10 Best When Harry Met Sally Moments

When Harry Met Sally (1989), written by the quick-witted Nora Ephron and directed with such tenderness by Rob Reiner, follows the two titular characters’ chance encounters with each other across the span of 12 years. It is a tight and breezy one-hour-and-a-half watch that makes you laugh as much as it makes you cry.

This classic romantic comedy is jam-packed with brilliantly memorable scenes, earning every bit of its legendary status. It rewrites some rules of romance, but primarily operates to illuminate the very best parts of Hollywood’s more sappy side.

In this Movie List, we at The Film Magazine have chosen the funniest, the cleverest and most heartwarming moments from arguably the best romantic comedy of the modern era. These are the 10 Best When Harry Met Sally Moments.


10. When Harry Met Sally

Billy Crystal (left) looks at Meg Ryan (right) as she drives in a great romantic comedy movie.

In 1977, our two main characters are introduced when Sally Albright (Meg Ryan) gives Harry Burns (Billy Crystal) a lift in her car from the University of Chicago to New York City. It is obvious from the get-go that Sally’s optimism contrasts greatly with Harry’s cynicism, immediately creating a humorous dynamic.

What makes this dynamic funnier is what happens when they stop off for food at a roadside diner.

At this point, Harry starts prying into Sally’s sex life, which she at first refuses to engage with. But, upon seeing Harry’s alleged indifference, Sally attempts to prove him wrong about her frigidness.

Upon being asked about why she broke up with her boyfriend, Sally explains that he thought she was cheating on him because of her ‘days-of-the-week underpants.’ She never wore Sunday, because they didn’t make Sunday. Why? “Because of God.”

Recommended for you: When Harry Met Sally Retrospective Review


9. A Chance Encounter in the Sky

Five years after arriving in New York and leaving things on frosty terms, Harry and Sally find each other on the same flight. Both are in relationships – Sally’s is a month long and Harry is engaged. On discussing these relationships, both of their personalities clash just as much, making for more comedic viewing and reinforcing their undeniable chemistry.

It is clear that Sally has become less doe-eyed than she was before. Instead of constantly defending herself against Harry’s schoolboy teasing, she simply resigns to his comments with the brilliant, “It’s amazing. You look like a normal person, but actually you are the angel of death.” On the flip side, it’s clear that Harry has mellowed slightly, as he reveals that he is madly in love with his fiancé.

It is clear that our two protagonists have grown up, but there are still glimpses of their former university-aged selves – that’s character progression.

The scene also uses subtle foreshadowing for the events to come, as Sally makes it clear to Harry that neither herself or her boyfriend are looking to getting married and Harry says that his fiancé is keeping her surname; both small details that become essential.

The plane lands, Harry doubles down on his ‘men and women can’t be friends’ argument, and the pair leave things on even colder terms than before.

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