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Wayback Wednesday: When Harry Met Sally… (1989)

I think we’ll ALL have what she’s having.

I realize I’m a day early, but what can I do? It’s not my fault the universe couldn’t be convenient enough to have Valentine’s Day fall on a Wednesday this year. On that note… Happy Valentine’s Day! In honour of the most romantic day of the year, I knew that I had to watch a romantic comedy but here’s the issue: I fucking love romantic comedies. I love the ones that touch your heart and re-affirm your belief in romance, and I love the ones that are full of cliché garbage that you laugh at with your friends. The romantic comedy well runs deep and I was genuinely overloaded with options. I considered everything from Roman Holiday (1953) to How to Lose a Guy in 10 Days (2003). By the way, totally down to review either of those next Valentine’s Day or literally just any upcoming Wednesday. Eventually, I decided on one of the most beloved romantic comedies of all time: When Harry Met Sally…(1989).

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Credit: / Columbia Pictures

Directed by Rob Reiner and written by Nora Ephron, When Harry Met Sally… follows the titular characters as they repeatedly meet each other over the course of 10 years, slowly becoming closer each time. The final time they meet, they bond over shared heartbreaks and begin a deep and meaningful friendship that has their friends convinced they need to become a couple. Harry and Sally however, are “just friends.”

When Harry Met Sally… is my kind of movie. A romantic comedy with charming leads that takes place in New York? With a fantastic script from the writer of Sleepless in Seattle (1993) and Julie & Julia (2009)? Directed by the man who gave us Stand by Me (1986) and The Princess Bride (1987)? Fuck yes to all of this! I have such an admiration for Rob Reiner and Nora Ephron, as well as the movie’s leads, Billy Crystal and Meg Ryan, that there’s no way I could resist reviewing this movie at some point. I’ve seen When Harry Met Sally… a few times now and I’m thrilled to report that it’s one of those movies that each time I watch it, I pick up on a new joke or gain a new perspective on life. My favourite movies are the ones that are constantly surprising me.

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Credit: / Columbia Pictures

What comes as no surprise is how incredible Crystal and Ryan are in this movie. Look, we’ll get to Billy Crystal in a minute, but I need to talk about Meg Ryan right this second. She’s the Official Undisputed Queen of Rom-Coms, right? I mean, Sleepless in Seattle, You’ve Got Mail (1998), Kate & Leopold (2001)…she’s like the LeBron James of romantic comedies. Always adorably effervescent, what I think rom-com fans love about Ryan is that she’s able to take whatever character she’s given and make her feel like she’s one of your friends. You feel attached to Sally because either you’ve been in her situation yourself, or you’ve dealt with friends who have. Whether it’s sobbing hysterically, singing karaoke in a crowded store, or speaking in a ridiculous accent, Ryan gives herself fully to the story, performing the brand of quirky physical comedy that people expect from a rom-com lead.

Speaking of giving herself fully to the story, let’s talk about that diner scene. Don’t even pretend like you don’t know what I’m talking about. The scene where Harry believes he’d be able to tell the difference between a woman having a real orgasm and faking it leaving Sally to fake an orgasm in the middle of their lunch, is nothing short of iconic. Again, Ryan completely commits to the role, giving us not only one of the most memorable scenes in film, but also one of the simplest and funniest punchlines ever: “I’ll have what she’s having.”

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Credit: / Columbia Pictures
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Credit: / Columbia Pictures

What’s great about When Harry Met Sally… is that it’s not a one-sided story about one of them chasing after the other. Harry and Sally stand on equal ground in terms of impact to the story, and both Meg Ryan and Billy Crystal are equally the star of the movie. While Ryan steals the show with her abundance of charisma, Crystal does the same with his impeccable comedic timing. If you had told me that professional comedian Billy Crystal had written the script, I’d have no problem believing you. Many of Harry’s lines, often humorous monologues delivered to Sally or his friend Jess, feel like they’re plucked right out of a stand-up set. Much like Jack Black in The Holiday (2006) – that movie is fucking perfection, don’t try me – Crystal probably isn’t the first person that comes to mind when you think of “rom-com lead.” However, it’s that sense of wit, charm, and intense earnestness that Crystal brings to Harry that leave you unable to think of anyone else who could play the role. Self-deprecating, grimly comedic, and lovably quirky, the rom-com genre could only benefit from more characters like Harry Burns.

Sigh…don’t we all wish we had a friendship like Harry and Sally’s? Waking up at 4 a.m., calling your best friend, finding out they’re still awake too, and then staying up late watching the same movie while you casually catch each other up with what’s going on in your lives?  Sure, that can be a little intense, but isn’t friendship one of those few areas in life where a little intensity is needed? Here’s something I will forever accept as a compliment: “He was an intense friend.” Love it. By the way, this was basically my not-so-subtle plea to have someone wake up at 4 a.m. and watch Clueless (1995) with me.

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Credit: / Columbia Pictures

Speaking of friends, also starring in this movie are Bruno Kirby and Carrie Fisher as Harry and Sally’s friends, Jess and Marie, respectively. CARRIE FUCKING FISHER. Kirby is a lot of fun and serves as a great straight-man for Crystal, but I’m sorry, in Jess and Marie’s scenes Fisher ensures that the spotlight is pointed directly at her. Obviously, the Star Wars series (1977 – present) is what everyone knows her for, but I feel like not enough people know how gifted she was as a comedian and a writer. If you’re looking for more Carrie Fisher in your life, I suggest Postcards from the Edge (1990) which she wrote and is based loosely on her own relationship with her mother, and Soapdish (1991) where she plays a no-nonsense bitch named Betsy Faye Sharon. HERE. FOR. IT.

For a majority of the movie Jess and Marie listen to Harry and Sally gripe about the lack of love in their lives, inserting sassy responses and friendly advice when needed. However, one of my favourite scenes by far is when Harry tries to set Sally up with Jess, and Sally tries to set up Harry with Marie, and Jess and Marie find nothing in common with their dates, falling for each other instead. Not only is it hilarious but I love that the movie is giving a subtle wink to the audience and saying, “see? The only people Harry and Sally could possibly be suited for are each other. They belong together.”

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Credit: / Columbia Pictures

There’s so much to love about When Harry Met Sally… The effortless way they show the passage of time through simple wardrobe and hairstyling, the cute vignettes where elderly couples recount how they met each other, and the outstanding chemistry between the two leads. Seriously, the chemistry in this movie coupled with the amazingly conversational dialogue makes When Harry Met Sally… a movie that you need to pay close attention to. This is not a movie to have playing in the background. What really makes this movie worthwhile though, what makes it one of the most beloved romantic comedies in the genre, is how real it is. I tend to think that the strongest and most entertaining romances are the ones that are born out of friendship, and no movie better shows that evolution than When Harry Met Sally… Over the top romance stories are a lot of fun to watch, but it’s the ones you could actually imagine yourself in that tug at your heartstrings the hardest.

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Credit: / Columbia Pictures

If you’re looking for a romantic movie to watch with your significant other, or just a fun one to watch with your friends, I can’t recommend When Harry Met Sally… enough. Perfect for snuggling up on the couch with, let the movie’s messages of romance, friendship, and lightheartedness wash over you as you spend Valentine’s Day surrounded by the people you love.

Oh, and one more time just because I love it so much…”I’ll have what she’s having!”

What are your favourite rom-coms?

Let me know in the comments or on social media!

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