Holiday Rewind: When Harry Met Sally

When Harry Met Sally. Castle Rock Entertainment 1989.

Being in a completely different chapter in my life than I was when I first watched When Harry Met Sally, I’m not sure if it will have the same effect on me now. This movie was a bit aspirational for me at the time, but now I’m more settled and have different life issues and resonances.

I don’t remember very many scenes outside of the two or three iconic moments, but I also remember the whole thing with the wagon wheel table, which was pretty irrelevant but left an impression for some reason.

Twelve years ago, Harry Burns caught a lift from Chicago to New York with his girlfriend’s best friend Sally Albright. The 18 hour drive did not go well, including when Harry suggests that men and women can’t be just friends because the man will always want to have sex. Seven years ago, Harry and Sally happened to share a flight. Harry suggested that, as they’re both in serious relationships now, they should become friends, but had to admit that his earlier statement stands. Two years ago, Sally and Harry ran into each other again, Harry freshly divorced from his wife who left him for another man, and Sally broken up with her man who didn’t share her life goals. Both clearly hurting, they hit it off and became what each other needed. They quickly fall into a relationship that’s almost a platonic life partnership. Both of them encouraging each other to get back out into the dating scene, they try to set each other up with their best friends Jess and Marie, who instead fall for each other and quickly get married, while Harry and Sally help each other navigate relapses in their respective post-breakup depressions, trying to determine what this thing they have really is.

This movie is entirely dialogue driven, which means the biggest star is Nora Ephron’s script. However, a lot of Harry’s lines don’t sound like a Nora Ephron script, and that’s apparently because most of his part was punched up by Billy Crystal. I understand that it’s fairly common for some actors to get a pass on the script where they or a favorite writer makes them sound the way they sound in every movie, but it does kind of stand out here. It also runs on observational humor, which I understand was a big movement in comedy about that time, but now it just feels like proto-Seinfeld.

The mockumentary segments with decades-married couples telling the stories of how they met is a sweet framing device, but I come up empty at least half the time trying to decide if the particulars of the story being told has some thematic bearing on the chapter about to unfold. I think they’re just stories, but one or two come close enough that it seems like there might be more meaning.

I didn’t remember just how much I was disappointed in the neatness of the resolution initially. They found each other, went through a crisis that forced them to reevaluate what they really meant to each other, and that’s a completely okay resolution. I wanted it to be more relevant to where I was then, and it wasn’t, and I took that out on it a bit. This is a delightfully charming, unconventional romcom that ends up in a conventional place because that’s what makes it a romcom, and that’s okay.

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