If it is true that cynics are disappointed romantics, the story of two New Yorkers who meet cute not once, not twice, but three times, become friends, watch the sex ruin the friendship (anticipating a storyline Seinfeld would use several years later), only to have a GRAND GESTURE by the scorned man result in the couple’s marriage, it is no wonder When Harry Met Sally is a thing I love.
WHMS works for many reasons, but for me, the two primary ones are the outstanding cast and screenplay. Billy Crystal’s Harry and Meg Ryan’s Sally establish their chemistry right out of the gate and the zingers they hurl during the course of the movie cement their bond. He is cynical but vulnerable, she is sensible but independent. The movie’s cultural resonance can be summed up by pondering the innumerable conversations raised by its central conceit: can men and women be friends?
As in life, the answer to that question is not a simple yes or no, and Nora Ephron’s screenplay marinates in the gray area between the two. People may not change, but they mature around the edges. Harry is an obnoxious boor when we meet him fresh out of college, but by his mid-thirties and fresh off a messy divorce, he is both curdled and chastened. He may try to revenge fuck his way through New York (Billy Crystal as a lothario *is* a bit dubious) but it cannot mask the pain he feels when he inevitably runs into his ex-wife. Sally is prim and serious as a college graduate, but that transforms into independence and confidence 10 years later without losing her no-bullshit attitude.
Instead of growing apart as many couples do who meet young, Harry and Sally grow closer as they age and come to appreciate how they complement one another. They do much of the spade work of a relationship outside the context of dating, providing the emotional support we come to appreciate in a partner without the romantic commitment. While their best friends Jess (Bruno Kirby) and Marie (Carrie Fisher) rejoice when Harry and Sally do consummate their bond, it splits them apart over “what it means.” It is not until they see what life looks like without the other that they realize they should be together.
Sure, it is neat and pat and Hollywood does love the grand gesture (see, e.g., John Cusack in Say Anything) but don’t we all want that moment too? A revelation that we have found that person who we want to spend the rest of our lives with and we want that to start RIGHT NOW? Ephron’s unashamed answer, to quote Sally is “Yes! YES! YES!” Not only do Harry and Sally end up together, but Jess and Marie get their own meet cute when they are set up on dates with Harry and Sally but gravitate to each other instead. And if the point is not driven home hard enough, Ephron splices in interviews with aged couples who recount their own courtship and coupling.
WHMS also avoids one of the more pernicious rom-com tropes of recent vintage - the woman as “hot mess” (See, e.g., any Katherine Heigl or Kate Hudson movie. See also, Trainwreck). Sally is no damsel in distress. She is ballsy enough to spill the beans on faked orgasms but also prideful enough to know that getting under someone to get over someone is a fool’s errand. She sleeps with Harry in a moment of weakness, but kicks his ass to the curb when he makes the encounter sound like a mercy fuck.
While it is fair to criticize the New York of WHMS as let’s just say, lacking the diversity for which the city is known, it also heralded an era of romantic comedies like Sleepless in Seattle, You’ve Got Mail, and Pretty Woman among many others along with anticipating the comic stylings of a little show we like to call Seinfeld. It also offers a glimmer of hope for cynics who question whether they will get their own happy ending. Not too shabby for a movie that takes the standard rom-com premise - an opposites attract love story - and does it better than anything that has come out since then.
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