The Hughes Ending That Never Comes

Aug 20

A Reflection on Pretty in Pink, Some Kind of Wonderful, and The Wake of Expectations

I previously wrote about Ferris Bueller’s Day Off and how the humor in that film reflects the tone of The Wake of Expectations. This month marks the 40th anniversary of my favorite John Hughes film: Weird Science.

In honor of the occasion, I’m doing another Hughes-themed post—though, ironically, not about Weird Science. Because while there’s some Jake-Cal energy in the Gary-Wyatt friendship, the deeper character parallels to The Wake of Expectations come from a different corner of the Hughes catalog.

⚠️ Spoilers for The Wake of Expectations plus light spoilers for Pretty in Pink and Some Kind of Wonderful.

If you grew up on John Hughes films, you already know the emotional blueprint:
The best friend who pines in silence. The “nice guy” who doesn’t get the girl. The misunderstood misfit. The unattainable crush. The kiss that changes everything—or doesn’t.

So when readers meet Calvin McShane, it’s tempting to look for familiar touchpoints.
Is he a modern-day Ducky? A male version of Watts?
Is Dani his Andie? His Amanda?

The answer is more complicated.

🎭 Calvin vs. Ducky: The Nice Guy, Rewritten

Ducky Dale (Pretty in Pink) is the original friend-zoned martyr—flamboyant, performative, and loyal to a fault. His longing is loud, theatrical, and sometimes borders on entitlement. He’s less a character than a trope: the Nice Guy who believes that friendship, when deep enough, should naturally lead to romance.

Calvin may share some surface traits—emotional sincerity, a deep connection with someone who doesn’t return his feelings—but the internal story is very different.

Ducky expects to be chosen.
Calvin believes he already has been…maybe.

The signs were there. The late nights. The emotional intimacy. The occasional kisses. The kind of closeness that doesn’t feel casual. The connection feels real, mutual, and in motion. Calvin doesn’t press. He lets it unfold.

Until the moment he reaches for more.

And everything stops.

She pulls away. He pulls back.
And in that frozen instant, he knows he’s done something wrong—he just doesn’t understand why.

Not because he’s entitled. But because the world he thought he was in suddenly collapses.

Ducky’s heartbreak is performative—sharp-edged and noisy, full of accusation and flair.
Calvin’s heartbreak is silent. Embarrassed. Shaken.
Not “How could you not want me?” but “How did I get this so wrong?”

🥁 Calvin vs. Watts: Unspoken Longing and Ungrasped Endings

Watts (Some Kind of Wonderful) is the patron saint of the silently heartbroken best friend. She’s loyal, wounded, sarcastic, brave—and terrified. She kisses Keith under the pretense of “practice,” but that moment is anything but casual. It’s confession disguised as convenience. Vulnerability hidden in plain sight.

And in the end? She’s rewarded. Keith sees her, finally. The emotional arc resolves.

Calvin shares her vulnerability. His longing is quiet, tangled in fear. But unlike Watts, his moment is not transformative. There’s no last-minute realization. No romantic reversal.

If Ducky is entitled and Watts is victorious, Calvin is resigned.

He doesn’t lose a girl—he loses a possible future. A version of life that slips away, undefined and unclaimed.

💔 Dani: Not Amanda, Not Andie—Watts Without the Want

And then there’s Dani.

She’s not the aloof dream girl. She’s not emotionally distant. She’s warm, funny, present, intuitive. The bond she and Calvin share is deep and unmistakable. There’s affection, trust, a kind of intimacy that feels like the beginning of something—at least to him.

Because for Calvin, they’re moving. Moving toward something more.
Moments of closeness build. Kisses come—then don’t—then return.
They go out together. Sometimes it feels like a date. Sometimes it doesn’t.
The line between friendship and something else feels like it’s just waiting to be crossed.

But what Calvin doesn’t know—what he can’t know—is that Dani isn’t on the same path.

She’s not resisting him.
She’s protecting herself.

Dani has experienced things she’s never spoken about. Her relationship to desire, to trust, to physical closeness—it's complicated in ways even she hasn’t fully processed. So when Calvin finally leans in—emotionally and physically—hoping for clarity, for progress, for something honest and unambiguous, she shuts down.

To him, it feels like rejection. Sharp. Sudden. Humiliating.
But for Dani, it’s something else entirely.

It’s survival.

She doesn’t reject him—not consciously. She just can’t go where he wants to go.
Not then. Maybe not ever.
And after that moment, never with him.

And because she doesn’t explain the “why”—because she doesn’t have the words for it herself yet—Calvin is left to interpret the moment through the only lens he has: the confusion, the buildup, the hope… and now, the silence.

Something inside him breaks.
And what had once felt like a connection becomes a wound.