The start of a season signifies a new beginning, and I often find myself offsetting change with a return to something familiar. Over a year after I first watched it, I decided to give When Harry Met Sally a second chance, needing to understand what has made it so comforting—especially around autumn—to viewers over the 34 years since its release.
When I watched When Harry Met Sally (1989) last summer, I followed my solo-screening with a shaken-up, half-infuriated Letterboxd review: “good until he straight up took advantage of her. right?????”
I couldn’t get past the moment in the film when Harry and Sally’s relationship goes to shit. The film’s first point of major catharsis, a little over an hour in, left me furious and aching. I hated Harry’s guts and putting myself in Sally’s shoes brought tears to my eyes despite my best efforts to suppress them. The film’s message—no, men and women can’t be friends—felt like a curse.
On my second watch, I found myself more endeared by every moment in the film, even the ones that felt like pressing a half-fresh bruise. Their relationship is a series of pushes and pulls; they fall in and out of each other’s lives, being petty and cruel to each other only to later apologize and forgive. The film’s raw tone toward love acknowledges the intentional and unintentional ways people can hurt one another, and the kinds of resolutions that can follow. I saw myself in scenes where one character hurts the other; I have been both Harry and Sally.
I realized the film wasn’t trying to sell me on love at first sight, on love being easy, on people being perfect for and toward each other. Harry and Sally fall in love the hard way, and it’s worth it. Their journey toward each other feels delightfully charming, despite its moments of immaturity, because it’s honest.
Although one can argue that the film promotes an easy version of love filled with soulmates and destiny, I’d counter that it’s much more hopeful than that: it’s about the inevitable passing of time and its ability to thread coincidence into human relationships. Their segmented relationship seen in vignettes separated by years relies on the uniquely powerful and universal feeling of being wholly yourself, even yourself amplified, with a special person that you hope will be in your life forever.
I realized on my rewatch that the film isn’t dooming all friendships between men and women. It’s saying that men and women can be friends, but they can also be more. Both things can be true at different times, and both can be flawed and painful in different ways. While I understand the appeal of the film’s endless supply of gorgeous scenes set in the New York fall, cozy oversized knit sweaters, and adorable stories of married couples that director Rob Reiner collected and recreated, I ended up finding a lot more comfort in how real Harry and Sally’s characters feel.
My new Letterboxd review reads: “i take it back… i’ve finally (as of a couple months ago?) stepped out of my naïveté to internalize the fact that romantic relationships are messy and imperfect and such hard work, true effort from your entire self, and that’s, like, the whole point. the whole thing.”
I had to hate When Harry Met Sally before I fell in love with it, and I can’t think of a more fitting way to define what makes it a movie I will keep coming back to.