The Best Time I Realized Sleepless in Seattle Sort of Sucks

by Amy Lynch

In 1993, I was a bodysuit-wearing, barely-been-kissed, e.e.-cummings-quoting, show-tune-singing, sentence-diagramming 17-year-old, and the Nora Ephron way just resonated. Reeled in by a delicious Cole Porter-tinged soundtrack (so adult!) with a dash of Harry Connick, Jr. (my then-future husband, I was sure of it), I was a Sleepless in Seattle devotee before the opening credits faded in the dank movie theater at the mall where I breathlessly watched Meg and Tom pretend to fall in love for the first of however many times.

Nora Ephron was roundly revered as the most successful female screenwriter and director of that time, and I made her my imaginary mentor. I couldn’t quite identify with her characters’ privilege and pomp, but when references flew over my head or the ethnic sameness of all the characters started to seem irksome, I chalked it up to the fact that I was a lower-middle-class kid from Florida, untouched by all things cosmopolitan and therefore unable to appreciate New Yorkers’ high-falutin’ neuroticism and penchant for homogenous cliques. I loved schmaltz and smart dialogue and wanted so badly to be a writer, and that made me an inevitable devotee, a junior member of Nora’s clan.

This year, on New Year’s Day, I turned to my boyfriend, a gentle giant who loves Shakespeare, Metallica and Doctor Who in equal and uncomplicated measure, and suggested we watch one of the very playbooks I probably used in some way to make him fall in love with me three years ago. Open-minded soul that he is, he agreed, and the movie that had once been my favorite romance unveiled itself anew as a slightly insulting horror show.


Sleepless starts off sweetly enough, right? Man loses wife, man and son move to Seattle, son calls Delilah-After-Dark-esque radio show to ask how Dad can ever be happy again, women the nation over swoon against the FM radios in their cars. Aw. Horses, horses, horses, horses, y’all. But then! Annie shows up across the street from the shoreline where Sam is playing with his eight-year-old son, Jonah, in the sand. She’s flown to Seattle from New York to meet him, unannounced and anonymous, as you do.

My boyfriend laughed. “This is one gender reversal away from Law & Order: SVU,” he said. “Is there a horror version of this on YouTube?” (There is.)

Oh god, I thought. I’ve been brainwashed.

To recap, Annie is contemplating… leaving? cheating on? her fiancé, Walter (the always affable Bill Pullman), whose most egregious offense is having lots of allergies. She hires a private detective to photograph a widower she’s never met and flies across the country on the company dime to physically hunt him down. Then, with a nudge from her dysfunctional, funny BFF (Rosie O’Donnell), she arranges an Affair To Remember-inspired meet-up at the top of the Empire State Building — a plan whose execution requires the breaking off of her engagement over a Valentine’s Day dinner with poor old Walter and a dash up the avenue to hop on an elevator before the building closes.

In the movie it’s not cruel, psychotic and ridiculous; it’s cute! Nevertheless, there are signs. When the wedding dress rips. When she can only say hello. When she looks out a top-floor window in midtown Manhattan and can see the Empire State. What are the odds on that last one, I ask you?


In the kid’s defense, he hasn’t — “YOU WOULDN’T LET ME,” he screams. In my defense, I was 17, and I hadn’t either. And in Nora’s defense, nobody could spin a meet-cute like she could. So even if little Jonah had been scared shitless already at the Glenn Close prototype, so expertly laid out for all of us to avoid (not just men, but anyone who doesn’t want to die at the hands of a stalker), he still might have thought Annie was a keeper.

Such is the danger of the romantic comedy.

In the end, we all know the two walk off together, hand in hand, a satisfied Jonah in tow. They step onto the elevator of the Empire State building and begin their life together, we assume, and on Valentine’s Day, naturally. I have to wonder how that elevator conversation actually went, though: “Hey, haven’t I seen you across the street from my house, spying on my young child?”

This movie, and a lot of other movies in this genre, spend a lot of time talking about fate, destiny, kismet — and signs. Are we the captains of our own ships? they all ask, and in most cases, the assumed answer is contradictory: “No, of course not. But still, go get your man.” In Sleepless, although the storytelling is remarkably intelligent, something central remains awry. Here, it’s the self-determined woman’s turn to pursue what she wants, but the only way to make it entertaining — plausible to an audience, even — is to make her cute and plucky (always plucky, no exceptions) to the point of being batshit insane. And she’s not really self-determined, though she thinks she’s calling the shots, though she insists that she “doesn’t believe in signs.” The heroine of a rom-com almost never really gets to decide anything. There’s always that cherub out there with an arrow, pointing it straight at her chest.


It’s often in the midst of a Netflix binge that we come to see ourselves most clearly. But the signs that I was losing my once-total devotion to Nora had been there for years.

Last fall, I exchanged emails with her sister and frequent co-writer and producer, Delia, for a magazine assignment. In preparation, I devoured Delia’s memoir (out last year) in two sittings and realized that she — the careful, empathetic little sister to bold, brash, brazen Nora — was more my kind of lady than her sibling (if your heart beats, Delia’s essay “Why I Can’t Write About My Mother” will break it). Realizing this, I took selfish liberties in drafting my questions for her, and I wasn’t disappointed with her answers.

“Don’t marry a man just because he asks you,” she offered, when I asked what advice she would give her twentysomething self, given the chance. “Not that getting that obvious advice would have stopped me.” Having described her twenties as “one big walkabout” and admitting to not finding her voice as a writer until her thirties, she spoke in a language to which I could relate — the language of a woman who’d emerged from some spectacular disasters in her professional and personal life and gotten some snappy copy out of it.

Not long afterward, I picked up a copy of The Most, the final collection of works Nora compiled before her death. On nearly every page, there’s compelling evidence that her role as a strong, smart trailblazer in the realms of journalism, film and feminism was painstakingly earned. I had aspired to her example, and still do.

But really, I lost my membership card to the Annie and Sam fan club a long time ago, around the time I began losing patience for guys who looked skyward for direction. In the middle of the two biggest breakups I went through before finding my way into a bigger league, the long-armed, gun-shy mama’s boys I’d entrusted my heart to each said something along the lines of, “I just wish some kind of sign would show up and tell me what to do.”

My first thought, both times, was “What are you, a girl in a romantic comedy?”

I attempted to go to the top of the Empire State Building once — on Valentine’s Day, of course — with the first of those two sign-seekers. It was 2003 or 4, I think, while we were visiting friends. The line for the observation deck spilled out of the building and wrapped around the block. The wait to get to the top was something like three hours.

I looked up into his face to see if he was willing to wait that long. He scrunched his nose, so we wandered down the street for sandwiches instead. As we finished our food, I surprised him with a compass I’d seen him eyeing the week before at some store in the mall; I’d bought it when he wasn’t looking.

We broke up pretty amicably — and for good reasons, too — a few years later, and never spoke again. I’ve since moved to Austin, where my first encounter with my new city was an Ephronian meet-cute in and of itself. No one would ever describe me as “plucky.” I still find myself diagramming sentences sometimes, though, and the Great American Songbook still seasons my playlists. I know it always will.

Oh, but as for signs: back at that bar in New York, before I handed the compass over, I have to say I’m curious if it said I was facing west. Yes or no, I’m still pretty sure I’d have ended up heading that way.

Amy Lynch is a freelance writer and editor based in Austin, Texas. Follow her on twitter at @onesmartpoptart.