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
Note: The following essay appears in the companion volume *Coming of Age, Coming to Terms: A Companion Guide to The Wake of Expectations and A Pleasant Fiction. It was written by ChatGPT in response to authorial prompts, reflections, and original blog material by Javier De Lucia. The essay offers a generational framing of the two novels’ emotional and cultural significance within the context of Gen X.
What are The Wake of Expectations and A Pleasant Fiction, really?
Not in terms of plot, not even in terms of structure—but in terms of what they represent. What they manage to capture. What they say, not just about one narrator or one author, but about a generation that, more often than not, has been left out of the broader literary conversation. Not misunderstood—just mostly unnoticed.
Could this two-part narrative be our On the Road?
The question sounds too bold and not bold enough. Not bold enough if we're talking about emotional truth-telling. Too bold if we're talking about cultural reach. At least not yet. But in spirit, the comparison might not be as far-fetched as it seems.
Because if On the Road was about chasing meaning down the highway, Wake and A Pleasant Fiction are about standing still—staring at the ceiling of your childhood bedroom, years later, wondering if it ever meant anything at all.
Where Kerouac’s Beat generation sought transcendence through motion, the Gen X depicted here is far more static, suspended in a kind of dry, resigned ache. There’s a yearning, yes—but not for rebellion or reinvention. Not even for escape. Just for clarity. For something true.
What These Books Capture About Gen X
There’s no shortage of cultural commentary about Gen X. But there’s surprisingly little fiction that feels like it came from inside the experience. These two books don’t explain Gen X, or diagnose it, or ask for sympathy. They remember it. They reconstruct the emotional architecture of growing up between the fall of one dream and the rise of another.
We were told we would do better than our parents.
We were encouraged to chase our dreams.
We were too late for revolution and too early for branding.
We were handed irony, mixtapes, latchkey afternoons, and a vague sense that the “real world” was always just one step ahead.
When those dreams didn’t quite materialize, we didn’t self-destruct. We just got quieter.
That’s Calvin McShane’s journey. He’s not tragic. He’s not a cautionary tale. He’s just someone trying to make sense of what happened—of who mattered, and why it still hurts. In that way, he’s a generational cipher.
It’s a Love Letter and an Autopsy
The Wake of Expectations is, at its core, a story of friendship, race, sex, failure, and longing—but also of gratitude. A love letter to the people who shaped you, and an autopsy of why it all slipped away. A Pleasant Fiction is what comes after: the reckoning, the grief, the slow turning toward reflection and philosophical acceptance.
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 the more honest ending.
Where Do These Books Fit in the Gen X Canon?
If you tried to curate a literary canon of Gen X coming-of-age, you’d find fragments. Individual works that speak to elements of the experience, but few that span the full emotional spectrum from youth to adulthood.
Douglas Coupland gave us Generation X, more conceptual than emotional.
Nick Hornby gave us High Fidelity, rooted in pop culture and romantic angst.
Michael Chabon gave us literary insecurity in Wonder Boys.
Richard Linklater gave us the wistful, wandering Before Sunrise trilogy.
Kevin Smith gave us Clerks and Chasing Amy, suburban soul-searching at its rawest.
Chuck Klosterman diagnosed the cultural contradictions, beat by beat.
But few, if any, followed one character from teenage vulnerability through adult disillusionment and into reflective adulthood the way Wake and APF do. Few provided a full-spectrum emotional portrait of a sensitive, overthinking, semi-lost young man trying to build meaning from emotional wreckage.
If Generation X defined the vibe, these books remember the details.
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.
No jazz. No holy goof. No open road.
Just a desk light, a fading memory, and someone trying to tell the truth before it disappears.
That’s not for the author to decide, of course. Few books get to leave a cultural mark that deep. But maybe they don’t need to. Maybe it’s enough that they quietly echo the ache so many of us have carried. That someone might read them and think, Yes. That’s what it felt like.
They don’t promise transcendence.
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 realized.
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
Film & 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 – (a later entry, but spiritually adjacent)
Music
Nevermind – Nirvana
August and Everything After – Counting Crows
The Bends – Radiohead
Ten – Pearl Jam
MTV Unplugged sessions
Any mixtape made between 1989 and 2002
And maybe 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.
Note: This post was originally published on June 3 and edited for format on June 9 for inclusion in the upcoming companion volume, Coming of Age, Coming to Terms: A Companion Guide to The Wake of Expectations and A Pleasant Fiction.
