Pros & Cons of Watching When Harry Meets Sally 25 Years Too Late

Last month, I went to an outdoor screening of When Harry Met Sally. And believe it or not – it was my first time EVER seeing the movie. I’ll give you a minute to let that sink in. I kind of have a pop culture blind spot to a lot of classic films (I’m more of a TV person, if you couldn’t tell), and this is one of them. It’s particularly odd when I tell people this, because some of my favorite movies are of the rom-com genre, like Love Actually and Notting Hill #NoShame So going into my first viewing of WHMS, I had an inkling I would like it – I just didn’t realize I would like it THAT much. I couldn’t stop talking about it and thinking about it. I even looked up how much it would be on Amazon that same night. There are so many reasons why I enjoyed it, but I finally realized after viewing it why it had become such an important film in movie history – the story is timeless. At its core, WHMS is a movie questioning whether or not men and women can stay friends and never turn into lovers. That wasn’t just a problem in the 1980s, but it’s obviously still a question that’s asked today. And despite the fact WHMS is timeless, it’s not entirely “timeless”, as in, it’s been 25 years (to this day) since it was released, and there are still things that change over time. So here’s a few pros and cons I noted while watching this iconic movie for the very first time.

PRO: A youthful Meg Ryan

I think the first movie I ever saw Meg Ryan in was Sleepless in Seattle, which was made only four years after WHMS. But I don’t remember her ever looking as young as she did in this movie. I mean look at the youth! Look at the glow! She’s practically a baby acting out adult themes! It’s amazing that we can forever look back at this movie and seen the exact moment when she became a bonafide movie star.

CON: Meg Ryan’s face now

Well. Here she is. This picture was taken in April. Now 53, Meg is… still sporting a cute blonde ‘do.

PRO: Being grateful of escaping 80s fashion

Really, the fashion in this movie is the only thing that makes it distinguishable as a movie made in 1989, as opposed to present day. The script could be set in 2014, and nothing would have to be changed. Except for like the Rolodex and the phones. And especially the clothes. There are some scenes that scream 80s, including this one which features Meg Ryan wearing a stunning green velour dress with protruding shoulderpads as she serves as the maid of honor for her best friend’s wedding. Velour tho.

CON: Realizing that some of that 80s fashion is actually back in style

Could’ve sworn I saw a hipster wearing this same outfit in Silver Lake recently.

PRO: Understanding post-college life

Oh man. I so relate to this quote. I wouldn’t have been able to *get it* if I had watched it before. Even as a teenager I wouldn’t have completely understood.

“I’m 26 years old and I can’t even remember the name of the girl I was such good friends with that I wouldn’t even get involved with her boyfriend!”

CON: Self-realization of post-college life

Ugh. I’m 28. I graduated high school 10 years ago and I’m already starting to forget people I went to college with. Just put me in a senior living community now.

PRO: Still feeling hopeful for a love that lasts a lifetime

But how cute are these couples. Fun fact: they’re all real couples telling their real stories. Director Rob Reiner got the idea when he was talking to his producing friend’s dad and said, “Mr. Horn, how did you meet your wife?” Mr. Horn lit up and told Rob his story. And Mr. Horn is actually the very first guy featured in the set of interviews alongside his wife. *swoon*

CON: Wondering where the old couples are now

Okay sorry to be the downer here, but like, this movie was made 25 years ago, right? And these cute couples are old. Like they had already been married for about 50 years, old. I’m not (completely) delusional to realize that some of these folks might not be with us anymore and that makes me really sad.

PRO: The movie is a reminder Christmas in NYC is magical

New York City is the third biggest character in this movie. It should be When Harry Met Sally and We Met New York. Rob Reiner did a fantastic job of using the city as much as he could, making it look like a dream world where anything is possible – including love. The scenes that particularly hit me at the core were the ones during Christmas. Christmas is my favorite and even though I live in Los Angeles, I still yearn for White Christmases. When Harry and Sally are carrying that tree and establishing shots are shown of snow-covered landmarks in NY, it gives me all the warm and fuzzies.

CON: And then my dreams are dashed

Then I remember what living with freezing temps and bundling up in five+ layers and never-ending snow is like and I’m over it.

PRO: Appreciating the greatness that is Nora Ephron

I apologize for being such a bad comedy/writer nerd that I had no idea just how GOOD Nora Ephron’s writing was in this movie. Yes, the actors gave great performances and excellent delivery on lines that were just written on paper, but the way Nora Ephron writes is pure genius. She’s not just writing a script, she’s telling a story. It’s as if Harry Burns and Sally Albright are real life people, and Nora just transcribed their day to day conversations. Plus, her writing is smart and sentimental – it’s no wonder why so many movies and TV shows have followed in the same vain as WHMS – because it works.

PRO/CON: Retroactively having a crush on Billy Crystal

I’d like to think there’s a majority of people in my generation that associate Billy Crystal with SNL or Analyze This or City Slickers or the guy who hosts the Oscars a lot. We don’t necessarily think of him as the lead in a romantic comedy. So color me super surprised when I found myself crushing (?) on Billy Crystal (?!) throughout this movie!! He’s not even like, textbook Zefron handsome, but he’s funny and charming and boy is he in love with Sally. A man head over heels in love is worth swooning for.