“It makes me want to buy new school supplies. I’d buy you a bouquet of newly sharpened pencils if I knew your name and address.” – the best movie ever (or maybe not, but one of my personal favorites, so pretty close to the best ever)

I feel like I talk about You’ve Got Mail too often, and I apologize, but it is my go-to “comfort” movie. You know how people have comfort foods? Chicken noodle soup, mashed potatoes, baked mac ‘n cheese — usually something not so good for your body, but perfect for your soul? That’s what “comfort” movies are. They might not be life-changing or Oscar-worthy, but they fill your insides with warm happiness and make you go back for seconds.
And usually you know the whole film’s script by heart. *raises hand*
I have seen You’ve Got Mail what must be at least 50 times since it came out in 1998, despite never having actually owned this film on VHS or DVD. I just borrow it from the library or rent it at least once a year, and retreat to my happy place. There is just so much to love about this movie! But for simplicity’s sake, I’ve narrowed it down to 10 reasons.
1. Meg Ryan’s character, Kathleen Kelley, owns the most adorable children’s book store. And her attitude about children and reading is just so great. “When you read a book as a child, it becomes a part of your identity in a way that no other reading in your whole life does.”
2. This is one of those movies that romanticizes New York, to borrow Woody Allen’s words, “all out of proportion.” And I love it! You can even see a nod to how unrealistically romanticized it is when Kathleen is opening up her shop at the beginning of the film and says, all love-struck, “Don’t you just love New York in the fall? Isn’t today just a beautiful day?” and in the background, a cab driver and another automobile driver are shouting their lungs out at one another. Just like the real New York.
It shows all the charming aspects of the city — the picturesque change of seasons, the cozily decorated shop windows, the bustling street fairs and farmers’ markets, the tiny cafes where you could meet the love of your life — and none of the grime or grit. The Upper West Side, where the story takes place, is truly lovely. Those brownstones!
3. Having now lived in the city for more than a year, it’s fun to spot New York institutions that are still around and seen in the movie. There’s H&H Bagels, Grey’s Papaya, and Cafe Lalo, for starters. It’s also very true to life that even though it’s easy to hate on corporate coffee like Starbucks, everyone seems to go there before work (isn’t it ironic that Kathleen is so bent out of shape about megachain Fox Books moving into the neighborhood, but happily pays for an overpriced Starbucks latte?). I don’t go to Starbucks often, but when I do, it’s usually a block from my office, and I always run into one of my co-workers.
“The whole purpose of places like Starbucks is for people with no decision-making ability whatsoever to make six decisions just to buy one cup of coffee. Short, tall, light, dark, caf, decaf, low-fat, non-fat, etc. So people who don’t know what the hell they’re doing or who on earth they are, can, for only $2.95, get not just a cup of coffee, but an absolutely defining sense of self. Tall! Decaf! Cappuccino!”
(I’m either a tall, skinny dirty chai latte or a tall blonde coffee, black. Coffee orders sound kind of like you are ordering up people. Don’t think about it too much.)
4. I adore the nods to Pride and Prejudice in the story. It’s not just that the characters discuss the book (or that it is one of my favorites), it’s that their feud-turned-romance parallels the story of Darcy and Elizabeth, right down to their contrasting socioeconomic classes and lifestyles. The movie is also a nod to the black-and-white holiday film The Shop Around the Corner, in which two shop associates unknowingly pen love letters to one another. So that’s cute.
5. Meg Ryan’s character’s adorable, shabby chic apartment! Her adorably simple and monochrome wardrobe! I’m pretty sure this fictional character is responsible for my lifelong obsession with cardigans and a brief stint with turtlenecks, too. Did I mention her adorable children’s bookstore? So much adorable!
6. Tom Hanks in this movie is just so impossibly charming. When I think of Tom Hanks, I usually think of him as a “dad” figure because I’ve grown up with him as an actor and he’s done some kids’ movies, and honestly, he’s not the stereotypical hunky Hollywood romantic lead. He’s got that goofy curly hair and the big laugh, but Nora Ephron’s dialogue just makes him impossible not to like!
I mean, that line! The heartbreaking line. You know the one. “Well… if I hadn’t been Fox Books and you hadn’t been The Shop Around the Corner, and you and I had just, well, met… I would have asked for your number, and I wouldn’t have been able to wait twenty-four hours before calling you and saying, ‘Hey, how about… oh, how about some coffee or, you know, drinks or dinner or a movie… for as long as we both shall live?'” Hello! Marry him. Marry him right now, Kathleen Kelley. You could totally see falling for his character via email, and then just deciding once you meet him that the goofy hair isn’t so bad. Also, I hear the guy does a great Woody the Cowboy impression.
7. I love how outdated all the technology in this movie is now. Dial-up internet! AOL Instant Messenger! Macbooks that could double as door stops! People sitting at home waiting for their land lines to ring! References to VCRs! The next time you watch this movie, pay special attention to the fact that the only two programs Kathleen and Joe appear to have on their laptops is a shortcut to email and another to AOL’s strangely primitive form of “the Internet.” No word processing programs, no Solitaire. Nothing else. That really makes me laugh.
8. Also some of the New York stuff is outdated, too. Mainly the great line from Christina, the 20-something sales associate at The Shop Around the Corner: “If we fold, I won’t be able to find a new part-time job. And then I won’t be able to afford my rent, and I’ll have to move! To Brooklyn!” Said with much horror. Brooklyn is where all the cool kids go these days, Christina. And it’s actually becoming more expensive to live there at a faster rate than Manhattan. Who would’ve thunk?

9. Speaking of Brooklyn, I’m pretty sure Kathleen’s boyfriend in this movie is the original hipster. Here he is with a typewriter! No laptops for George! He here is celebrating the virtues of radio over television! Here he is using phrases like “Jeffersonian purity” to describe independent businesses! Here he is fearful of dating Republicans! I bet he lives in Williamsburg these days.
10. The ending to this movie is just so perfect. Not to spoil it for you or anything, but it is a rom-com, and *big gasp* THE TWO MAIN CHARACTERS END UP TOGETHER. And no other movie’s ending makes me feel quite so warm and fuzzy inside except for maybe the end of Breakfast at Tiffany’s because not only do Holly Golightly and Paul Varjak kiss in the rain, Holly also recovers her lost cat, Cat, from the dumpster in the alley. This ending mainly moves me because I find it very upsetting that she would disown her cat and throw him out into the alley, so I am deeply relieved when she finds him again. (Oh, by the way, there are no alleys in Manhattan!!! Way to go, Hollywood writers.)
Anyway, the ending to You’ve Got Mail involves a dog, so it’s also a winner.

Do you have a favorite movie you could watch again and again? Even if you know it isn’t exactly a “good” movie, per say?
I’m also a huge sucker for the Little Women version with Winona Ryder and Susan Sarandon. I especially love Christian Bale in it as Laurie, a fact that disgusts most young men in my life, who prefer to think of him only as Batman these days.