When Harry Met Sally… (1989)

directed by Rob Reiner

Jenn Montooth

The first time I watched When Harry Met Sally, I had just turned 14 and was suffering through my freshman year of high school. Earlier in the day, before I watched the movie, my mother introduced me to her new flame of the month. I could tell by my mother’s rare good mood that this was early on in their short relationship. He wanted to win over my sister and me by taking us shopping for the day, and for the life of me I can’t remember anything about that part of the day. What I do remember, however, is my mom and her new man, whom I had known for about five hours, suggesting that we all stay at a motel for the night, even though the sun wasn’t even fully down yet and we were only an hour away from home. We got to this empty, dirty parking lot and her beau handed me the keys to the room that my sister and I would be staying in, only a “short walk” away from their room.

My sister has always been the deepest sleeper—something I have always been envious of. So before we even got to dive into how absurdly weird and uncomfortable this situation was, I heard her familiar snores. I was thankful to look over and see a TV, the only other piece of furniture in the room. And the only tiny piece of luck that I received was discovering When Harry Met Sally on cable, at the beginning of the movie. A little piece of heaven in a pre-streaming world. And within the first few minutes of this movie, I knew I had stumbled upon something amazing and life-changing for me. In a time of my life where I felt in danger all the time, I had found the most grounding and comforting movie to put me at ease, and teach me a thing or two about love.

In the beginning of this movie, Harry and Sally have just finished college and are carpooling together to New York City. They’ve just met at the same time we meet them as viewers, and we’re made to believe these two are way too different to ever fall in love. Harry is dark yet goofy, perverted, and selfish. He has this neurotic tendency to go on rants for just about everything, and it’s clear Sally has no idea how to handle this. Meanwhile, Sally is uptight, serious, and also a little doe-eyed (“I haven’t had any life experience yet!”). Her neurotic tendency is to keep everything in her life structured and controlled. Even the way she orders dinner completely baffles Harry. This car ride to New York is certainly the only reason why these two would ever be in the same space together with this time to converse. When they say goodbye to one another, you’re convinced they’ll never speak again. The second time they meet—accidentally, on an airplane—six years later, they still have nothing to connect on. Harry doesn’t recognize Sally until she is giving a ten-minute-long drink order to the flight attendant, and while Harry is going off on one of his signature rants, Sally says, “It’s amazing. You look like a normal person but you are actually the angel of death.”

It isn’t until these two are in their early thirties and going through their first adult heartbreaks that they have some common ground. There is such an ease to their connection the third time around. They recognize each other at a bookstore, and when Harry asks with concern about Sally’s breakup, the scene instantly, and geniusly, switches to her confiding with Harry over coffee, showing us all just how well they’re hitting it off. Up until now we’ve only seem Sally frown or avoid eye contact with Harry, but it’s her that then asks him to dinner sometime, as a way to become friends.

As a 14 year old, I was mesmerized by Meg Ryan’s character. She was independent and so comfortable with herself. Seeing a woman my mother’s age who took care of herself and had such a full life was a bit mind-boggling for me. Her role also broke away from the traditional female role of being defined as “overly emotional” and “desperate for a man.” Her traits were exactly the opposite. I’m not sure I knew a woman could have this kind of life before I watched this film. It was also the first time I saw two people become friends before they fell in love. Neither of them were desperate for love, yet they saw the importance of friendship with the hope of someday finding love.

I had a single mother who had a combination of untreated bipolar disorder and the desperate need to find a new husband. We lived in a small, mainly conservative town where single women, especially parents, were deemed “sad,” so I’m sure that societal pressure did not help her. She had married my father, had two kids a year apart, and divorced only two years after I was born. I grew up watching her date. I also grew up with the guilt of making her a single parent. Anytime she had a reminder from a friend, a television commercial, or a doctor explaining that her children were anxious because they didn’t have a male influence in their lives, my mother would go into a deep emotional spiral. I know it’s incredibly hard to be a single parent, but I always had the impression that finding a man came first, over me. And when I found out over text message that she had gotten married and moved out of the house while I was at school, I realized my gut feeling had been right all along.

Growing up with this movie was an amazing resource for me as I suffered through the dating world, because the film seemed to cover every awful struggle while dating in your twenties. When I had my first real heartbreak at 18, when my partner cheated on me, I felt solidarity with Harry’s miserable groans and sluggish behavior after his wife left him for another man (“Maybe I only miss the idea of Helen... No, I miss the whole Helen”). When I was tugged around by an engaged man, I found hilarity and comfort in Carrie Fisher’s character, who constantly seemed shocked that her married husband wasn’t going to leave his wife. (“He just spent 120 dollars on a new nightgown for his wife; I don’t think he’s ever going to leave her”). After experiencing the painful awkwardness of sleeping with a friend and seeing their behavior change afterwards, I found company in Harry and Sally’s similarly awkward relationship after having sex for the first time (“Isn’t it nice that we can just sit here and not talk?”).

This movie showed me all of the tragedies of dating, but it also taught me how to be independent, learn from my heartaches and mistakes, and to seek friendship before love. It seems fitting now that as I’m writing this I’m also celebrating my two year anniversary with my fiance, who was my best friend for over a year before we started dating. I am thankful for the desire I had from a young age to search for a healthier version of myself both alone and with a partner. I am especially thankful that When Harry Met Sally showed me what that could look like.