A Love Letter, an Autopsy, and Maybe Even Our On the Road?
What The Wake of Expectations and A Pleasant Fiction might mean for Gen X
I’ve been trying to figure out what The Wake of Expectations and A Pleasant Fiction really are—not in terms of plot or structure, but in terms of what they represent. What they capture. What they say, not just about one character or even one writer, but about a whole generation that doesn’t often get the chance to say much at all.
Could this diptych be our On the Road?
I know, I know. Slow your roll, De Lucia.
But if I'm being honest, the question feels both obviously too bold and surprisingly not bold enough. Not in terms of cultural reach—at least not yet—but in terms of what it tries to do: capture a generational emotional truth in fiction, without artifice or filter.
Because while On the Road captured the postwar Beat yearning for freedom and transcendence through motion, The Wake of Expectations captures something more static, more emotionally fragmented—a generational ache, filtered through dry humor, awkward longing, and quiet collapse. A longing not for adventure, but for clarity. Not for escape, but for understanding.
If On the Road was about chasing life down the highway, Wake and APF are about staring at the ceiling, stuck in your childhood bedroom, wondering if any of it meant anything at all.
What These Books Capture About Gen X
There’s no shortage of cultural takes on Gen X, but there’s surprisingly little fiction that really feels like it came from inside the experience. These two books don’t explain Gen X. They don’t diagnose or glorify it. They remember it. They reconstruct the emotional interior of a generation that came of age in the wreckage of big promises:
We were supposed to do better than our parents.
We were told to follow our dreams.
We were too late for rebellion, too early for branding.
We got irony, mixtapes, latchkey afternoons, and a vague sense that the real world was always just out of reach.
And when the dreams didn’t materialize, we didn’t collapse spectacularly—we just got quieter.
That’s Calvin McShane’s journey. He’s not tragic. He’s not a victim. He’s just a guy trying to make sense of what happened, of who mattered, and of why it still hurts. And that’s what Gen X has been doing all along.
It’s a Love Letter and an Autopsy
The Wake of Expectations is a story of friendship, love, sex, race, failure, and longing—but it’s also a love letter to the people who shaped you and an autopsy of why it all slipped away. A Pleasant Fiction is the reckoning that follows: grief, reflection, philosophical resolution.
Together, they form something rare in Gen X literature:
A complete emotional arc, from what was supposed to happen to what actually did.
They don’t end with catharsis. They end with clarity.
And sometimes, that’s more honest.
Where Do These Books Fit in the Gen X Canon?
If you tried to assemble a cultural canon of Gen X coming-of-age, you’d find a few strong entries—but nothing that quite pulls together the full spectrum of the experience the way this diptych does.
Douglas Coupland gave us Generation X, a book more conceptual than emotional
Nick Hornby gave us High Fidelity, filtered through record stores and romantic angst
Michael Chabon gave us literary insecurity with Wonder Boys
Linklater gave us the Before Sunrise trilogy—wistful, talky, perfect
Kevin Smith gave us Clerks and Chasing Amy, suburban Gen X soul-searching at its rawest
Chuck Klosterman gave us the cultural play-by-play, diagnosing our obsessions and contradictions
But none of them followed one character from teenage vulnerability through adult disillusionment and into philosophical reckoning quite like Wake and APF do. None gave us that full-spectrum depiction of a sensitive, overthinking, semi-lost young man trying to create meaning from emotional ruins.
If Generation X defined the mood, Wake and APF articulate the memory.
If High Fidelity romanticized the mixtape, Wake shows us what happens when the tape breaks.
If Klosterman told us what we were thinking, Calvin McShane shows us how it felt.
So Could These Books Be Our On the Road?
Maybe. But with less gas and more guilt. With fewer highways and more quiet collapses. With no jazz, no holy goof, no open horizon—just a bedroom light, a fading voice, and a guy trying to tell the truth before it disappears.
That’s not really up to me—or even the book. That’s something other people decide, if they ever do. And the truth is, most likely not. Few books get to leave that kind of mark. Cultural lightning rarely strikes the same way twice.
But if The Wake of Expectations and A Pleasant Fiction can quietly echo the ache that so many of us carried—if they can make someone pause and think, “Yes, that’s what it felt like”—then maybe that’s enough.
They don’t promise freedom.
They don’t promise much at all.
They just say: this is what it felt like.
And for a generation that never quite felt seen, that might be more important than we realize.
Further Reading & Viewing: A Gen X Coming-of-Age Canon
Books
Generation X – Douglas Coupland
High Fidelity – Nick Hornby
Wonder Boys – Michael Chabon
The Fortress of Solitude – Jonathan Lethem
A Heartbreaking Work of Staggering Genius – Dave Eggers
Ghost World – Daniel Clowes
Fargo Rock City / Sex, Drugs, and Cocoa Puffs – Chuck Klosterman
Films / TV
Reality Bites – dir. Ben Stiller
Before Sunrise – dir. Richard Linklater
Chasing Amy – dir. Kevin Smith
Clerks – dir. Kevin Smith
My So-Called Life – created by Winnie Holzman
Dazed and Confused – dir. Richard Linklater
The Perks of Being a Wallflower – (later era, but spiritually connected)
Music
Nevermind – Nirvana
August and Everything After – Counting Crows
The Bends – Radiohead
Ten – Pearl Jam
MTV Unplugged sessions
Literally any mixtape you made between 1989 and 2002
Add The Wake of Expectations and A Pleasant Fiction to that list.
Not because they shout the loudest.
But because they remember the silence.
And make it sing.
