We Showed 'You've Got Mail' to Our Gen-Z Coworkers and Now Feel Very Old

Though it's still a classic after 20 years, there are definitely some things that don't hold up.

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(Image credit: Morgan McMullen)

Its portrayal of logging onto the internetThe look and feel of New York and its apartmentsThe role of bookstoresHow characters interact with technologyHow Tom Hanks basically catfished Kathleen for the second half of the movie

This year, the beloved romantic comedy You’ve Got Mail celebrates its 20th anniversary. If realizing that 1998 was two decades ago makes you feel old, you’re really not going to like what our Generation Z colleagues had to say about this film when we asked them to watch it.

For the uninitated, You've Got Mail was directed by Nora Ephron, with a screenplay by Ephron and her sister, Delia. The movie is a send-up of the 1940s romance by Ernst Lubitsch, The Shop Around the Corner, in which two rival co-workers turn out to be one another’s adored pen pals. In the Ephron version, Meg Ryan plays Kathleen, the owner of a small children’s bookstore called (naturally) The Shop Around the Corner, which she inherited from her deceased mother and which is at risk of closure, thanks to the opening of a Fox Books Megastore. If the idea of a big, scary bookstore of all things isn’t quaint enough in 2018, Kathleen is also enamored with her pen (keyboard?) pal, someone she met in a chat-room who goes by the handle NY152. Little does she know, NY152 is actually Joe Fox (a.k.a Tom Hanks, at Peak Sexy Dad), the mega-rich owner of Fox Books.

It’s a beautiful movie—a real classic rom-com—and despite its tech-talk seeming a little dated, the millennials in the room who recall seeing You've Got Mail in theaters think it holds up surprisingly well.

But because we might be a bit biased (the two of us literally have this movie memorized, you can test us), we decided to assign a viewing of the movie to three of our Gen-Z coworkers—Ruby Buddemeyer, Zoe Harris, and Rachel Epstein—to see if You’ve Got Mail actually stands the test of time.

Here’s what they had to say about some of the movie’s key scenes (and what we, as millennials, think about what they thought):

Its portrayal of logging onto the internet

RUBY BUDDEMEYER: I recognize the sound of the PC booting up in the credits, but it doesn’t necessarily make me feel nostalgic. We had an old, '90s-era PC in my house growing up, but I wasn’t really an avid computer user at the time. My early computer memories are of my dad’s iBook (we had the orange one).

ZOE HARRIS: At the beginning, the transition from the Warner Brothers logo on the screen to the computer—with the ferociously-typing keyboard noises, the beeps and boops of the computer—was so charming.

RACHEL EPSTEIN: I’m on the Gen-Y/Gen-Z cusp, so I grew up with dial-up. I first taught myself how to use our clunky HP desktop at the age of six, and my dad and I still jokingly say, “You’ve got mail!” in that iconic, robotic voice because we clearly logged on to AOL too much in the house growing up.

ZH: The computer's desktop screen with a closed folder, a folder with a file in it, a recycling bin, and a tiny icon of a desktop computer?! Who drew these little icon things? Then it says, without being prompted, "You've got mail!" Is a computer allowed to talk to you if you don't ask it to?


DANIELLE MCNALLY: As Kathleen Kelly so eloquently describes the feelings surrounding email in the 1990s: “I turn on my computer. I wait impatiently as it connects. I go online, and my breath catches in my chest until I hear three little words: 'You’ve got mail.'” I vividly remember that suspense. Did my crush email me? Will he be ::gasp:: online right now and I can AOL Instant Messenger with him? To be coming of age while internet communication was coming of age... It was a distinct experience that only a tween getting to communicate with her peers outside of the watchful eyes (and ears) of her parents and siblings can understand.

CADY DRELL: Agreed. I had an entire AIM life in a way that even the connectedness of today can't really compare to. It was so anonymous. But I wasn't allowed in chat rooms. Also I remember when I saw this in theaters and my parents had just updated our version of AOL (we were always behind because it took what seemed like a thousand years) and the one in this movie was our old version and I found myself missing it. Ah, the old timey internet.

The look and feel of New York and its apartments

ZH: Fox Books is representative of the big, mean capitalist coming in and stealing customers from a smaller bookstore. Gentrification now looks a lot different and less charming. Book business feuds! Nothing compared to the tech gentrification we see now.

RB: I immediately recognize that New York trope of being so, so busy in the first scenes with Tom Hank’s girlfriend. It seems a little dated and cheesy as hell but, like, it works. And honestly, that’s how I feel about the movie as a whole.

RE: How does Kathleen afford such a big apartment in NYC when her entire store only makes $350,000 a year?!

ZH: When The Shop Around the Corner might have to close and the youngest employee says she might not be able to pay her rent so she'll have to move, “To Brooklyn!”—apparently Brooklyn didn't have the same hyper-expensive, gentrified, hipster allure it does now.

RB: My favorite characters are definitely Kathleen’s two young co-workers. I’m trying to think of who they would be in 2018. I’m envisioning them as douchey hipsters who work at McNally Jackson.


DM: George definitely led me astray with his line, “The joy of rent control: Six rooms, $450 a month." When I moved to NYC a decade ago, I was like, Oh, I'll just find a rent-controlled apartment. LOL. Then I forked over $1,250 a month for my share of a studio-turned-two-bedroom on the sixth floor of a walk-up.

CD: Kathleen's sunny, book-filled home is basically apartment porn, and it seems so adorably unrealistic to me now. I don't think it's even a symptom of the year the movie was created as much as it is my coming into adulthood and realizing that having white linen sheets is an extreme pain in the ass not worth undertaking. This is like Nancy Meyers–level set design, though. Nora Ephron had impeccable taste and I miss her.

The role of bookstores

RE: I’m a pretty nostalgic person in general, but I found myself really nostalgic while watching this movie. Maybe it was the whole premise of having a movie centered around a bookstore. God, I love bookstores.

ZH: When offered a movie, the kids instead veered into a bookshop to watch a woman in a princess hat read aloud to a crowd. I hope this is a decision my kids will make in 15 years.

RB: It’s sad watching this in 2018, knowing the fate of the book industry: That independent bookstores and corporate, discount booksellers alike were crushed by e-readers and the digital world. It’s interesting that the rise of technology is such an important part of the movie yet that potential outcome isn’t really on any of the character’s minds? Maybe Kathleen’s boyfriend thought about it a bit.

ZH: I wish an independent bookstore (seemingly of only children's books and stuffed animals) could take up that much physical space in NYC real estate and employ that many people at once.


CD: How the tables have turned. Now, when I pass a Barnes & Noble (the IRL Fox Books) and it's miraculously still in business, I think, Good for them!

DM: I recently stumbled across a brick-and-mortar Amazon Books store just a few blocks south of where YGM is set, so maybe everything is coming back around and there's hope for independent booksellers yet...?!

CD: I hope you're right. Mainly because Book Smell remains one of the top 10 best smells.

How characters interact with technology

RB: Little lines like Kathleen’s co-workers asking each other if “they’re online” are really funny to me. Since computers were already becoming the norm during my childhood, I never had or even really heard conversations like that.

ZH: Tom Hanks can't just hold down the “Delete” button, but needs to click it repeatedly to delete an entire phrase. Click. Click. Click. Until the entire sentence is gone.

RE: Obsessed with the Shopgirl screen name. My first screen name was SportsGirl302. The 302 stood in for 2003, a.k.a. when the Marlins won the World Series—very smart, I know.

ZH: As I watch Frank type a couple lines of poetry on a piece of paper, take it directly out of the typewriter, and hand it to Kathleen, it makes me want a typewriter of my own for the times when the printer doesn't work. And I've just always loved typewriters.


DM: I fully understand Frank's disdain for the computer and affection for the typewriter. I have felt that way about each new communication-related technological evolution: “Ugh. But what am I going to do without Blackberry messenger?” “Slack is way too overwhelming.” “What is this newfangled thing the kids call Snapchat?” I think people will always yearn for what they know and are comfortable with.

CD: Eh, Frank was pretentious. But I also like that people know he's pretentious in the story. Kathleen was too good for him. That said, I got the first generation iPhone for my birthday when I was about to go to college and remember being so perplexed by it that I kept it in the box for a few weeks. Now my phone is my family, but I think rapid technological advancement takes some getting used to.

How Tom Hanks basically catfished Kathleen for the second half of the movie

RE: I was pretty shocked at how much time Joe and Kathleen spent together before Joe told her who he really was. I feel like that would not fly if this movie was made again today. People would think he’s a liar and leading her on.

RB: The concept of meeting in a chatroom doesn’t feel too dated to me. I had AIM in my early teens, so it’s not a totally foreign concept. I’m not at all watching this thinking it feels incredibly old or anything. Though I keep thinking of the plot in 2018 standards, like that Hanks and Ryan would meet on Tinder or Bumble.

ZH: This method of meeting a significant other is like rustic, extremely lucky Tinder with no pictures. How likely is it that they would meet the perfect person—without much fear that meeting would be dangerous or creepy—and fall in love with them from an email exchange? Lucky! And the part when Joe is outside the cafe trying to see if Shopgirl is beautiful? Now, with online dating and the constant exposure to pictures and digital media, knowing whether the person was beautiful would be the first thing he’d know.


(Image credit: Ronald Siemoneit)

RE: Kathleen had to have known the whole time it was him, but we can continue to pretend she didn’t.


DM: I remember meeting people in chatrooms (“A/S/L?” anyone?), and it was super titillating until To Catch a Predator came out and parents shut that ish down. Kind of interesting that chat rooms fell away in the early aughts and it was almost a decade before dating apps really became a thing. How did people find dates? I guess there was Match.com...

CD: Oh man, I was such a little catfish when I was growing up on the 'net.

DM: One thing that definitely holds up: Kathleen and her co-workers running through all the potential reasons Joe didn't show (besides, you know, just being an asshole who's not that into her). Who among us hasn't consoled a friend who was ghosted by saying that her crush is potentially a serial killer?

CD: I think that gets at the heart of why this movie ultimately holds up. There's a line in another excellent Nora Ephron-penned film, Sleepless in Seattle, where Meg Ryan's character is talking to her friend about the woman she suspects is Tom Hanks' girlfriend (but is actually just a friend). She tries to badmouth her but then just says, "Honestly, she looks like someone we would be friends with." Every character in this movie is a little bit like someone you'd be friends with. It's how you can still root for Tom Hanks, even though he's a ruthless capitalist.

DM: Still, with 2018's hindsight, the premise is pretty creepy. (Though there's no way this premise could happen in 2018. Thanks, Google!) But also the premise is what makes the whole thing so freaking charming. That Joe has a project that needs “T-W-E-A-K-I-N-G,” i.e. making her fall in love with him. I mean, swoon.

Cady Drell

Cady Drell is a writer, editor, researcher and pet enthusiast from Brooklyn.