As someone who loves romantic comedies, I have never come across one that gives such a raw and real insight into relationships as “When Harry Met Sally” does.
Adapted from a screenplay written by Nora Ephron and directed by Rob Reiner, it was praised for its insight into relationships and was nominated for an Academy Award for Best Original Screenplay.
Starring Billy Crystal as Harry Burns and Meg Ryan as Sally Albright, the rom-com came out in 1989 and made over $92.8 million at the North American box office.
“When Harry Met Sally” follows a man and a woman who, over twelve years, keep coincidentally bumping into each other and trying to navigate the question, “Can men and women ever just be friends?”
Unlike most romantic comedies that rush love or rely on dramatic and outgoing gestures, “When Harry Met Sally” takes its time showing how real relationships grow into something more and how natural it happens.
Harry and Sally’s relationship is not built on whims and sudden realizations. Their relationship is built on years of friendship, arguments, understanding, and vulnerability: traits that make real relationships work.

The movie starts with Harry and Sally riding together from college to New York, where they immediately clash. By the end of the road trip, they decide they can not be friends because he is cynical and believes that men and women can not be friends since “the sex part always gets in the way,” while she completely disagrees.
After many run-ins over the years, they finally decide they’re in a place to be friends. Both have grown separately as individuals through breakups and divorce. Taking them into a deep platonic friendship, which makes it feel earned.
Things get complicated when Harry comes over to comfort Sally after a rough night, and what turns into comfort turns into intimacy. Forcing them to answer the question they have debated for years, “Can men and women ever just be friends?”
We get the answer the next morning when Harry leaves abruptly, and they both call it a mistake, even though it is clear it was more than that.
One of the turning points in the film comes when Sally takes control of her worth. When Harry calls, hoping to smooth things over and still be each other’s New Year’s Eve date, she refuses, telling him she is not his consolation prize and hangs up.
The movie ends with Harry alone on New Year’s Eve, realizing that he loves Sally and wants to be with her. He rushes to find her and delivers arguably the best monologue in any romantic comedy.

The friendships and relationships explored throughout the movie made me reflect on my own.
The first time I watched this movie was on one of my mom and I’s rom-com movie days, where we each picked a movie we had been wanting to see.
I had always heard “When Harry Met Sally” was a classic, but I never heard many people talk about it. After watching, I realized it is severely underrated and doesn’t get the recognition it deserves.
Not only are the story and the relationship dynamics realistic, but the way the film is shot feels intimate. The music also adds a timeless feel.
The use of Frank Sinatra’s “It Had To Be You” sums it up perfectly. Showing viewers that love is truly knowing someone.
Needless to say, this film is the most real representation of love I have ever seen on a screen, which is why it ranks first on my top romantic comedies of all time list.

Megan • Nov 14, 2025 at 1:52 PM
I have never watch “When Harry Met Sally” but after reading this article it really makes me want to watch it. Khloe did a wonderful job!!
Michael Woodard • Nov 14, 2025 at 12:36 PM
Well worded Khloe! Love the way you critique!
Kayla • Nov 14, 2025 at 10:36 AM
Wow, i’ve never seen this film but your opinion has me curious watch it! I love the “realness” you’re describing in it. Thank you for sharing 🙂
Kori Stewart • Nov 14, 2025 at 9:58 AM
I love this movie! One of my favorites. Amazing article! I hope you review more movies!!!