When it comes to judging a romantic comedy, for me it comes down to two questions: Is it funny? and Is it romantic?
For funny, I need to laugh out loud at least once. I want witty dialogue that's so appropriate that I find myself quoting it when I'm in similar situations. I'm not a fan of gross-out or humiliation humor, which is why most current "romantic comedies" fail for me. I'm the weirdo who cried all the way through There's Something About Mary because to me, all those "funny" situations were so sad and awful.
For romantic, it gets a little more nebulous. I need to want the couple to get together, and I need to be able to see why they should be together. I also want to get the sense that they know why they should be together. Screenwriting teacher Michael Hague joked in a seminar about a movie where the big revelation of feelings should have been "I love you because we're in this movie together," and too often, that's what's going on. Yes, there are going to have to be differences between the characters to have a movie, but you can't spend the whole movie focusing on how different they are without showing any moments of connection and expect me to believe that they belong together. I'm especially not a fan of cheats and shortcuts like the romantic montage set to a pop song with lyrics that tell us what we should be feeling, or contrived big emotional moments, like the cliched "rom com dash" at the end of the movie. I also want there to be more to the relationship than lust, so I'm not a fan of using a hot sex scene as a shortcut to tell us they belong together.
When Harry Met Sally … wins on both counts. The characters have funny quirks, the dialogue is hilarious, and there are brilliant comic set pieces like the infamous diner scene. And yet I never feel like the movie is trying too hard or doing funny things just to be funny. For instance, the infamous diner scene is directly tied to the emotional crisis of the movie. It happens because Harry has just been talking about how he hates to stay overnight after sleeping with a woman, but he doesn't think they mind because he knows they had a good time in bed with him. Then Sally proceeds to prove that he can't be so sure they really had such a good time. But then when they do end up sleeping together, and he does get up to leave, she can't help but remember what he said about his other dates, and she fears she's just another notch on his bedpost he wants to escape. What was hysterically funny becomes emotionally relevant. You can't remove the humor from the movie and still have the same story.
As for romance, this couple seems unlikely in every way, and they have enough differences for funny conflict, but the movie focuses more on their connection, using the differences just as seasoning. We see them have long conversations. We see trust building and growing. We see how they can be honest with each other, how they challenge each other. We can see how they're better together than they are apart, how they make each other better people. I find it interesting that there is a "developing relationship" montage in the movie, but instead of being set to a pop song, it's set to voiceover of a late night phone call between the two of them. The only musical montages are the two Christmas season montages, which contrast between the Christmas when they're friends and the Christmas when they aren't. We do have perhaps one of the earlier examples of the "rom com dash" when Harry realizes his love for Sally and rushes to find her, but I think this one works because he explains why he felt he had to do it. It's not just there because the screenwriter thought it was an obligatory part of that kind of movie.
This may be Meg Ryan's best role and performance of her career, and she seems to have spent the rest of her career either trying to recapture or escape from Sally, without quite grasping what it was about Sally that worked. Sally is an uptight neurotic, but she's so relentlessly perky that it balances out without it falling into Ryan's later "perma-snit" romantic comedy performances. I never would have considered Billy Crystal a romantic leading man, but he's so funny and charming here that I can totally see falling for him. I think this was also Carrie Fisher's best role, making full use of her natural snark.
One thing I found interesting in this viewing was just how absolutely perfect all the dialogue was. Every line zings, and as a writer, I can recognize the work that went into this script. Then those lines are all delivered with perfect timing, nuance and inflection. And yet there's an improvisational quality about all those scenes that makes it seem like these people really are just spontaneously saying these perfect lines in such perfect ways. I almost feel like I'm eavesdropping on a private conversation. I think it helps that the music is used mostly in transitions, and there's no score behind the conversation scenes, which makes it sound less "movie" and more natural. It's really hard to make it look this easy, so this movie is a triumph of writing, acting and directing.
Then there's all the lovely New York scenery (mostly in the fall) and the score of jazz standards, which helped introduce Harry Connick Jr. to the world (I immediately bought the soundtrack, which was part of my discovery of jazz when I was just at the "this is the kind of music I like" stage of discovering jazz -- and I think I need this soundtrack on CD. I'm listening to the cassette now).
But this was also the perfect movie that hit at the perfect time in my life. I saw it late in the summer between my junior and senior years of college. That summer was sort of my "training wheels for adult life" phase. I stayed in Austin and had a job at a weekly entertainment newspaper (a now long-defunct more family-oriented alternative to the Chronicle, for those who know Austin media). That was when Austin was more bust than boom, so you could get cheap apartments, especially in the summer when most of the students were away, so I got a fully furnished apartment in walking distance of campus for a song, and then my friends going away for the summer stashed their stuff with me, so I ended up with a TV and VCR and a couple of stereo systems. My job was mostly part-time, so I still had plenty of free time, and my job meant I knew everything that was going on around town. I dressed up like a grown-up and went to work at the newspaper, lived in a semi-chic (for that time) apartment near the middle of the city, took informal summer courses at the university (including ballet), and went to a lot of movies (sometimes with passes I got at the newspaper). It was all very single-in-the-city stuff, and it was sheer heaven.
So, one afternoon I went to see When Harry Met Sally, since I'd read the press kit at work and our critic liked it. I was hooked pretty much from the beginning, since it started with the heroine having graduated from college and heading to New York to be a journalist -- something I hoped would soon be happening for me. Even Sally's car was a lot like the one I had, though mine was beige (I didn't get a close enough look to judge the make and model, but I think mine was even the same model from several years later). I kind of looked at this movie as a preview of what I hoped my life would soon be like. It was like getting to watch my fantasies play out on the big screen. I realized while watching this time that my senior year wardrobe was very much like Sally's wardrobe in the movie (though I had a fedora instead of a bowler hat). I don't know if that was something I did subconsciously because of the movie or because that's what was in style then, but I definitely seemed to have been going for that look. This is also a rare case of a heroine's hair getting curlier as she became more romantically desirable. Normally, they start at frizzy/curly, then their hair becomes flat and straight when we're supposed to see them as beautiful. I don't know if Sally was supposed to have had a perm or if she was supposed to have had naturally curly hair that she quit blow-drying into submission as she softened and matured, but it was still very validating for me.
And then there was that friends issue, which hit home because most of my closest friends tend to be men. In one of the interview clips they showed of Nora Ephron this week, she said that men didn't really want women friends because they have friends, so if they were friends with women, it was because they wanted something more, and women want men friends because they want to understand men better. I disagree entirely, but maybe it's a geek thing. I tend to have male friends because they're more likely to have interests in common with me. I had a few female friends before college, but in a group, I usually was more comfortable with the guys because I had something to talk about with them. If those guys were friends with me only because they wanted something more, then they never showed it and missed some big opportunities. I had a bad habit of developing crushes on my various guy friends, but looking back, I'm not sure that it was because I actually was attracted to them. It was more about proximity. In junior high, I was the queen of the crush from afar, but when I got to high school, the town was too small for there to be such a thing as "afar," and I think I also realized that my odds would improve significantly if I focused my interests on the guys I actually knew, the ones who liked me enough to hang around with me. From there, it seemed pretty obvious to me that if they liked me enough to hang around with me, and if they realized that I liked them enough to hang around with them, then maybe when it came time for them to ask someone out, I'd be the most likely candidate. Except it didn't work out that way at all. They hung around with me and asked out other girls. That led to a fair amount of pining, so this movie, in which the male friend realizes that his female friend is the love of his life, was essentially my romantic fantasy. It gave me hope.
Looking at it now from the other side of forty, as much as I like the idea of friends becoming lovers, I know that it's really tricky to make it work. For one thing, if you're not both on the same page at the same time, it can get really awkward. For another, if you've known each other well as friends for a long time, you know too much about each other. There have been a few male friends I was attracted to that I never would have dated because there were things about them that I could accept as a friend but that I couldn't tolerate as a girlfriend and that would be a dealbreaker for me as a wife. I also know myself well enough to know that I'm not a person who can be friends with an ex. My exes are pretty much erased from my life (though part of that is that they often become exes by vanishing entirely). Therefore, if a friendship is really valuable to me, any romantic feelings would have to be really, really strong, and what I've seen about the guy would have to lead me to believe we'd be compatible in a romantic relationship or marriage for me to be willing to risk the friendship by taking that leap, and I'd still want to move slowly and cautiously before getting to the point of no return. I think that what I consider friends into lovers is really just a slow-burn relationship, where there's initial attraction, then you become friends and get to know each other on that level before the attraction becomes something stronger and deeper and based on more than the initial vibe, so it just looks like friends becoming lovers, but you were never really "just" friends. You were merely building a foundation for an eventual relationship. I think that's what I tend to write. I certainly no longer dream about any of my male friends looking at me and having that burst of realization that I'm the one they've been looking for all along (most of my male friends are married, anyway).
So I guess I both agree with and differ with the premise of the movie, but it's still my gold standard for romantic comedy. More like that, please! Or, in the language of the film, I'll have what she's having.