"we were friends for a long time, and then we weren't, and then we fell in love"

on love and community in "when harry met sally"

Paramount Pictures

When Harry Met Sally opens with an elderly couple, long married, describing the first time they met. “I was sitting with my friend, Arthur Kornblum, in a restaurant, it was a Horn & Hardart cafeteria, and this beautiful girl walked in,” the man says, gesturing to his wife. “And I turned to Arthur and I said, ‘Arthur, you see that girl? I’m going to marry her.’ And two weeks later we were married and it’s over 50 years later and we’re still married.” The woman pats his arm with a tenderness only people with 50 years of love between them (or actors playing such people) might convey. If you know the convention of romcoms you can see pretty clearly that this is setting up an ending where the same sort of scene will play out with our eponymous couple, Harry and Sally. It’s sweet to imagine the ending before we get started, to wonder immediately how a happily ever after might come from all that we’ll witness first.

But there’s something else in this opening that probably isn’t what When Harry Met Sally is about but that got me thinking all the same. This convention of older couples sharing their meet-cutes happens throughout the film. And of course they’re all different but one thing is the same—and it’s the same for Harry and Sally, too—which is their love is hinged on timing. And not just being in the same place at the same time, but timing in terms of readiness. Both are ready for love of this kind in the same sort of way at the very same moment. That word “ready” even comes up in one of the interstitials, when an older Chinese man says his now-wife was “ready for marriage” and so was he. And when you really think about it, when you think of the people in your life who are happily together—or even when you think about the people you dated or married yourself—isn’t that always the case? That it’s less about the fireworks and magical unions that we fantasize about and think will fix everything and more that you met someone in the conditions in which those things were even possible. Because they, and you, were ready.

I’ll get back to that point in a bit because there’s another thing I’d like to talk about, too. And that’s that watching When Harry Met Sally when you’re older than the characters—with the perspective of age and experience and your own successes and failures in love—you see things a little differently. I always thought this was a perfectly nice romantic movie, but now I think it might be the movie that understands relationships—not just romantic—in the very best and healthiest way possible. Maybe that’s hyperbolic, but bear with me. It’s not that the movie is really a subversion so much as it’s a deconstruction and that’s where I think it succeeds. It cuts into and examines the bonds between people with a knife of plot and circumstance then presents it like an anatomical chart. But in a fun, movie sort of way so you don’t really notice, you’re just entertained. (Nora Ephron rules.)

The reason I revisited When Harry Met Sally in the wee hours of New Year’s Eve is because my friend Angelica sent me a Letterboxd review of the movie by Joshua Briond that she thought would interest me. And hoo boy, what amazingly astute observations Joshua makes! And hoo boy, how his words sort of rewired my whole brain in a lot of ways that I’ll soon get into—and a fair warning that this will be a bit disorganized and from the gut, because that’s how we do it ‘round these parts!—but most importantly because of this bit:

“i think one of the most important *small* moments is when harry’s at the batting cages with jess. and they are talking, and harry almost explicitly states that like, it's different with him and sally (than it is with other women). it's different than like when he usually dates people. 'cause like he has to lie, he has to pretend, and mold himself himself into an image that would ‘make’ the person like him, right? and, this [is] something I've thought about a lot when it comes to the flawed way we kind of approach dating/love/romance/intimacy. and this is just my thesis as to why a lot of our romantic relationships flame out/fail: i think a lot of times our relationships start under misconceptions. well, that's me being nice. honestly, they are started and built on lies 😭”

He goes on to talk about all the ways romantic relationships are hinged on performance and curating ourselves for people so that we’re what we think they’ll like instead of just, you know, being our real selves. And obviously this has always been true in one way or another, even in 1989, but it’s especially true now. Dating apps and social media are really tools of manipulation. You sell an image of yourself, a snippet of yourself, and even if it’s “true” it’s not all of it, of course. It’s not your quirks and neuroses and flaws, it’s not all of the things that might make someone really love you because those are things you discard to be what you think is more palatable. And you can never really live up to the person someone might concoct in their head based on those things because they’re just the loose impressions of a person. They’re just a picture. And even though we know all of this already, what I’m positing is… do we really? Because we keep falling for the same schtick. We keep making ourselves into these people and we keep falling for these people even though it’s all, as Joshua says, a lie.

When Harry Met Sally isn’t about two people falling love based on a lie, though—it’s about two people who fall in love through friendship. And another thing I couldn’t stop thinking about this time around are all of these stupid barriers we’ve put around love in the last few decades, especially these days, through the prominence of therapy talk but also the advice of strangers on Reddit, TikTok, or wherever else you consume your deliverables. And one of those barriers is “don’t date your friends, it never ends well.” I’ve always rejected the logic of people on the internet because I assume most of them are probably not so happy if they are spending all of their time making content or commenting in those spaces. (That’s it’s own kind of performance but they’d never admit it.) Because a “rule” like that is fucking bullshit. Like, why is it so socially acceptable to meet people through blind dates or dating apps or set-ups but it’s “toxic” or “self-destructive” or whatever the hell else to date a friend, someone you actually know—and in many cases, someone you, like, really know? As Joshua writes:

“what i’m saying is people don't really like build up a strong foundation that could only happen through friendship. an honest and intimate foundation upon which you are actively and truly enjoying a person, to actually be friends with a person, to actually truly, truly, truly get to know a person. without all the pressures that come with human baggage and without all the the dishonesty, or the kind of like manipulating. 'cause that's really what a lot of like dating is, right? manipulation! […] there's something that is so liberating and intimate about having the capacity to, in harry’s words, ‘say whatever i want’ to someone. we consider romantic love to be the pinnacle of intimacy, yet MOST couples—married or otherwise—do not possess that level of intimacy. why is that?”

Like, damn, right? And of course there are some caveats to make, like Harry’s insistence in the film that (hetero) men and women can never be friends without wanting to fuck each other. Obviously that’s horseshit and another “rule” worth rejecting. I often hear or read people say they could never date a person whose close friends are the opposite sex. It’s the subject of a zillion Reddit posts. People citing the suspiciousness of such a thing, how it’s disrespectful to your partner. (I cannot speak to how this line of thought transfers to queer relationships because that is not my experience, so pardon the heteronormativeness here.) And all I think when I read stuff like that is that it’s making a problem out of nothing while avoiding the actual disrespectful thing to do to your partner. Which is not the semantics of who they are friends with but your inability to trust them. I think we tend to see the people we date or have dated as possessions instead of as individuals and this logic is one of the biggest symptoms of that. But it’s less trendy and more self-confrontational to look at things that way, so naturally we just blame it on the friend.

And another caveat being that there are of course times when dating a friend is bad news. Sometimes the altar of friendship is more precious than what fucking with it could destroy should things not work out. Dating your very best friend of many years contains an element of sacrifice that’s probably not worth it, especially if that’s someone you never want to lose.

But I think the kind of friendship we see in When Harry Met Sally is—at least in my non-professional opinion—perfect conditions for romance. They meet in 1977 on an awkward road trip, where Sally drives Harry to New York City, and they kind of hate each other. They don’t meet again until 1982 when they’re on the same flight. Their next encounter, five years after that and in a bookstore, is when they sort of give into the randomness of their happenstances and decide to be friends. And over the course of a year they really are just friends. There’s a baseline attraction, which they acknowledge, and one New Year’s Eve kiss, but other than that they are two grown adults who set aside that stuff and just, you know, hang out. Talk. Watch the each other date other people. Get to know each other deeply and fundamentally. They’re also, I think importantly, not each other’s best friends. Sally has Marie, Harry has Jess, and all of them coexist among other friends who hang out together, too.

Which leads me to another little thing I want to talk about before I get back to the romance of it all. Joshua touches on this in his review, too, and that’s the concept of community. This is also, in a way, a movie about community! And what that means is it’s a movie where friendships and relationships and personal connections are not just tight-knit but are also not demarcated by all of the pesky boxes we love to put each other in these days. I’m going to sound very Old Man Yells at Cloud for the rest of this post, but I really feel this enormous division of people in 2020s America—even in friend groups that once intersected—and I think it’s rotting our souls. It’s not all friend groups of course, and I’m sure a lot of it is age, but I’m not that much older than Harry and Sally and so I think it’s worth the comparison. (Although I am the age—36—that Sally cites as the time the clock starts ticking, which I am choosing to ignore.) Of course this is partially a relic of the pandemic but it’s also the axiological walls we’ve put up around the littlest things, like personal interests and couple statuses and whatnot. Nowadays and at this age I feel like we mostly just hang out with certain friends for certain reasons and not all friends at once. And I’m very guilty of this sort of thing, so no judgment, but I kind of miss the not-so-long-ago days when my apartment was a revolving door, people always over for any big or little thing, and when there were parties or backyard hangs and you just invited everyone you know, and whoever could make it would and whoever couldn’t wouldn’t. No big deal. And you met people you never would have otherwise, maybe even people you could date at these things. And now it’s like, OK, I’ll hang with those married couple friends at this place, but I’ll hang out with my single gals here, and I’ll get a movie with this person, and there’s that one friend I only see in that one place. And then you also have to keep in mind everyone’s personal comfort with things because of their various social disorders, so you can’t do xyz for xyz time or else xyz. And sorry if this is a rude observation, but like, what gives? Where’s the comfort of being around people, all sorts of people, and just letting life spill out from that coexistence?* People these days, progressives especially, love to talk about community and the need for it. But they can’t even be in community with their own fucking friends.

And maybe that’s just my experience but I really don’t think it is. I think a lot of people can relate to it because it’s a topic that comes up in conversation with people I know all the time. And I know this isn’t specific to When Harry Met Sally—seeing different friends and people just hanging out at parties and dinners and stuff—but it’s relevant to the overall point I’m making which is that these are the conditions under which we can even find new people to build relationships with. There needs to be a willingness to just be around each other, even if we think it’s going to be uncomfortable. The thing about comfort—again, in my opinion—is that we’ve become a little too obsessed with it. Which is not to say we should disregard it entirely. Obviously we have learned new things since 1989 and one of those things is protecting our peace. But I think we’ve taken that concept and ran with it and now protecting our peace means siloing ourselves into the most comfortable zones possible and lying to ourselves that we’re happier there. Like maybe fuck around and find out that people are the biggest comfort, actually, because they’ll catch you when you fall in a way your phone or your Blu-ray player never will.

And maybe this is big-brained of me or whatever, but I think doing the sorts of adult activities the people in When Harry Met Sally do—like going out for casual coffee with more than one friend or having double-date dinners or playing Pictionary in someone’s living room with a group of people—allows for them to really be just that: adults. I feel like something else we love to do these days is infantilize grown ups with, again, all of these stupid socialized rules we’ve made up and spew out like we’re experts. And we do that—I’m sorry to say—even with our closest friends. We talk to someone who’s made what we perceive to be a mistake like they’re babies and we’re God.

It’s such a minor thing, but I love the movie’s c-plot of Marie’s affair with a married man. Her friends know about it and poke at her about it, but they also know that she knows it’s not the best idea. She even says this aloud multiple times. A lesser or more modern movie would make this into a whole moral journey for Marie, where her friends stage some kind of intervention or hound her with advice she never asked for, or where there’s some tremendous falling out where she’s confronted by the jilted wife so that she’s scared and humiliated and maybe even socially pressured into a more conventional relationship that we in turn are made to believe is much healthier. But in this movie, Marie’s friends don’t really say much about it at all, and they certainly don’t lecture her. They just assume she’ll figure it out for herself and they let her get hurt because she needed that lesson and they knew she’d be OK. And she is! She does learn the lesson for herself, there’s no big deal made of it, and then we see her fall in love with someone she genuinely likes and that’s the end of it.

Which leads me back to the point about romance because this shows up in Harry and Sally’s deal, too. Yet again, I keep thinking of these socialized rules we now live by (unless you’re me, a scoundrel) but that Harry and Sally don’t at all. I was in diapers in 1989 so I wouldn’t know if these rules even really existed then, but I have to assume they probably didn’t. And one big example of this is that Harry is kind of an asshole—even a misogynist at times—and Sally is clearly “too good” for him, but the movie never treats their situation that way. And I can’t help but imagine the ways in which this would be undressed in the context of 2025. We have this thing now where we view the people in our world and lives as all one thing or the other. We are obsessed with shutting people off or pushing them out if they are not 100% ideologically aligned with us. And everyone hates me when I say this but I’ll keep saying it anyway because I think it’s really fucking true: we’ve got to stop being this way. We just do. It doesn’t mean letting real pieces of shit into our lives and forgiving them over and over. There are obviously boundaries to be made. But what I mean is that if we stop child-rearing our peers we could maybe make space for people to know what they’re built for, know what they’re not, and trust them when they move forward with others however they want to. No one shows up to tell Sally she should block Harry from her life because he says dumb shit like men and women can’t be friends without wanting to fuck. There’s no advice column or guru to put this thought in her head either.

Instead, we get to witness two people with big differences learn how to grow into each other, change each other, and come out better equipped for the world and for love. Sally fakes an O out loud to humble Harry into awareness of his misconception, and boom, that’s a lesson learned. Sometimes it’s as easy as just doing something like that and seeing how it flips a thought and makes someone better. Harry does a similar thing by helping Sally get honest about her heartbreak after her split from Joe, the boyfriend she’d recently lived with. They show up for each other like that, and fill in those blank spaces, because they’re friends, first and foremost. And it’s great because our partners should be friends first and foremost. When we date we are ostensibly “auditioning” (for lack of a better word) someone to be the most important person in our life. Which doesn’t mean we overshadow the other important people in our lives—like best friends and family members—but a partner is something different. Someone you choose to be at your side always, someone who will take care of you, someone to do things with and enjoy things with and, if you do it right, die with. And wouldn’t you like to actually like that person, like for real?

But of course there’s so much that goes into these things. Relationships are not easy and don’t fit into boxes and are like fingerprints because each is completely unique. We kind of do ourselves a disservice when we try to make it seem otherwise. But this idea of creating foundations first and letting the other stuff come about the way it needs to seems like a neat way to approach relationships of all kinds. As Joshua writes:

“i just think we need more of that. try to genuinely be fucking friends with the people we admire and seeing where things go and building on top of that *IF* that’s in the cards for all parities of course, and accept if it isn’t. because even if it isn’t, GUESS WHAT, you still have a close fucking friend!! that’s dope as hell to me.”

And like, it’s just really hard to orchestrate or engineer things to be what we want them to be, especially when other people are involved. We cannot control other people. We just can’t! And when you view romantic relationships through a lens of control you’re just sort of in for a superficial experience I think. Which is not to say you can’t find love on the apps or blind dates or whatever—of course you can!—but it requires a brutal form of honesty that you’ve gotta be prepared to show up with. And plenty of people are prepared, because they’re adults and know what they’re capable of, but plenty aren’t and should learn that about themselves. Knowing ourselves is really key to everything, too, because it’s important to maybe know what we actually want before we start involving people in matters of romantic intimacy. I know it’s hard to really trust yourself and maybe you think you know what you want, but we really owe it to ourselves and to others to do the necessary check-ins to keep it real.

Which brings me back to the beginning, that idea of timing. When Harry Met Sally really nails that whole thing, too, although I’m not really sure that’s what it was going for in the way I mean it. But it’s what I extrapolated from it anyway, especially in the scene near the end when Sally finds out her ex Joe is getting married. It’s a significant scene because it’s when she finally admits the breakup hurt like hell. And she says something I think any of us can relate to, and something that peppers all of these advice-y things I’ve referenced, too: “All this time I’ve been saying that he didn’t want to get married, but the truth is he didn’t want to marry me. He didn’t love me.”

And like, here’s the thing, and I’m sure people will disagree but, again, I’ll say it anyway: I don’t necessarily think she’s right. I mean, she is in one sense, which is that they talked about marriage and never did it because they said they didn’t want to. But if you recall the conversation where she first tells Harry this, she says something else important: “When Joe and I started seeing each other we wanted exactly the same thing.” And she goes on to explain how neither of them wanted to get married because they didn’t want it to ruin their sex or spontaneity, but then one day Sally changed her mind. She wanted to get married but Joe didn’t and so they split. But fast-forward a year and now he’s engaged so she thinks it must be that he never loved her, and just that he finally found someone he loved enough to change his mind. And I think we largely accept that this is how it always happens, that someone just doesn’t like you enough so they move on. Maybe that person even tells you they don’t like or love you and maybe they even mean it. But maybe it’s also something they’ve told themselves because they can’t admit a deeper possibility: the possibility that they just aren’t ready for you or for that thing.

If you flock to spaces online where people talk about breakups, you’ll hear something like, “they just don’t want you.” And it’s harsh but it serves a purpose in that it’s an answer that can help you move on. But I think the reality might be something way more tragic in its incomprehensibility, and it’s a slight reframing of that same idea: It’s not necessarily that they don’t want you, it’s that they don’t want to. Because if you really think about it—generally speaking—someone doesn’t get with you and stay with you for months or years because they don’t like you or want you or even love you. They might like or want or love you so much but maybe they don’t like themselves. Or maybe they haven’t figured out what they really want. Or maybe they’ve convinced themselves you don’t fit into their life the way they envisioned it. And, hey, maybe they really don’t want you. But that’s why I think the to instead of the you is more inclusive because it’s not always so simple as there’s something not right about you for this person. The sadder truth is that there might be and they just can’t see it. Because they’re just not ready.

And the reason I think that’s sadder is because it means that theoretically you might have met all sorts of soulmates in your life. You might have dated them or even married them. They might be perfectly right for you. And of course it’s probably more often the case that the person really wasn’t right, because you fought or purposely hurt each other or live far apart or have different religious beliefs or are too close of friends or there’s abuse and jealousy and insecurity. But in Sally’s case there was none of that with Joe. Everything was right there. They just, for some intangible reason, found themselves at a sudden crossroads. And the tragedy is the continuation of that thought because they might have been right for you in almost every way except for one little thing—which means that they actually weren’t right for you. Because that’s always how it is. It’s the tragedy of love. Sometimes the wrongness is a matter of one single misalignment that’s just too strong to rewire.

But the whole “they just don’t want you” thing is the foundation on which we’ve built all of this modern advice stuff. Because it’s a finer line to draw. And all of those other things spill out of that, all of those theories and diagnoses and designations. To me these are all kind of like conspiracy theories because our human brains cannot accept that most things in this life and this world cannot be solved or explained by formulas. Even this whole timing thing is my own attempt to ~figure it all out~ and of course that’s a fool’s errand and I’m also no expert. (And I realize the irony of me calling those other people performative losers for acting like they know better and here I am writing all this. But I guess because I’m being honest about that maybe it’s less performative? Idk.) The reason I’m here, attempting to rationalize relationships in a way that’s not an answer, is because time as we know is a construct. It’s another thing we’ve created to make sense of the great wide expanse of what could be nothing but what we’ve organized into order. And love is a lot like that, I think. Finding the right person is just as unquantifiable as the reasons or exactitude of our own existence. Some things just are.

So it’s not that Joe didn’t love Sally, necessarily. It’s that her mind changed and what was once the same page was suddenly a whole new book. But then later—and here’s where the tragedy comes in—something flipped in Joe, something unidentifiable to us or maybe even to him because these things often are. And suddenly he was ready. But Sally was gone now and the other girl was there and wanted the same things and that’s just how these things work. We can’t just wait around for people to hopefully change because sometimes they’re never ready, or maybe they never really liked the version of you they met while you performed her, or whatever whatever whatever. We love to get lost in the whatevers. And I don’t think those whatevers are something we should just saw off because allowing the pain of them is what makes us humans and not AI bots. But there’s a limit to how long we should allow our mind to float there. We do need to move on, and usually quickly, because when we do there is often our own version of Joe finding his wife. For Sally, it’s Harry.

It’s kind of funny that this all made me think of timing because when you strip it away the movie is about time in its other forms, too. It’s about the years that pass and what happens to people in the midst of them. The movie even ends on New Year’s, the restarting of the clock. But it’s also most importantly about who we spend that time with and how we get to know them. Really know them. And that’s why I love Joshua’s theory about building everything on a foundation of friendship. Not because you’re necessarily looking for a romantic partner or want to turn a friend into one. (If you’re only befriending a person with that intention then you’re just 3D-chessing the whole performance thing again.) But because true friendship is this everlasting thing. It’s the thing, I believe, from which everything grows. Investing in friendships means investing in community and that makes everything stronger. It makes you stronger. And even if you don’t wind up with a lover, you have at least, as Joshua said, made a close fucking friend!

And the way this all ties back to When Harry Met Sally as a larger picture goes back to the elderly couples. The man in the opening scene tells the story of meeting his wife while sitting beside his friend Arthur. In another snippet, a man talks about reconnecting with an ex-wife at a friend’s funeral. Harry and Sally first meet when Harry’s girlfriend, Sally’s friend, asks her to drive him cross-country. And maybe these are all abstract ways of lovers connecting through friendship, but it’s there all the same, isn’t it? This stuff is all random at the end of the day, how we intersect, and this isn’t necessarily the way to move through the pursuit of romance. Of course it’s not. But it’s a way that sounds pretty damn cool to me. Liking someone as a pal first—free of all the ruckus of expectation and advice and performance and rules—then letting time just do its thing.

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*Note: I know that things like COVID cautiousness interfere with socializations, but there are still ways to share communal spaces with lots of people if you’re just careful. There are whole organizations creating safe spaces for people with concerns about all sorts of different things! So I don’t really see that as an excuse.