6+ Thoughts I Had Watching When Harry Met Sally For The First Time

Meg Ryan and Billy Crystal in When Harry Met Sally
(Image credit: Castle Rock Entertainment)

I consider myself a romantic comedy connoisseur. I have seen so many, from major blockbusters to indie favorites to ones that no one seems to have seen but me. It’s one of my favorite genres.  You would think because I love this type of movie so much that I have seen every major romantic comedy out there. However, some of the most popular ones I haven't watched, including the famous one starring Billy Crystal and Meg Ryan. I have never seen When Harry Met Sally, or if I have, I have no recollection of ever watching it.  

You would think I would have watched it many times, because I adore Meg Ryan movies, especially her romantic comedies, and I know many consider this one of the best romantic comedies of all time. But, nope, I didn’t know what happened When Harry Met Sally.  

 Now I know, and I have some thoughts. 

Meg Ryan and Billy Crystal in When Harry Met Sally

(Image credit: Castle Rock Entertainment)

Do I Like Opposites Attract Rom-Coms? 

This is probably one of the most obvious opposites attract films I have ever seen. This made me wonder: Wait, are any of my favorite romantic comedies in that category?

Not a romantic comedy, but Katniss and Peeta are definitely one of my favorite book couples that fit into that category, the same with many of Nicholas Sparks’ romantic movie couples that I love, but what about romantic comedies? I think Clueless may be one of the few of my favorite that neatly fits into the opposites attract category.

Seeing how well the trope works in When Harry Met Sally made me want to see more of those types of rom-coms. There are plenty of great enemies to-lovers movies, but that's not the same. This film may be one of the best versions of this type of romantic movie, and maybe it’s time for the genre to add more of them, or maybe I need to find and watch more of them. 

Either way, I want more opposites attract rom-coms.

Meg Ryan and Billy Crystal in When Harry Met Sally

(Image credit: Castle Rock Entertainment)

The Makeup And Costumes In When Harry Met Sally Are Great 

Over the course of the movie’s 12-year period, I am completely sold that they are in their early 20s to early 30s. I give credit to the costume and makeup department for making the age transition believable. I also applaud them for capturing the decade with their clothing and makeup choices.

As stated, I have seen so many Meg Ryan movies, but I think this is the first one where I kept thinking “I love her outfit.” Sally is definitely a movie fashion icon. We don’t talk about her wardrobe enough as a society.

Billy Crystal and Carrie Fisher in When Harry Met Sally

(Image credit: Castle Rock Entertainment)

There Are So Many Famous People That I Didn't Know Were Associated With This Film 

I only know that Nora Ephron is associated with this movie because I love her movies, including Sleepless in Seattle and all its Christmasness. Therefore, I am constantly trying to make it through her filmography, but just kept putting off When Harry Met Sally

I also had no clue how she was tied to this film. Now I know she was a producer on it and wrote the script. The opening credits also let me know that it was directed by Rob Reiner. I had no idea this was one of his movies.

I also learned that Harry Connick Jr. was established enough in his career in the '80s to be part of the soundtrack and music arrangement. Additionally, I didn't know that Carrie Fisher was in it. She was one of the best parts of the movie, and it’s definitely one of her roles worth watching.

The team in front and behind the camera really help make this a memorable film.

Billy Crystal and Meg Ryan in When Harry Met Sally

(Image credit: Castle Rock Entertainment)

The Couples Talking To The Camera Section May Be My Favorite Part Of When Harry Met Sally

The short segments that have couples talking about their love stories are just so charming. Each couple had an entertaining story. It’s also just a reminder of how almost everyone has a unique love story, both fictional (like these couples) and real couples.

Every couple also has a compelling story. Even something as simple as a grocery store meeting can be fascinating when you learn more context, details, and more of the evolution of the relationship. I also loved how it comes full circle with Harry and Sally speaking about their relationship at the end. It contextualizes those couple scenes and gives them more of a purpose. 

Billy Crystal and Meg Ryan in When Harry Met Sally

(Image credit: Castle Rock Entertainment)

The "I'm Sorry" Scene May Be The Film's Best Declaration Of Love 

When Harry Met Sally is for people who like talking. It’s very much a movie where conversations are Harry and Sally’s love language. There aren’t many big romantic gestures, but small ones. This may make it a rom-com that's more grounded in reality than most, but I still like my big gestures — unrealistic or not.

One of the film’s best small gesture moments is after Harry and Sally get into a big fight. Harry asks to say something and then apologizes and hugs her. This is such a big moment and character development for him.

The Harry we get to know is very confident in always being right. He will shout his wrongness just to hear his own voice. Therefore, when he doesn’t continue to fight and try to prove his point, it shows how much he loves her. Not losing or hurting her is more important to him than continuing to argue.

Harry saying he’s sorry doesn’t seem like something that happens often. It’s with those simple words that you know he loves her and needs her. He loves her a lot

Billy Crystal and Meg Ryan in When Harry Met Sally

(Image credit: Castle Rock Entertainment)

I Preferred Harry And Sally As Just Friends 

One of the reasons I delayed watching When Harry Met Sally is because, for a long time, I believed it wasn’t the typical romantic comedy. I thought it was one about platonic friendship. I expected Harry and Sally to not end up together but be soulmates in the friendship way, and help each other find romantic love with other people. 

One day, I found out that my belief was wrong. They end up together. I really liked my idea, so I lost interest in seeing the movie. Obviously, my idea is likely not going to make romantic comedy fans happy, especially those who want to see the characters end up together.

I respect that, but I wanted what I wanted. I still think the friend idea would have been really interesting and show that men and women can actually be friends. They can also be non-romantic soulmates. However, I did really enjoy Harry’s final declaration to Sally. It is the film’s biggest romantic gesture. I also liked seeing them happily talk about their love story and wedding at the end. 

I also did enjoy what the film had to say about love and relationships. It's a sweet idea that sometimes people fall for their best friend, and the concept of the right person at the wrong time rings true. 

Carrie Fisher and Bruno Kirby in When Harry Met Sally

(Image credit: Castle Rock Entertainment)

Other Thoughts 

We still have other stuff to discuss about When Harry Met Sally, besides whether I should make dressing like Sally my whole personality from now on. 

  • I would have paid a lot of money to see a Jess (Bruno Kirby) and Marie (Carrie Fisher) spin-off movie. I really enjoyed their relationship and love story.
  • The last names Albright and Burns are such a fun obvious note to their opposite personalities and also how they fit.
  • For a moment, I was hoping this was about to be one of those set in Chicago movies. I was disappointed when it turned into another one of those movies set in New York. 
  • Talking to (texting) a friend while you watch a movie together from separate homes is very relatable. 
  • Harry may have one of the best movie developments and emotional glow ups. I went from finding him annoying to enjoying him by the end. 
  • I loved that it’s a film about 30-somethings who really experience life before finally finding their soulmates. That seems somehow revolutionary in the world of romantic comedies.

This is definitely one of the best Billy Crystal movies along with being one of the best Meg Ryan ones. It’s not one of my favorite romantic comedies, but I am glad I finally watched it. I also now understand why people adore it so much. 

Rent/buy When Harry Met Sally on Amazon. 

Jerrica Tisdale
Freelance Writer

Spent most of my life in various parts of Illinois, including attending college in Evanston. I have been a life long lover of pop culture, especially television, turned that passion into writing about all things entertainment related. When I'm not writing about pop culture, I can be found channeling Gordon Ramsay by kicking people out the kitchen.