Long before pumpkin spice was even a twinkle in a marketing executive’s eye, there was You’ve Got Mail.
I’m so old vintage that I saw this movie at the cinema when it was released in 1998. I remember thinking it was alright… cute, fun. This casual attitude is best understood as a relic of the time – we just didn’t realise what a golden age of film we were living through. An incomplete list of the classics that came out around the same time: The Truman Show, The Big Lebowski, Fight Club, Sliding Doors, The Full Monty, The Fifth Element, Ten Things I Hate About You, and of course, the iconic beauty pageant satire Drop Dead Gorgeous with Kirsten Dunst, Amy Adams, and Brittany Murphy (in which a contestant’s mother gives sage advice: ‘if they ask you to take your top off, get the money first.’)
Legendary and highly quotable movies, no social media, no AI, no photographic evidence of any of the fun we had at house parties… as teens in the late 90s and early 2000s, we had it good.
So this was just your usual romcom fare, back then. Gorgeous, aspirational, but also ponderous and philosophical. Romantic, in a gentle, poetic way. Full of a fizzing, floaty feeling of things just beginning. A little eccentric. Featuring a city in the full bronze splendour of September. When there’s just that first whisp of cool air at the end of August I start thinking about watching this movie again. Let us count the ways that You’ve Got Mail remains an unmatched autumn comfort movie for the ages.
The outfits
It’s hard to describe how zietgiesty, how impossibly cool, the wisecracking, New-York big-coffees-with-our-friends lifestyle was at the time. The year that You’ve Got Mail came out, the very first UK Starbucks opened in London. 13-year-old me truly believed I would one day have an apartment just like Monica’s. And here was Meg Ryan, pottering around the big city in her outfits, with her lattes and her little bookstore. This girl loves a turtleneck. Even the little black dress that she wears to a party has a turtleneck. Wide leg trousers and little cardigans, crisp button downs, suede tunics and woolly tights, it’s all so comfortable, so feasible. Kathleen and her pumpkin is a timeless look.
Joe’s pick up lines
Ok, so there is one minor wrinkle in You’ve Got Mail, and that is the love interest, Joe. It’s hard to root for the central premise of the romcom to come true, and for mutual hostility to transform into love, because uuh, that guy is the worst. Kathleen’s boyfriend at the start of the movie, Frank, is miles better. He’s neurotic, and sees harbingers of doom everywhere, but at least he’s not an unrepentant capitalist ogre. Joe is smarmy. He’s self-congratulatory. You just know he doesn’t give a crap about the environment, or people in other countries (or zipcodes), as long as he can keep making money. Hindsight has somewhat softened my view of him, because I know – although he does not – that his big bookstore (the ‘theme park, multi-level, homogenize-the-world mochaccino land,’ as Kathleen calls it) will soon be eaten by a bigger monster, online shopping. And he does get one of the most romantic lines:
‘‘Don’t you love New York in the fall? It makes me wanna buy school supplies. I would send you a bouquet of newly sharpened pencils if I knew your name and address.’
The prophecies of Frank
Like Cassandra of Greek mythology, Frank’s tragedy is that he can foretell the future but is doomed never to be believed. He complains tetchily to Kathleen about the growing popularity of the internet: ‘you know what this is, you know what we’re seeing here? We’re seeing the end of Western civilisation as we know it.’ As prophetic cultural moments go, this one hurts in particular. Seeing that Kathleen has become obsessed by her new-fangled laptop computer, he warns her darkly, ‘you think this machine is your friend, but it’s not.’ He got it. Poor Frank. He was the only one who got it.
The city
This is the idealised, clean-living, brownstone New York of movies and sitcoms. The coping mechanism of choice is coffee. People spend on fancy bedsheets. Everyone is in some sort of relaxed, serious-but-not-too-serious relationship, everyone is competitively witty, and spreads out the weekend newspapers in bed on a Sunday morning. All this has a tender rosiness to it now, existing in a long-lost dream, just a few years before 9-11. Perhaps it is because I was too young to know too much, but I will always think of the ‘90s as a time of stability and a galvanising, workable hope for the future. ‘The end of history,’ was a phrase bandied about when I was a kid. I think a lot of us carry with us the too-perfect blue sky on that September morning in 2001, captured on camcorder video, in the just-before. We knew that place. There’s an exquisite wistfulness in returning, wrapped in a duvet, with a hot chocolate, to this old synthetic memory of a city.
Nora Ephron
Of course, this film was partly the work of that one-in-a-million mind, Nora Ephron. As well as You’ve Got Mail, she gifted us Sleepless in Seattle and When Harry Met Sally, and so much more. Her article about her favourite apartment is a lovely ode to ‘the caffeinated romance of the city that never sleeps’: Moving On, a Love Story | The New Yorker. Her commencement speech at Wellesley College in 1996 (1996 | Wellesley College) is one I recommend anyone read or listen to, if you’ve lost heart, and require encouragement. She tells the gals that life is hard, ‘but it’s also incredibly interesting,’ and ends with perhaps the greatest advice ever given to anyone, anywhere: ‘Be the heroine of your life, not the victim.’ This is a sentence I frequently tell myself when I’m freaking out about unimportant matters (and occasionally, important matters).
The wisdom of Nora, and this movie, and wearing pyjamas in the afternoon, and a caffeinated drink, and new school supplies: that is how to begin this season. Take heart.
Amy Jardine 
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