Two things herald fall: when we’re all pressing play on the exact same Earth, Wind & Fire song, and when, finally, it feels like the only thing to do is stay in, pour a glass of wine, and watch When Harry Met Sally. September hits, the weather starts to dip into the high 60s, I have an indescribable desire to start wearing tweed. (Every year I have two goals, which I fail spectacularly at: to dress like Meg Ryan in When Harry Met Sally, with blazers and slacks and maybe a hat, or to dress like Faye Dunaway in Network, with silk shirts and pencil skirts and a corner office.) The biggest When Harry Met Sally line is “I’ll have what she’s having.” The best When Harry Met Sally line is Carrie Fisher pulling out her Rolodex at lunch to find her friend a boyfriend, hearing that the man she’s submitted for approval is now married, and instead of throwing out the card she simply folds down a corner and adds his name back into the rotation. “Really?” she says. “Married.”
But the line that I think about most, and find myself mumbling aloud for no reason in particular, comes much earlier in the movie. Five years after their drive from Chicago to New York together, Harry and Sally run into each other on a flight. She’s in the first flush of a relationship with Harry’s neighbor; he’s getting married soon. When Sally hears this, she’s naturally incredulous: What could make this perma-bachelor settle down? “You know, you just get to a certain point where you get tired of the whole thing,” he begins. “The whole life-of-a-single-guy thing. You meet someone, you have the safe lunch, you decide you like each other enough to move on to dinner. You go dancing, you do the white-man’s overbite, go back to her place, you have sex. And the minute you’re finished, you know what goes through your mind? How long do I have to lie here and hold her before I can get up and go home. Is 30 seconds enough?” Sally gasps. “That’s what you’re thinking? Is that true?” Harry nods. “Sure! All men think that. How long do you want to be held afterwards? All night, right? See there’s your problem: somewhere between 30 seconds and all night is your problem.”
On one level I love this line because I share some of the Sally character’s pointless neuroses. “I don’t have a problem,” she snaps back, brow furrowed. He looks at her pathetically and nods: “Yeah, you do.”
Not all of When Harry Met Sally has aged well, but it’s still a fabulously clever movie. These people wear big sweaters; they live on the Upper West Side; they go to New Year’s parties with actual open bars, not just a couple wine bottles in someone’s living room! These characters talk frankly, and funnily, about having good sex and bad sex, having good relationships and soured ones. It’s laughable how inscrutable these two hyperverbal people are: “Somewhere between 30 seconds and all night is your problem” is vexingly vague, but also generally funny. At the 29th second, you know, you’re fine. Don’t let that timer get to 30 or you’re screwed. (An hour-ish later, this line pops into the audience’s mind again when Harry and Sally sleep together, and we see his face of panic when he’s caught in the trap of his own thoughts: It’s at the 31st second that he seems to go white and want to run out of Sally’s apartment, down her street, all the way home.)
For how obsessive and anxiety-riddled he is, there’s something hilarious about the way Harry doles out his dozen-plus observations about people and and people-in-relationships, and how often these observations are incorrect. (It is insane to imagine that this character is supposed to be 26-ish and making this lofty declaration about love, and I say this as a 26-year-old person.) His certainty — probably based on nothing — is so funny to me, and the way he feels sort of bad about having to break this news to Sally, a woman he loves to make assumptions about: See there’s your problem: somewhere between 30 seconds and all night is your problem. You almost forget, in the moment, that he’s selling something so stupid with his boyish confidence. So many things can happen between 30 seconds and all night, so many little mistakes or awkward moments, and he really believed that there was an opportunity there to be loved more, or loved less.
Sally is obsessed with optimizing for everything — does a slice of pie taste better with ice cream on top, or with whipped cream on the side? — and Harry does too. But this movie exists to work against the idea that you can optimize a new friend, or falling in love. There’s an undercurrent of insecurity: Has this relationship expired? Is this person coming into my life at the best possible time? Is something happening here that I’m not seeing? So much of life is, rather rudely, being in the right place at the right time; Harry and Sally had several weird places at right times, or perfect places at awkward times, until New Year’s Eve when Billy Crystal and his weather-inappropriate crew neck have to fast-walk through New York City to confess his love. He has this great line — “See there’s your problem, somewhere between 30 seconds and all night is your problem” — and it ends up not even mattering.
But still, I think about this line and its fixed confidence and its mystical wrongness all the time. No to be on my ’90s white-romantic-comedy-lead shit, but I am a problem-prone person. I overthink minor decisions, and can deliberate for hours over small details, usually over things that really matter to no one else but myself. Should I start the dishwasher now or when I get home? Should I reply to that email now, or wait to do it first thing in the morning? Does it make sense to invest in a linen comforter now, or will I pack it away in a few weeks, when fall is fully here? I have four pairs of basically identical jeans. I say yes to so many things I really have no intention of ever doing. (Like buying plants, or being on a panel, or actually sitting down to color in one of those intricate, bougie coloring books.) I repeat to myself like a pointless mantra, a private joke: “See there’s your problem. Somewhere between 30 seconds and all night is your problem.“
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