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Truly Lovable & Sentimental Movies Like When Harry Met Sally

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The sweetest movies to watch after When Harry Met Sally.

Movies like when harry met sally.
updated on:
September 25, 2023

When Harry Met Sally is one of the most beloved rom-coms of all time! It's funny, heartwarming, and nostalgic...It's the perfect recipe for an instant classic. I watched When Harry Met Sally for the first time last year (I know, super late to the game) and of course I couldn't help but fall in love with it. I bawled my eyes out at the end!

If you are a sucker for the friends to lovers trope, you will love it too. There's a reason When Harry Met Sally is on the top of everyone's list when fall comes around - this movie personifies autumn in New York. Here are the movies that come to my mind when I think of When Harry Met Sally. They are guaranteed to make you feel warm and fuzzy inside.

This post is all about movies like when harry met sally.

Where to watch When Harry Met Sally?

When Harry Met Sally (1989)

Watch on Amazon Prime Video

"It has a certain charm about it that will make you fall in love."

10 Things I Hate About You (1999)

Watch on Amazon Prime Video

"This has always been my comfort movie, I love Kat!!!"

Although 10 Things I Hate About You is more of an enemies to lovers trope, I think the playful banter between our two main characters is what really gives this story its charm. If When Harry Met Sally is an example of an 80s romance, 10 Things I Hate About You is definitely an example of an early 2000s romance.

The Princess Diaries 2: Royal Engagement (2004)

Watch on Amazon Prime Video

"Great follow up movie to the first one. Love the acting and its so adorable and heartwarming. Would totally recommend."

I know I can't stop recommending this movie, but it's because I don't hear people talking about it enough. This sequel to The Princess Diaries is as good as the first and Chris Pine's romance with Anne Hathaway feels so real, you can't help but fall for the two of them together.

Pillow Talk (1959)

Watch on Amazon Prime Video

"I have always loved this movie, so I can only say great things about it! Doris Day and Rock Hudson are great in this film. It is really good considering the age of it. Definitely recommend seeing it."

Pillow Talk is a movie I always recommend to people who haven't seen many "Old Hollywood" films. It's so cute it feels like it could have been made yesterday, but the set and costumes are so beautiful and classic, you won't be able to stop watching. Doris Day stars in the movie with Rock Hudson where the two of them share a phone line. Hilarious banter ensues between them and maybe even a budding romance.

27 Dresses (2008)

Watch on Amazon Prime Video

"Good throwback movie!"

If you're looking for a movie where the audience can see what the main character can't, 27 Dresses does just that. I mean, James Marsden is the obvious choice, Katherine Heigl!

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You've Got Mail (1998)

Watch on Amazon Prime Video

"I'm not sure if this will help anyone, but at least for entertainment's sake, here we go: this movie cast a spell on me."

This movie is one of my absolute favorites. It's part of the Meg Ryan rom-com trifecta, so you know I had to include it on here. It's about two "pen-pals" who chat over the internet and fall in love, but don't realize they are enemies in real life. It's set in NYC in the 90s and runs through all the seasons, so you'll get your doses of rom-com and fall vibes!

Sleepless in Seattle (1993)

Watch on Amazon Prime Video

"I’ve probably watched it over 20 times. I never get tired of it. It has a wonderful soundtrack."

I am one of those people who cannot resist Meg Ryan in a rom-com. Simple. But seriously, Sleepless in Seattle is really as good as people make it out to be. If you're wanting to watch all 3 iconic Meg Ryan films. start with When Harry Met Sally, then watch Sleepless in Seattle, and end with You've Got Mail. Now that's a Friday night I want to be a part of.

Autumn in New York (2000)

Watch on Amazon Prime Video

"This was a truly beautiful movie."

If you loved the fall city scenes in When Harry Met Sally, try this film. It stars Winona Ryder and Richard Gere and is about an older bachelor who falls for a young free spirit.

Viva Las Vegas (1964)

Watch on Amazon Prime Video

"Had to watch this classic film. It was really fun. You can feel the sparks fly."

This is one of my favorite Elvis films ever! It definitely has an enemies to lovers romance where the characters have a very playful and funny relationship. Plus, the music and dancing in this movie make it worth the watch!

My Best Friend's Wedding (1997)

Watch on Amazon Prime Video

"I saw this movie 4 times in theaters when it first came out. It is bubbly and joyful. Love the music. So many scenes are hysterical."

This movie stars Julia Roberts as a girl who realizes she is hopelessly in love with her best friend when he announces he is engaged to be married to someone else.

Clueless (1995)

Watch on Amazon Prime Video

"Always a great movie to watch! Funny and light hearted."

If you are a girl (like me) who lives and breathes for a friends to lovers trope - hence why I love When Harry Met Sally - Clueless will melt your heart. It's a modern retelling of Jane Austen's Emma, where our main character is completely oblivious to the fact that the love of her life is right in front of her the whole time!

How to Lose a Guy in 10 Days (2003)

Watch on Amazon Prime Video

"This is a great film! Lots of fun and cute. Matthew McConaughey is suave and adorable and Kate Hudson is cute and beautiful."

This movie is about a magazine editor and a marketing executive who make bets with their respective teams: one will make someone fall in love with them while the other will try to get someone to break up with them. They get paired up, which predictably causes its own kind of mayhem.

13 Going on 30 (2004)

Watch on Amazon Prime Video

"Great movie about growing up and learning to value those things we tend to not appreciate when young."

13 Going on 30 is one of those movies that will punch you in the gut but will always leave you with a happy ending. Jenna Rink wishes she was older and sophisticated but realizes when that wish comes true that it's not all it's cracked up to be. She learns if she stays true to herself she just might find love along the way.

If you like this post you may enjoy this post: 12 Fall Rom-Coms That Feel Like A Warm Pumpkin Pie

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Something's Gotta Give (2003)

Watch on Amazon Prime Video

"Great movie full of great actors and humor!"

Something's Gotta Give is a classic Nancy Meyers film filled with beautiful kitchens, nostalgic music, and an unexpected love story. What's not to love about that?

Crazy, Stupid Love (2011)

Watch on Amazon Prime Video

"One of my favorite movies. The writing is fantastic and the stacked cast really delivers."

Crazy, Stupid Love really has something for everybody. With lots of twists and turns, it parallels life's funny moments and reminds me a lot of When Harry Met Sally in that way.

Sweet Home Alabama (2002)

Watch on Amazon Prime Video

"This is one of my all-time favorite movies!"

Sweet Home Alabama is a friends to lovers to enemies back to lovers trope (LOL). It's about returning to your roots and rediscovering who you really are.

Emma (2020)

Watch on Amazon Prime Video

"The production values would have earned a 5-star rating all by themselves. But that would be to ignore the wonderful acting talent, the settings, the cinematography, the musical score, an everything else about it."

The way Jane Austen's Emma is played on a consistent loop in my head...The 2020 version in particular is so beautiful and will make you want to meddle in others' relationships so you can find your very own Mr. Knightley.


Do any movies come to your mind when asked for similar films to When Harry Met Sally? There are so many good ones that it's hard to list them all.

This post was all about best rom coms.

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