When Harry Met Sally… (1989)

The Great Movie Re-Watch

When Harry Met Sally… (1989)


Rob Reiner


Nora Ephron


Billy Crystal

Meg Ryan

Carrie Fisher

Bruno Kirby


Harry and Sally have known each other for years, and are very good friends, but they fear sex would ruin the friendship.


When Harry Met Sally… is one of the best romance movies ever made. So many of the movies I’ve watched recently haven’t aged particularly well, but that wasn’t the case with When Harry Met Sally… Yeah, it would have been nice if college Billy Crystal hadn’t been so obsessed with sex, but it was a pretty good representation of a specific section of college man. Maybe not the same group as originally intended, but I’m sure many college guys still believe that men and women can’t be friends.

Watching the evolution of Crystal and Ryan’s relationship is awesome. It could have so easily been too dramatic, it’s the type of story that would work as a straight drama, but the comedy makes it the fantastic movie it is.

Both characters are filled with quirks, but I wondered if Ryan’s character was on the spectrum. Her whole putting the envelopes in the mailbox one at a time and how the sheets had to be a certain way when she slept seemed at least a bit OCD. The way she ordered her food takes picky to the extreme, and yet she had a freaking coconut cake at her wedding. That is one of the meanest things you can do to wedding guests. I will never forget the disappointment I felt as a child after suffering through a horribly long wedding ceremony only to be given yucky coconut cake. It was an unforgivable betrayal.

Crystal plays the same character as he does in most of the movies I’ve watched him in, but he grows. He goes from the college bro who doesn’t believe men and women can be friends to being good friends with a woman. Eventually, yes, their feelings change, but they are friends for a while before that happens. Friends to lovers is one of my favorite tropes. I married my best friend, so I love reading it happen to other people.

When Harry Met Sally… is famous for a particular scene involving Ryan in a delicatessen. I can’t listen to this scene. I don’t consider myself a prude, but it makes me so uncomfortable that I have to either fast-forward or mute it while it’s happening. I try, but it’s too intimate and makes me embarrassed, so I can’t watch.

On the other side of things, when Crystal has his declaration at the end, I’ve got a big stupid grin on my face, and I can’t look away. There’s a reason this film is on all the big lists. Not just romance lists, either. It is all around a great movie.


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