One item from 'When Harry Met Sally' bonds Gen Z and Boomers, and it's probably not what you'd think
TikTokers branded it a "winter essential."

Billy Crystal wasn't the first in line to play Harry Burns in the 1989 rom-comWhen Harry Met Sally. Not by a long shot. In fact, director Rob Reiner considered Albert Brooks, Tom Hanks, Harrison Ford, Michael Keaton, Richard Dreyfuss, and Bill Murray for the part before him. Incidentally, according Business Insider, Albert Brooks thought it was too much like a "Woody Allen film," and Hanks believed it to be too "lightweight."
Crystal, who was best friends with Reiner, wound up exceeding expectations to pull out an iconic, grumpy performance that even the most cynical person could love.
- YouTubewww.youtube.com
Well, not everyone loved it. Just last year, a tweet went viral that revealed many Gen Z-ers had a real tough time with Billy Crystal as a leading man. And they weren't being especially shy about it. Emily Lefroy writes for Daily Mail, "The debate began after X user Zoe Rose Bryant responded to a post asking users to share the 'romcom scene that literally changed the trajectory of your life.'" Zoe then posted a clip from the Nora Ephron-penned classic and wrote, "You simply can't beat the blueprint."
The comment section disagreed, with many claiming Billy wasn't attractive enough for Meg Ryan's Sally. Ouch.
In the subreddit r/unpopularopinion, someone posted a similar sentiment claiming in part, "Harry's character is very unattractive, largely because he is a rude and condescending person. Sally is beautiful but annoying. The romantic scenes are cringy, mostly because Harry is such a jerk and so unappealing as a romantic lead."
This young Millennial writes, "I just tried to watch it for the first time (I'm 32), and I just couldn't do it. It's such a slog. I made it to right after they sleep together, and I had to stop it to take a break and watch something else… Harry is a d#$k and Sally just sucks."
They didn't like the deli orders either. "The way she places orders at restaurants isn't quirky, it's just awful." And they even had a note for the music composer: "Also, why is this movie so quiet? It might be an '80s thing, but the lack of a background score makes the scenes feel so awkward and cringe. I don't want to hear the click-clack of their shoes when they walk. And I certainly don't want to hear how wet their kissing is."
Meg Ryan sits at a diner in "When Harry Met Sally."Giphy
This Redditor agrees: "Honestly, I think it's a movie for Boomers who thought it was groundbreaking to show a man and a woman trying to be friends."
As if a Boomer just heard their name and perked up, they emphatically enter the chat, explaining, "The arrogant, self-centered character trait is the key issue! They’re young and dumb! Just like I was and practically everyone else I know when they were young. I’m in my sixties now. Young people mostly go through life with their heads shoved far up their a$es. Both sexes. It takes time and hard experience to pull their heads out. I don’t know if you’re young—don’t take this as a personal insult. But Harry is a spot-on portrayal of myself and Sally is my wife."
There's more. In a different thread entitled "What exactly is so amazing about When Harry Met Sally," a Millennial writes, "I watched it recently for the first time. I was born after it was released if that matters—if it was considered a movie of its time. I just don't really see the magic in it… I just don't really feel a yearning for Harry and Sally to fall in love."
This time, fellow Redditors really take the time to teach the OP, with one even including a character analysis for both Harry and Sally. Once the OP understands that Harry is like "this generation's Chandler Bing," they get a better overall grasp of the role, but still don't love the film.
@aoifeofarrell classic
One thing that does unite Gen Z with their older counterparts? Harry's sweater. Lydia Hawken writes for Mail Online that "TikTokers have rebranded the cable knit jumper (sweater) a 'winter essential.'"
Maybe we'll never prove that men and women can just be friends. But we do know that fashion trends can cross the generational aisle in the best of ways.