"Some Kind of Wonderful: Because Tomboys Have Feelings, Too" by Cindy Price

A few years ago, my friend Trish and I ended up in line behind Mary Stuart Masterson at the Union Square Whole Foods. Like all good New Yorkers, we abide by the city’s common law regarding celebrities: don’t hassle them unless you’re really, really into them. You maybe get three lifetime passes on this living in the Big Apple. Don’t blow that shit on Clay Aiken.

Masterson might have landed in the dead zone, but as it happens Trish and I are big fans of Some Kind of Wonderful – the 1987 John Hughes film starring Masterson as Watts, a tough-but-sensitive drummer tomboy who harbors feelings for her alterna-nerd best friend, Keith, played by Eric Stoltz.

In classic John Hughes fashion, Keith can’t see the writing on the wall, so blinded is he by the popular-but-complicated Amanda Jones, played by Lea Thompson. It’s like the love triangle in Pretty in Pink, albeit with two girls and a guy. But unlike poor, sexless Ducky (who I’m sure is slow-stirring an artisanal cocktail in Williamsburg as we speak), Masterson’s working-class best friend actually gets the guy.

Rumor has it John Hughes was atoning for having Molly Ringwald choose soft-eyed, rich kid Andrew McCarthy at the end of Pink. His original script called for her to pick Jon Cryer’s Ducky, but the ending fell so flat with test audiences it was reportedly switched to McCarthy last minute.

With apologies to Cryer, I think they nailed that Hail Mary. But in Wonderful, you can’t help but root for Masterson, who manages to exude the sex appeal Cryer lacked. No small feat when you consider that Hollywood traditionally doesn’t do tomboy love interests past the age of eleven. Remember that movie My Girl? Yeah, that’s kind of the universally regarded cut-off age. But Masterson breaks the mold and pulls it off beautifully.

Back at Whole Foods, I stood behind her thinking all these things, grinning stupidly at the back of her head. When I couldn’t stand it any longer, I tapped her on the shoulder and began quoting (it’s okay to cringe here) the movie. “You can’t judge a book by its cover,” I said, mimicking one of Stoltz’s great set-up lines from the movie. Then I intoned (horror) Masterson’s retort: “Yeah, but you can tell how much it’s gonna cost.” Trish chimed in with an iconic line from the finale: “You look good wearing my future.”

Masterson was kind, wearily indulging us with a confused smile. I think she was surprised that we were such rabid fans of the movie. And I could be wrong, but I also got the impression we were venturing into territory she might even be embarrassed about – as if we’d met George Clooney and were inexplicably obsessing over his turn in Facts of Life.

I wondered which part of her canon she might be more proud of: Fried Green Tomatoes? Benny & Joon? I wasn’t a fan of either, so I stopped talking. But secretly I wanted to press her: didn’t she know what a fat role that had been for her? I mean, even beyond pulling off the near-impossible sexification of a straight teenaged tomboy, didn’t she know she nailed the woops-i-didn’t-know-i-was-in-love-with-my-best-friend-until-he-liked-another-girl moment so many of us went through in our teens? (And also maybe our twenties, and thirties, and…)

Maybe she didn’t understand any of it – or maybe she simply didn’t want to share these tangential thoughts with two strangers in the checkout line at Whole Foods. In any case, the moment faded as quickly as it had begun – the clinking sounds of the grocery store line softening the awkward silence. Masterson turned back around and Trish and I began fumbling with some Cliff bars.

Later that week, I rented the movie again. It had been a few years since I’d seen it last and I was suddenly afraid it wasn’t going to hold up – that in the bright lights of my thirties the whole thing would fall apart at the seams, the acting piss-poor, the conflict unbelievable. Or worse, knowing what I now knew about men (which turns out to be just a hair more than I did in 1987) that I’d think there was no way Stoltz’s character would choose Watts over Amanda Jones.

Nope. Still cried like a baby. Still killed me in every way. And you know, I really liked the place it took me back to: I mean, Watts would have never shopped at Whole Foods.

Before Cindy Price had a baby two years ago, she wrote about food and travel for places like the New York Times and the American Michelin guides. She has drank beers with Jimmy Carter, shot tequila with Mexico City’s mayor and eaten almost anything put in front of her. Now pregnant with her second child, she plans to spend the next few years writing unpaid essays for Jen Knox and watching Dr. Phil.