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upper west side view

Of all the late-nineties rom-coms featuring plucky heroines, adorable New York apartments and lives full of utter charm, You’ve Got Mail might be my favorite.

I saw it in the theater as a teenager, and have watched it countless times since – with my family, my girlfriends, by myself. I remember the days of dial-up AOL and the magic of finding new friends online before social media, though I am about 15 years younger than Kathleen Kelly. I once spent a weekend on the Upper West Side visiting some of the movie’s iconic locations: Cafe Lalo, Zabar’s, Gray’s Papaya, the 91st Street Garden in Riverside Park. (I did not see Joe and Brinkley, but you can bet I looked.) I still have the soundtrack on CD, and New York in the fall definitely makes me want to buy school supplies.

You’ve Got Mail continues to charm me for so many reasons: the witty, perfectly timed dialogue; the cozy bookshop packed with beloved children’s classics and kind employees; the epistolary love story (though I have thoughts, these days, about Joe Fox and his personal ethics). But the more time I spend with it, the more clearly I see what my friend Kari noted years ago: in addition to a classic romantic comedy, it is (in Kari’s words) “a moving portrait of a woman who is going through a crisis of vocation.”

Kathleen has always known she’d run The Shop Around the Corner; she started helping her mother there after school at age six, and never left. We don’t even know if she went to college, or entertained other dreams for her life. She has grown up shaped by this bookstore and this neighborhood, and she would happily go on selling children’s books there forever. But she is not given that choice: Fox Books moves in across the way, and its big-box appeal (coupled, no doubt, with rising rents and the lurking shadow of Amazon) forces Kathleen to make a decision she never foresaw: “Close. We’re going to close.”

I’ve thought about Kathleen a lot this past year, as the pandemic has upended so many of the jobs most of us believed would bring us stability and security. I was furloughed from my higher ed job last May, then finally laid off in January after months of waiting. This wasn’t the first time, though: my last few years in higher ed have been marked by uncertainty and change, including two previous layoffs and a few temp gigs. The thing I have been chasing – meaningful work that provided a steady paycheck and health insurance in an industry I thought was stable – has turned out not to be so reliable after all.

“What are you going to do now?” a customer asks Kathleen as she rings up books (and stuffs in a box of Kleenex) at the closing sale. She gives a vague but honest answer: she’s going to take some time. We see her doing just that in the last third of the movie: reading a thick novel at a coffee shop, buying plants and produce with Joe Fox, heating up a bowl of soup and sitting on the floor in her apartment to eat it and bask in the sunshine. I suspect she also must have done some grieving. She must have wondered – what now? Earlier in the film, she had wondered in an email if her life’s smallness meant it didn’t have value, or that she lacked courage. Now, that life is no longer available to her, and she has to figure out the next step on a road she never saw coming.

We don’t get a tidy resolution of Kathleen’s career story; we don’t get to see her take her next professional step, though she hints that she’s working on a children’s book. I hope that whatever she does next, it is rich and satisfying and allows her to use all that experience from decades of working at the store. I hope her previous life leads, in both good and surprising ways, to her next one. I hope she realizes how brave she truly is – as Birdie tells her, “You are daring to imagine that you could have a different life.” I hope she’s happy with Joe, of course, but more than that I hope she is fulfilled in her own skin and satisfied with the way she gets to spend her days.

My hopes for Kathleen, of course, are also my hopes for myself. (Isn’t that what we do with our heroines – see ourselves in them, and then project our own hopes onto them?) In the wake of an extremely difficult year, I am hoping – and searching – for a steady paycheck, for sure. But I am also hoping for work that gives me a rich, satisfying, joyful way to spend my days. I think Kathleen would approve.

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