seeing because of how raunchy it is to fuck on an office desk, and Brie delivers her with the perfect amount of tragedy and sexiness. Jake doesn't know how to break up with women, so he just fucks their sister or best friend, and somehow Sudeikis performs just enough here despite his over-the-top-ness. They play the best friends who eventually fall into the "men and women can't just be friends!" trope, but watching their friendship is still really delightful. Watching them eat Ben n Jerry's pints together, frequent the same dingy Chinese restaurant, and take ecstasy at a child's birthday party feels intimate and truly modern when it comes to social media's #RelationshipGoals these days.
And where Sleeping With Other People really excels is how strong it is in both the "romance" and "comedy" subgenres. It's not afraid to be raunchy and takes it's time in sex scenes, even allowing us a peek at the gorgeous Brie in lingerie. There's a full scene where Jake teaches Lainey how to masturbate that emphasizes how confident the movie is at mixing sexy with humor. The comedy relies on writing that is barely cheesy and moreso intelligent, which is refreshing. There's clever references to The Graduate and the main characters are Columbia graduates who aren't afraid to let their conversations dissolve into philosophical banter. Where most of the movie has fun adeptly twisting genre expectations, the end of the movie drags out into an inevitable "happily ever after" ending. The tone gets thrown off and the conversations start to feel menial, but supporting characters like Xander (The League's Jason Mantzoukas) and Paula (The Whole Nine Yards's Amanda Peet) keep the movie afloat with their sarcastic tales of being married.
Aside from fulfilling my dreams of having Alison Brie and Katherine Waterston in one movie, Sleeping With Other People is an assured and adorable watch. The recognizable fear of honesty paired with the charismatic duo of Brie and Sudeikis is similar to the winning combination that makes up FX's You're the Worst. With romance in media these days, it's not about a couple in love but the unease leading up to the relationship. Sleeping With Other People nails that, and though it succumbs to a genre cliche ending, it's gratifying to see two flawed humans in perfect harmony.