Movies We Love: When Harry Met Sally


When Harry Met Sally (1989)

No, no, you did not have great sex with Sheldon. A Sheldon can do your income taxes. If you need a root canal, Sheldon’s your man. But humpin’ and pumpin’ is not Sheldon’s strong suit. It’s the name. “Do it to me, Sheldon. You’re an animal, Sheldon. Ride me, big Shel-don.” Doesn’t work.


Harry Burns (Billy Crystal) and Sally Albright (Meg Ryan) meet while sharing a ride from Chicago to New York City after college. After some awkward situations and interesting conversation, they part ways a little less than amicably. Five years later, they bump into each other again, and once again part under less than ideal conditions. Five more years go by and both have seen their share of love’s ups and downs. This time, however, their friendship is able to blossom, and as it develops the central question of the film is tested: “Can men and women truly be friends?”

Why We Love It

I’m not ashamed to say that I love a good romantic comedy. The problem is, as always, that there are far too few romantic comedies that are even worth the ink printed on the ticket, let alone the cost of two tickets and the popcorn and drinks my wife can’t seem to see a movie without. For every Love Actually, there’s a Maid in Manhattan, Failure to Launch, 27 Dresses, or any other number of generic romantic comedies that just don’t seem to have any heart, or, more importantly, any intelligence. And that’s really the problem. The cookie cutter romantic comedy has become a bland, senseless, predictable, and completely unrealistic take on love with one-dimensional characters, terrible acting, and lackluster writing. Fortunately, this overabundance of truly shitty movies makes one appreciate those gems that really shine out as not only good within the genre, but good overall. And one such movie, my personal favorite, is When Harry Met Sally.

There is just so much to like about this film. It has interesting, likable characters with just enough quirk, a great script, solid directing, and wonderful performances. It’s the kind of old-school romantic comedy that they just don’t make anymore. Films in this genre were classically meant to poke fun at the relationships between human beings. They were set up to focus on the differences between men and women and how those differences were the foundation of the problems between them. In the end, the characters learned to embrace those differences, and in doing so, came to the conclusion that they weren’t really that different after all. When Harry Met Sally is also about relationships but is expanded to include the concept of friendship between a man and a woman. Harry confidently claims that men and women can’t be friends because the sex always gets in the way, and the question whether or not this is true is at the heart of Nora Ephron’s Oscar-nominated script. By asking this question, it is given the avenue to rise above the generic genre fare and explore the nature of platonic friendships and romantic relationships, how and where they intersect, and why they are essential to our understanding of the human condition.

Structurally, When Harry Met Sally is presented in a way that I think works very effectively. We first meet Harry and Sally right out of college as they drive to NYC together. They interact and move on. We see them again five years later. They once again interact and move on. Finally, we see them after five more years, and this is where the relationship that was simply cordial before takes off, since both characters have recently hit a low point in their love lives and could use a friend. It’s a nice way to get a sense of these characters and give the viewer a feeling of growth. Also, When Harry Met Sally is framed within and sprinkled with a series of interviews about people’s relationships. According to director Rob Reiner, the stories are true, though they are told by actors playing the parts of the married couples. These interviews are very effective at setting the tone of how the nature of relationships is viewed within the setting of the film. Since these stories are true, it also gives a sense of realism, and we hear about the kind of relationships that we’ve all heard from friends, parents, grandparents, or other acquaintances.

I remember my mother telling me a story about how my grandmother broke up with my grandfather before their high school prom so that she could go with someone that knew how to dance. Afterward, they got back together. Those are exactly the kind of stories you will hear told, presented in a way that is believable and makes you think, “It sure is crazy how people meet and fall in love.” And that’s the feeling you are supposed to take into the rest of the movie as you follow Harry and Sally on their own journey through meeting, friendship, and beyond.

But really, the true beauty of this film is how it portrays the characters of Harry Burns and Sally Albright. They are given a real depth, and we are allowed to see into both their lives and how the effect of their romantic relationships and friendship between each other shapes their feelings, reactions, and emotional understanding. Unlike most romantic comedies, especially these days, both characters are given the chance to grow, interact, experience, and make choices, just like real people. All too often, we see characters (usually men) who simply exist and have no real weight. They are there for the sole purpose of giving the main character an outside stimulus for personal reactions and plot advancement. They are “reacted to” instead of “interacted with.” When Harry Met Sally gets it right, and we are given characters that not only feel believable but are also relatable. Their words resonate because we’ve heard it all before, not just in movies and on television but at bars, in living rooms, and on the phone.

Speaking of the characters, I have to say something about the performances of Billy Crystal, Meg Ryan, Carrie Fisher, and Bruno Kirby. In few romantic comedies will you find a set of performances as strong as in When Harry Met Sally. Though Kirby and Fisher aren’t given a whole lot, they do a great job with transcending the typical “best friend” roles that we see all the time. Plus, their budding relationship and eventual marriage give them more to work with and prove to be a nice addition to the story of Harry and Sally. Meg Ryan also does a magnificent job, making Sally simultaneously adorable and maddening. She perfectly embodies the quirky girl that you just can’t help to love no matter how annoying she might be, and it’s no wonder she was considered the Queen of Romantic Comedies from this point on. But the true star, in my opinion, is Billy Crystal. He is hilarious and brings an emotional weight to Harry that I feel really carries the movie. There are plenty out there who disagree and think Billy Crystal isn’t much of a romantic lead, but I think he’s one of the best I’ve ever seen.

Moment We Fell In Love

In the film industry, it is generally understood that the first ten pages of a script/ten minutes of a movie are the most important. And in my opinion When Harry Met Sally has some of the best opening scenes of any movie, romantic comedy or otherwise. From the beginning of their road trip to New York City to when Sally drops Harry off at Washington Square Park, we are treated to true cinematic gold and some of the most hilarious interactions in the movie. That’s not to say the film starts going downhill afterward, but if a viewer ever needed a comedic hook to keep watching a film, feel free to take your pick from any number in the opening scenes.

Final Thoughts

If you made it this far, I’m sure you can tell that I have some serious love for this film. Maybe it’s because I relate to Harry and find his view on the world pretty damn entertaining. Or maybe it’s because my own wife reminds me a lot of Sally. Like her, she likes to order food in some of the most frustrating ways imaginable, checks to make sure each letter doesn’t get stuck in a postal drop box, and is pretty much the worst kind of high maintenance (because she thinks she’s low maintenance). Or perhaps it’s the universal exploration of friendship, love, and the nature of human relationships. My guess is all three, and that’s where this film really triumphs. Creating deep, interesting, relatable, and funny characters is one thing. Crafting a rich and emotional story that stays timeless by focusing on the depth of love and how it evolves through a relationship is another. Expertly putting them together, especially in a romantic comedy, is a rare occurrence, and that’s why When Harry Met Sally is really a movie we love.

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