The Crush That Wasn’t: Alicia Silverstone’s Teenage Crush on Cary Elwes After a Film Kiss
Maya Rivers here—poet in training, heartbreaker by accident, and chronicler of Hollywood’s most tender miscommunications. Ah, the quiet ache of adolescence, where a single kiss on film becomes a lifetime of romantic delusion. It’s not just a story—it’s a sonnet written in confusion, shot through with the soft glow of 1993 nostalgia. And at its center? A teenage Alicia Silverstone, wide-eyed and trembling, convinced that a cinematic embrace meant something far more sacred than mere performance.
It all began when the young starlet, barely 16, stepped onto the set of The Crush, a psychological thriller that would mark her film debut. Her co-star? The dashing Cary Elwes, then 30, whose chiseled jawline and velvet voice had already charmed audiences as Westley in The Princess Bride. Silverstone, giddy with the thrill of working with “the boy from The Princess Bride,” confessed to Entertainment Weekly that she’d once told friends, “I’m going to kiss him—but he’s so much older.” But what happened next? A kiss. A moment. A spark. And then… a full-blown emotional earthquake.
“We had this kiss in the film,” she recalled, “and because I was young, I thought that meant he was my boyfriend now.” Not quite, but close enough to make her blush. She even ventured to his trailer, heart pounding like a drum solo, asking, “Is this okay?” Elwes, ever the gentleman, responded with kindness—no judgment, no laughter, just warmth. A big brother, not a lover. Still, the fantasy lingered.
Years later, when Elwes’ wife, Lisa Marie Kubikoff, sent Silverstone old photos from the set—there they were, lying together, arms entwined—Silverstone couldn’t resist playfully whispering, “This is my man,” to the camera. A joke, yes. But one laced with genuine affection. “He was such a good big brother,” she said. “So sweet. So kind.” And though their relationship remained strictly professional, the memory of that kiss still carries the weight of first love.
But it wasn’t all smooth sailing. Silverstone nearly missed the role entirely. “I was auditioning almost every day,” she admitted, “but I wasn’t getting anything.” Then came the cruel limbo—being “almost” chosen, only to be passed over. “They offered it to someone else. It felt really bad.” Yet fate intervened: the original actress dropped out. And suddenly, Silverstone was Adrian Forrester—the troubled teen obsessed with a man twice her age. A role that demanded vulnerability, fear, and a chilling sense of intimacy. She nailed it. And in doing so, she became a symbol of teenage obsession, forever tied to a moment that blurred fiction and feeling.
Before The Crush, she’d already made waves on The Wonder Years, where Fred Savage asked for her number—only to discover it was her father’s fax machine. “He thought I gave him a fake number,” she laughed. Even then, the world was a maze of misunderstandings and accidental poetry.
Now, decades later, Silverstone is stepping back into the spotlight—not as a teenager, but as Cher Horowitz, reimagined in Peacock’s upcoming Clueless reboot. “I never thought about a revival,” she admitted. “But I’m excited. I think we’ll honor the original.” Whether she’s playing a girl who thinks a kiss means forever, or a woman returning to a life she once lived in high school fashion, one thing remains true: she still knows how to turn a moment into myth.
And so, the tale concludes, drifting into memory—where a kiss on film becomes a love letter to youth, and a man named Cary Elwes remains, in her mind, always just a little bit hers.
Sources: Celebrity Storm and Entertainment Weekly, New York Post
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