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A Blog About Watching Movies (AKA a Blog in Search of a Better Title)

When Harry Met Sally... (1989)

Mac Boyle December 25, 2025

Director: Rob Reiner

Cast: Billy Crystal, Meg Ryan, Carrie Fisher, Bruno Kirby

Have I Seen it Before: Oh, sure.

Did I Like It: And that may be part of the—completely subjective, not at all the fault of the film’s—problem. I haven’t seen it in years. Lora and I were even talking about it while we were watching it, and I’m not entirely sure she and I have ever watched it together in the sixteen years we’ve known each other. Lora seems to think we have, but I’m really not that sure.

The film always seems like—with its trips to The Sharper Image where one can act like they invented karaoke, deep connections over the same movie playing on TV*, and a sweater or two—a time capsule.

It’s also an emotional time capsule, though. If you’re not trapped in a decade-long cycle of will-they/won’t-they, does it play the same? Say, if you’re somehow more like Marie (Fisher) and Jess (Kirby) and despite some troubles have largely settled that part of your life, does the dithering and navel gazing of Harry (Crystal) and Sally (Ryan) still hold any meaning after all these years?

It’s probably a better question than that old, hoary cliché of wondering whether or not Harry and Sally are still together in the ensuing years, but not an entirely unrelated one. I tend to think that if the two protagonists didn’t come to some kind of peace about themselves, the quirks that caused them to come together in a fit of romantic whimsy would probably come back around to make them run for the hills.

But then, if my mind can’t help but go to these kind of quibbles, is it possible the entire genre of the romantic comedy has completely lost its meaning? That’s possible, and would still allow this film to keep its crown as the superlative entry in the genre.

*Given that might, in fact, be a method of connecting over movies that has reached essential extinction, the moment where Harry and Sally disassemble the ending of Casablanca (1942)  hits a bit harder than anything else.

Tags when harry met sally... (1989), rob reiner, billy crystal, meg ryan, carrie fisher, bruno kirby
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Party Now, Apocalypse Later Industries

Where creativity went when it said it was going out for cigarettes.

Where creativity went when it said it was going out for cigarettes.