Sleeping with Other People Leslye Headland

Sleeping with Other People Leslye Headland
Courtesy of VVS Films
Romantic comedy writer-director Leslye Headland (Bachelorette, About Last Night) has done the impossible: made former SNL sweetheart Jason Sudeikis and charming Community star Alison Brie truly unlikeable — whether together or apart — in her new film, Sleeping with Other People.
Brie plays Lainey, a teacher living in bustling New York City who's in a somewhat committed relationship with her college crush Matthew (Adam Scott), a dick of a gynaecologist who is having an affair with her in the off hours away from his wife, who bumps into the man she lost her virginity to, Jake (Sudeikis, a local womanizer in his own right), after leaving a sex addicts anonymous meeting.
Their chance encounter decades after a one-night fling quickly turns into a hot-and-heavy friendship, one filled with casual dates over Chinese food, shopping excursions for big screen televisions, and even a safe word for when the sexual tension starts to get a little too high (mousetrap, which is undoubtedly the most awkward word choice in this script).
Think of it as a When Harry Met Sally… for the modern-day, Bushwick-residing hipster and you're getting close, but Headland has somehow managed to create a film that lacks any of the charm and poignancy of the former, while containing all the pessimism and twisted takes on the world of the latter. Jake and Lainey continually fall prey too easily to their past insecurities and emotional mishaps, and although it's always great to see such flawed adults navigating the minefield that is modern romance on the silver screen, there's something about these ones that just don't stick.
The Generation Y audience this film is aimed squarely at will surely find lots of familiar faces — including Amanda Peet, Natasha Lyonne and Adam Brody — and moments that may or not mirror their lives (taking ecstasy at a kid's birthday party, anyone?) to get them through the film's weaker moments, but it's hard not to feel like Headland has taken some tired tropes and made them even harder to stomach by injecting ample amounts of cynicism into a few too many scenes, even when what they discuss isn't depicted in enough mainstream movies like this one.