Sleeping With Other People

IFC Films, 2015
Writer: Leslye Headland
Director: Leslye Headland
Out of 5: 4.5

To Leslye Headland, it must feel like she’s been hit by a Judd Apatow hex with her film career. Her 2012 debut, Bacherlorette, was overshadowed by the previous year’s Apatow-produced Bridesmaids. The only real commonality between the two films was brides behaving badly, with Headland telling a far more darker and slightly tougher-to-embrace film that, nevertheless, told a more interesting story and was filled with bitterly comedic dialogue. Now this year, Headland’s sophomore film, Sleeping With Other People, comes out in the shadow of Trainwreck, an Apatow-directed film that also deals in part with more sexually voracious characters than normally depicted in romantic comedies. Headland’s tone has sweetened a bit more this time around, but her film is no less sharp than the Apatow echo, and the film explores a more interesting, better-developed relationship than is normally seen in rom-coms.

This unique relationship come from the circumstances that the main couple Greg (Jason Sudeikis) and Lainey (Alison Brie) find themselves in. After losing their virginity to each other in college, the duo are reconnected at the same sex addiction support group several years later and with far more emotional baggage between them. Greg just hasn’t found the right person for him, so every time he hits a stumbling block in a relationship, he turns to sex with a new hot girl. Lainey’s problem is that, no matter what relationship she finds herself in, she just can’t stop the desire for college crush turned gynecologist Matthew (Adam Scott at his sleaziest). Because both Greg and Lainey are aware of how messed up their lives are, they decide that they can only be friends with each other. But will the undeniable chemistry between them soon lead to a more than friendly relationship?

While the film ends up in a familiar place by the end, the way the film gets there makes the ending far more enjoyable than it would otherwise be. In making the couple not a couple for the vast majority of the film, Sudeikis and Brie are able to bring their considerable charms without feeling like a misunderstanding or argument will temporarily destroy this relationship, like so many other romantic comedies resort to in their third act. Sudeikis is perfect here in his usual film persona: a horndog who has enough wit and intelligence to make it understandable why a woman could be attracted to him. Meanwhile, Brie brings the devilishness masquerading as innocence she brought to Community so well.

Beyond the strong central relationship, Sleeping With Other People just completely kills with the comedy portion of the romantic comedy. Leslye Headland is an immensely talented writer who has an ability to write exchanges with screwball comedy timing and considerably more explicit raunch than screwball comedy could dive into. The story and script riff off of the movie which first mastered the modern-day romantic comedy, When Harry Met Sally, complete with its own particularly memorable scene involving female pleasure. The film also shines whenever it brings in Sudeikis’ buddy, played by Jason Mantzoukas, who plays his usual off-kilter character that you might have seen in The League or the How Did This Get Made? podcast, but is a joy to see and hear every time.

While Trainwreck was enjoyable, it still suffered from the usual Apatow bloat and having a core romantic relationship not altogether that different from much of Apatow’s other films, only with the genders switched. It would be a shame for Sleeping with Other People, which doesn’t have those problems, to once more be overlooked for the hilarious pleasure that it is. Here’s hoping that third time’s the charm for Headland emerging from other comedies’ shadows.

Scott Goldfarb is a dedicated student of the arts, trying to learn more every day.