Spoilers for When Harry Met Sally and Sleeping with Other People.
When Harry Met Sally (1989), a now–classic film, has plenty of references to other classic love stories, from discussions of Casablanca (1942) to the Louis Armstrong and Ella Fitzgerald oldies on the soundtrack. Interspersed throughout are talking heads of elderly couples sharing their love stories, marking the pivotal points of Harry and Sally’s story. At first, the pair is positioned as complete opposites — Sally the high–maintenance optimist to Harry’s smarmy cynic — yet as their friendship develops, their vulnerabilities and compatibility gradually come to the fore, and the two prove endearing and funny in equal measure.
But first, some false starts. The film begins somewhat stereotypically, trapping Harry and Sally in a car driving from Chicago to New York. Their initial antagonism and the question they debate — Can men and women really be friends? — are just red herrings, however, that mock the forced antagonism of other rom–coms. The road trip that might have taken ninety minutes in another film is over within fifteen, and Harry and Sally separate with no expectation of meeting ever again.
Nevertheless, this is a rom–com and they are reunited twice more — during a flight five years later, picking up their disagreement right where they left off, and then a third time five more years later, after both have just exited serious relationships. This time, they go to lunch, unpacking their respective breakups and finally agreeing to be friends. Although both are getting over their exes and have no intention of dating, the film hints at what’s to come — the beginning of their friendship mimics Harry’s dating pattern that he described earlier, getting a “safe lunch” together before going to dinner, as the film’s theme, “It Had to Be You,” plays unobtrusively.
© Sam Valadi / CC BY 2.0
What follows is a montage, both morose and comedic, of the pair moving on from their breakups and wandering New York City together, while a phone call between them is heard in voiceover. The sequence ends with a split screen as they watch Casablanca on the same channel from their respective apartments. Although the contrast between Sally’s cheery bedroom and Harry’s dreary one reflect their differing personalities, the scene emphasizes their compatibility and connectedness. The couple spends much of the film seated across from one another at various outings, filmed in shot–reverse shot, but here they are side–by–side.
Although their determination to remain platonic complicates their eventual romantic feelings and delays their happy ending by a few months, Harry and Sally’s compatibility is underscored by their friendship. They are brutally honest and courageously vulnerable with one another, sharing details of their romantic trials and sex lives, including the iconic scene in which Sally fakes an orgasm in a diner to prove to Harry how easy it is. The film’s ultimate message has nothing to do with whether men and women can be just friends, instead demonstrating that the best relationships begin with friendship.
Sleeping with Other People (2015) has a very similar premise and structure, to the point that writer–director Leslye Headland described it as “‘When Harry Met Sally’ for assholes.”1 In it, Jake and Lainey, who lost their virginity to each other in college, reunite twelve years later after each has gone through a bad breakup. Both are serial cheaters who sabotage all of their relationships — Jake because he is cynical about love and too immature to just break up with his girlfriends; Lainey because she keeps going back to her neglectful recurring fling, Matt. Although it also asks whether men and women can be friends, the film is similarly disinterested in answering that question, but for different reasons.
Jake and Lainey admit to their mutual attraction very early on in the movie, but agree not to act on it, determined not to sabotage their nascent friendship. This accord is followed by a montage of the pair growing closer that mirrors that of When Harry Met Sally, including the split screen at the conversation’s end, the voiceover updated from a phone call to a text exchange. Yet while Lainey is shown getting over Matt, Jake continues his womanizing ways and the split screen of the last shot expands to fill the whole screen to show his departing one–night stand, out of frame while he spoke to Lainey.
Although Jake and Lainey have similar issues with commitment and even, it’s suggested, sex addiction, only Lainey is shown actually overcoming her problems, finally standing up for herself against Matt and applying to med school, a long–delayed ambition. Jake, by contrast, remains the same for much of the montage and the film, rarely opening up to Lainey, only to suddenly realize that he’s in love with her. Lainey reciprocates, but neither acts on their feelings — she’s moving to Michigan for med school and he’s afraid to ruin their friendship.
© Sofiamoreiralima / CC-BY-SA-4.0
Jake’s static character development is epitomized by the scene where he teaches Lainey how to masturbate, using a plastic bottle to demonstrate. Instead of mutually learning about relationships from each other, as Harry and Sally do, Jake instructs Lainey about relations with men and herself, placing himself in a position of mastery. He does not change so much as realize that Lainey is “the one,” a concept whose existence he spent his entire adulthood denying.
This is the one of the main differences between the two films. When Harry Met Sally is dominated by its leads and the growth they experience together. Rare is the scene that isn’t an intimate or important moment for the two, as they come to terms with their flaws and their love. Significantly, Harry and Sally watch their best friends Jess and Marie fall in love, an undeniable reminder to snatch up a compatible partner when you find them. In comparison, Sleeping with Other People distracts from its main romance with other flings and its secondary characters tell Jake and Lainey what their flaws are, instead of showing them. The movie is a little grittier, a little meaner — in its portrayal of its characters, the framing of New York’s streets, even in its EDM soundtrack and movie references (The Graduate (1967) and Misery (1990)). Although both films share a similar message — the importance of friendship as a foundation for love — and feature a happy ending, the former is a cleaner depiction, emotionally and filmically, while the latter isn’t afraid to show life’s messiness, even if it confuses the narrative.
1 Nick Allen. “Sleeping with Other People.” Review, September 11, 2015. https://www.rogerebert.com/reviews/sleeping-with-other-people-2015