25 Life Lessons Learned From 'When Harry Met Sally'

On Monday, July 21, Rob Reiner's romantic comedy classic When Harry Met Sally celebrates its 25th anniversary. That's 25 years of moviegoers asking the question made famous by When Harry Met Sally's scribe Nora Ephron: "Can men and women just be friends?"

Since its release, the movie — which is a heartfelt and painfully funny love letter to love, friendship, and, yes, New York City — has become not only the gold standard for romcoms, but the go-to reference for any relationship that started as a friendship and eventually evolved into something more.

Starring Billy Crystal and Meg Ryan as the titular Harry and Sally, the years-spanning story is an on-the-nose assessment of relationships in your 20s and 30s connected with audiences and critics in 1989 (it made $92 million in theaters, has an 88 percent certified fresh rating on Rotten Tomatoes) and it still does. If you've ever been platonic friends with someone of the opposite sex or you're just a movie buff (or both), When Harry Met Sally has, no doubt, been a big part of your life.

Despite some very '80s fashion choices and the absence of modern technology, When Harry Met Sally feels as relevant and fresh as it was in 1989. This keen, hilarious observation on the complicated dynamics of male/female friendships has taught us a lot over 25 years, and in honor of Harry and Sally's silver anniversary, here are some of their best lessons.

1. Men and Women Can Just Be Friends

Now, hear me out on this one. Yes, Harry and Sally do eventually wind up together, but you know what they were for a really long time? Just friends. Men and women can definitely just be friends, but a lucky few, like Harry and Sally, may just fall in love with theirs.

2. Men and Women Can Just Be Friends... But You Will Always Wonder

Harry goes on a long, famous diatribe about all the reasons why men and women can't just be friends, in which he argues that sex always gets in the way. Even if you're not necessarily attracted to your friend, you will, at one time or another, wonder what a romantic evening (or lifetime) with them would be like. But nine times out of ten you realize that sex will probably ruin it and you just go back to marathoning Netflix together.

3. "Surrey With a Fringe On Top" is the Most Embarrassing Song You Could Be Singing When You Run Into Your Ex and Their New Beau

Oh, forget you Helen and Ira.

4. New York Looks the Most Beautiful in the Spring... No, Winter... Nope, Autumn

Their walk in Central Park in the fall looks like something, well, out of a movie.

5. Women Can, and Sometimes Do, Fake Orgasms

Yes, yes, yes.

6. There is Nothing Worse Than a Bad Setup

Harry was not compatible with Marie, nor Sally with Jess. Their forced banter was a reminder that just because you're single and they're single doesn't mean you should be setup.

7. New Year's Eve Gives You Unrealistic Expectations

You're either miserable at a party or miserable at home eating Mallomars. Either way, you're just miserable...until your best friend confesses their love to you.

8. You Should Never Take Anyone You're Dating to the Airport

Eventually they are going to ask you why you don't take them to the airport anymore. Harry may have been a curmudgeon, but he got a lot of things right.

9. Wagon Wheel Coffee Tables Are Really Ugly

Sorry, Jess.

10. No Matter How You Met, or How You Fell in (and Sometimes Out of) Love, There's Nothing More Romantic Than Growing Old With Someone

Justin Girdler on YouTube

The interviews with all of the old couples spliced throughout the movie are the best.

11. When You're At a Restaurant, Don't Be Embarrassed to Order Your Dish to Your Very Specific Liking

"On the side is very important to you." (Just maybe tip the waitress or waiter a little bit more.)

12. Even When You're Horrifically Depressed, You Still Have to Participate in The Wave

The New York Giants are depending on it, Harry.

13. Even If You Didn't Want To Marry Your Significant Other, Hearing That They Are Marrying Their Rebound Will Destroy You

Especially if they are paralegals named Kimberly. She's not supposed to be the one.

14. Men and Women Have Very Different Opinions on the End of Casablanca

A lifetime of great sex or being practical? The debate still continues.

15. If You Do Wind Up Sleeping With Your Best Friend, For the Love of God, Don't Take Off First Thing in the Morning and Act Like Nothing Happened

Otherwise you're going to risk losing them and endure a whole lot of lonely montages.

16. If You're Going to Finally Tell Someone How You Feel About Them, Don't Hold Back

"I came here tonight because when you realize you want to spend the rest of your life with somebody, you want the rest of your life to start as soon as possible." That's a damn good line if there ever was one.

17. If You Have a Dark Side, Someone With a Light Side Will Balance You Out

Like, so dark you read the end of books in case you die before you can finish it. Yeah, you need someone peppy.

18. Everyone Has Weird Sex Dreams

Harry's recurring dream involved being judged at the Olympics for his lovemaking techniques in which one of the judges is his mother. Makes you feel better about your weird sex dreams, no?

19. The Real Real Estate Section in New York is the Obituaries

"Mr. Kline died yesterday, leaving behind a wife, two children, and a spacious three bedroom apartment with a wood-burning fireplace."

20. Sheldons Are For Doing Your Taxes and Root Canals, Not "Humpin' and Pumpin'"

Sorry, Sheldons.

21. They Don't Make Sundays for Days of the Week Underpants

Because of God.

22. Everyone is Terrible at Pictionary, Both the Players Drawing and the Players Guessing


23. If You're Seeing a Married Person, They Are Never Going to Leave Their Spouse For You

"He's never gonna leave her, is he?" Nope.

24. If You Hate Someone At First, There's a Good Chance You're Going To Hook Up With Them At Some Point

The law of romcom.

25. Sometimes It Takes Three Months, or Sometimes It Takes 12 Years and Three Months, But You'll Know When It's Right

And, sometimes, if you're very lucky, that person just so happens to be your best friend.

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