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How Rob Reiner taught me the best lessons about love

December 17, 2025

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The Independent

After the shocking death of the US filmmaker and his wife, Elizabeth Day ponders her zeal for 'When Harry Met Sally'

How Rob Reiner taught me the best lessons about love

I don’t remember the first time I watched When Harry Met Sally.

It’s not that the film was in any way forgettable - far from it. It’s because I love When Harry Met Sally to such an extent that I have now watched it countless times at many different moments in my life. It has influenced the way I see the world so deeply that I can no longer pinpoint one single occasion as having any greater magnitude than another. Instead, the movie has become part of the philosophical fabric of my worldview. If TS Eliot measured out his life in coffee spoons, perhaps I measure mine out in When Harry Met Sally references.

Whenever I play Pictionary, I will always think of the scene where Harry (Billy Crystal), Sally (Meg Ryan) and their respective romantic partners do the same, and Sally gets outrageously frustrated that no one guesses her manic illustration for “baby talk”. It’s such a tiny, seemingly trivial moment, but for me, it goes to the heart of what it means for one person to be known (or not) by another. It’s about the yearning we all have for that understanding; the all-encompassing kind that accepts and welcomes our flaws and our idiosyncrasies and our inability to draw a convincing baby.

When I went through devastating romantic breakups in my thirties, I would recall the bit where Sally sobs and tells Harry that she’s realised the truth of why her ex dumped her: not because he didn’t see the same future as she did (family, kids) but because he didn’t see that future with her.

imageWhen I wrote my book, Friendaholic

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