One Chance: Understanding Queerness in Sleepless in Seattle

One Chance: Understanding Queerness in Sleepless in Seattle

So many queer teenage crushes are experienced from afar, which somehow brings Tom Hanks and Meg Ryan’s long distance romance a little closer. A lot of ‘90s rom coms might exclude the queer experience – but Nora Ephron’s romance somehow understands it perfectly, according to Tina Kakadelis.

The year I was born, Nora Ephron released Sleepless in Seattle, a film which partly takes place in the city where I grew up. The first time I saw the movie, I was home sick from school. In a hazy daze, I saw Jonah make the fateful phone call, Sam’s forays into dating, and Annie’s cross-country journey to Seattle on a pure whim.

Sleepless in Seattle is built on longing and foolish hope. It’s the perfect way to describe teenage love and, more specifically, being a closeted lesbian in the early aughts. My teenage crush did not span the 2,763 miles from Baltimore to Seattle. It spanned mere inches across the shared desk in a high school Honors World History class. But to me, those inches might as well have been the distance to the moon. 

Fifteen-year-old me knew she was the prettiest girl I’d ever seen. Back then, though, I don’t think I recognized that feeling for what it was. Not at first. I made all kinds of excuses to explain why I kept getting in trouble for making her laugh. You can rationalize anything away so that you don’t have to face the reality of why you’re feeling this way or acting like this, but the truth is always there. Lingering in the back of your mind, gnawing at the cage you carefully constructed. That first real crush is sticky sweet like honey. More than a decade later and I still remember the way my heart would race in anticipation of seeing her.

I’ve written about the girl from my Honors World History class so many times that I’m sure she knows now. I’m sure she’s aware of all the feelings I was too terrified to put into words when I was 15 and awkward because I’ve spent so long trying to right my wrongs. Painfully going over every missed opportunity. That’s the problem with opportunities, they’re like Schrodinger’s Possibility. Until the opportunity is finally punctuated with a period, the happy ending is still a potential outcome. Sure, you can recognize that these hopes are irrational, but that doesn’t stop you from wondering, “what if?” It’s what sustains Annie throughout the entirety of Sleepless in Seattle. Yes, it is absurd to throw your life away for a stranger all the way across the country…but what if this man on the radio is The One? Yes, I’ve long since moved away from being the shy kid in World History class…but what if that girl called me up right now?

When I was younger, I was desperate to go back in time. To take all the confidence and self-assuredness I’ve gained with age and bestow that gift on my 15-year-old self. To give my feelings the freedom to exist loudly, a luxury I didn’t realize I was missing. To offer myself a chance to give this story about a girl an ending. When you’re afraid that people will figure out you’re queer, any semblence of emotion is too big. Feelings go into a miniscule box that’s tucked so deeply within the depths of your soul it’s like it doesn’t exist. I thought I was doomed to only experience love quietly on my own and to keep hope alive through stolen, one-sided moments like Annie. I lived for the passed notes with the swirly, almost-cursive writing the same way Annie dropped everything to tune into Sam’s voice on the radio. I saw these insular, restrained acts as the pinnacle of romance. Of course, that isn’t love at all.

When you’re young, you want to be loud. You can promise to meet someone on top of the Empire State Building because you’ve never known how lonely that elevator ride to the top can be. That’s why Annie is so brave when she takes that last elevator ride to the top. Yes, there’s the issue of her leading Walter on for much longer than she needed to, but I always cut her some slack because I felt like I understood. Walter was fine, and most days Annie could trick herself into thinking that fine was enough to build a life on. It’s the same way I convinced myself there was a boy out there somewhere I could like. A boy with nice enough eyes and an interesting enough personality to be fine.

And then the possibility comes along for something too magical to ignore. It’s Sam’s voice on the radio, or a smile from a pretty girl on college move-in day. It’s so overwhelming and all-consuming that you do take that ride up the elevator, despite knowing the odds. Despite knowing the multitude of ways it could go wrong, you kiss that girl for the first time in your dorm room. Part of the magic of Sleepless in Seattle is that there’s no look at Sam and Annie’s life after they meet. The audience never sees them in the real world, there’s no decision about whether to move to Baltimore or Seattle. For all we know, they never make it past the elevator ride back down. That isn’t what’s important here. What matters is what happens on the Empire State Building on Valentine’s Day. It’s showing up for a chance at something that is not guaranteed, for a shot at desire.

For a lot of my life, I romanticized the longing. The way Annie would get so emotional as she listened to Sam’s voice on the radio, how she could quote An Affair to Remember effortlessly, and prehistorically cyberstalk him with her newspaper connections. I emulated that by nurturing crushes for far too long without doing anything. I don’t know how many possibilities I missed because I didn’t say anything. That’s thanks in part to the lack of romantic comedies with queer leads that existed in the early 2000s. Instead of romantic rendezvous on the tops of buildings, it was homophobic jokes and queer women who were destined to die before they could even glimpse a happy ending.

There’s a time and a place for the yearning so elegantly captured in Sleepless in Seattle. There will always be something tantalizing about the wanting. The build-up to the moment when it’s finally put out in the open, but we cannot live in the climb. The scales must tip one way or the other. The highs and lows of romance are not found by keeping things in equilibrium.

Sleepless in Seattle quickly became my sick day movie. It’s the sort of soothing comfort film that Ephron perfected throughout her career, but revisiting it now, I understand Annie in a different way. Before, I clung to her unsubstantiated devotion to a faceless man because that was all I knew for myself. Now, I’ve had a taste of a love that’s big and beautiful and bright enough to inspire me to fly across the country. Just for a chance.

Tina Kakadelis (she/her) is a freelance critic and pop culture writer based in Pittsburgh and the unofficial president of the under 30 Bruce Springsteen fan club. You can find her on Twitter and Letterboxd @captainameripug or browse all her writing on

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