When Harry Met Sally is a fantastic movie, and as a romantic comedy, it’s groundbreaking in many ways. It’s got a fairly cynical viewpoint that delves into all the ways that tropes from other rom-coms just aren’t true. But it’s also got a quiet conservatism to it: it famously asks the question “can men and women just be friends,” and seems to answer “no.” Its main character is a stubborn, selfish, “human affront to all women,” and he also just so happens to be right about pretty much everything. It’s a movie that tears down our puffed-up ideas about how men and women should treat one another and tells us the way we do treat each other, the way we always have.
We’re not arguing that this movie, nor the older audiences who tend to prefer it, are somehow misogynist — it was written by the great Nora Ephron, for God’s sake! But we should also remember that the Baby Boomers who love it come of age during the “free love” movement, which sought to separate romantic love from sexual gratification and liberate people from repressive romantic norms. This movie was released in the middle of a backlash against the idealism of that movement, and in many ways, it exemplifies that backlash. Billy Crystal’s character believes men and women can’t be friends because sex and love can’t be separated, our actions have consequences, and people have fundamental differences that even the purest form of “true love” can’t reconcile. It’s no mystery why a generation old enough to have outgrown most of its delusions about romance would favor that message over a more optimistic one.