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The Place You're Supposed to Laugh

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It’s 2002 in Silicon Valley. 9/11’s still fresh, the dot-com bubble has burst, and holy calamity is raining down on 14-year-old Chad Loudermilk. His father is about to lose his job, his mother isn’t the same since Chad’s grandma died, and as one of the few black kids at tony Palo Alto High School, Chad’s starting to wonder about his birth parents. Next door lives dot-com mogul Scot MacAvoy, with his luxury SUV and his gardeners and his beautiful wife and his time to play video games with Chad, all making the Loudermilk family’s struggle to stay afloat seem that much harder. It’s going to be a tough year for the Loudermilks.

THE PLACE YOU’RE SUPPOSED TO LAUGH is wise and witty novel about the Silicon Valley that’s not covered in the fawning features in The New York Times. It’s a place where the working class, blended Loudermilk family grapple with issues of race and inequality, all while trying to keep a smile on their faces. In the spirit of the works of Celeste Ng and Angela Flournoy, this is a big-hearted page-turner that will make you laugh, cry, and think all at once.

330 pages, Paperback

First published November 14, 2018

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Jenn Stroud Rossmann

7 books12 followers

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Displaying 1 - 19 of 19 reviews
Profile Image for Lori.
1,806 reviews55.6k followers
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September 13, 2018
This fall I am thrilled to be working with Jenn and this novel, securing reviewers and interviewers. If you like the sounds of her debut novel, and would be in interested in covering it, hit me up for a digital review copy!
Profile Image for Kate Brandes.
Author 5 books97 followers
January 25, 2019
Jenn Rossmann's The Place You're Supposed to Laugh is a big-hearted story told with wit and wisdom.
Profile Image for Ben.
Author 40 books265 followers
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August 4, 2020
It feels impossible to put down, and not because there's suspense or murder or some impossibly transformative idea that must be solved here, now, but because the writing is so fluid and we care so much about our protagonist Chad and because we have to know what happens to him and his family and friends because Rossmann cares so much about them and that leaps off of the page and it's really kind of lovely.
Profile Image for Kate Vane.
Author 6 books98 followers
October 5, 2018
This novel opens with fourteen-year-old Chad on his way to get his father out of jail, in between sleepovers, computer games and wondering who he is. The adults in his life are asking the same question of themselves, with rather less success.

Chad's parents are barely clinging to middle-class status in Palo Alto in the early 2000s, as the winners of the first internet revolution push prices sky high, and the losers decline to quietly slip away.

The struggle to keep up is bearing down on his parents, while his aunt, juggling her academic career and motherhood, is run ragged by success.

The tragicomic bit players in this book are the failed dotcom millionaires. They are a constant reminder that your status is contingent, that the person you thought you were yesterday could be wiped out today, that you too could be doomed to spend your days sitting in a coffee shop with a laptop, shouting at anyone who will listen that you still matter.

I love the way the book is packed with humour and warmth while not shying away from some pretty dark life lessons. Chad is smart, funny and open to experience – and experience keeps coming at him.
*
I received an advance copy of this novel from the publisher via TNBBC Publicity.
Read more of my reviews at https://katevane.com
Profile Image for Hobart.
2,744 reviews90 followers
November 14, 2018
★ ★ ★ ★ 1/2 (rounded up)
This originally appeared at The Irresponsible Reader.
---
Those inclined to irony might find it in the Palo Alto Farmers Market assembled on asphalt, where there had once been an apricot orchard. Each weekend from May through December, the workweek parking lot filled with vendor stands and umbrellas protecting bins of trucked-in garlic cloves, avocados, tomatillos, et al. The University down the street was known as “The Farm,” though it hadn’t been one since the Stanfords donated their country estate and chartered a college in the 1880s. Stanford grads and especially its dropouts had been transforming the Valley ever since; the fruit came from further and further away.


It's really hard to grab a representative quotation from this novel -- but this comes close. There's a hint of the humor, the capturing of a moment in time, societal observation, a hint of wistfulness, and even a modicum of critique.

It's 2002, in many parts of the country the shadow of 9/11 looms large. It's present in Palo Alto, but not to the degree it is other places -- what looms larger is the bursting of the dot-com bubble, everyone around them has been impacted in some way by it -- most people have been impacted in significant ways, although the ripples are still going out from them and affecting the lives of everyone in their community in some way.

Our focus in this novel is on the life of Chad Loudermilk and those who are near him. Chad's 14 and is enduring his first year in high school. His best friend since . . . well, forever, Walter Chen attended there briefly, but was pulled out by his parents to attend the Roman Catholic academy nearby -- for a greater focus on academics, and fewer active shooter drills. Life's hard without Walter around. Chad's mother works with "at risk" youth, on making wise decisions, while she's still reeling from her mother's death a few months earlier. Chad's father, Ray, is dealing with ripples of the burst -- the advertising agency he's part of his dealing with a shift in clientele. There's Scot, Chad's next-door neighbor, the creator of Latte (wink, wink) -- the Macromedia tool -- a big brother figure, dispensing non-parental advice and playing video games (his wife really doesn't have any time for Chad). There's a new girl in school that Chad can't stop talking about, and a couple of guys from the proverbial other side of the tracks that he met at a record store and is spending time with. The major focus of the plot is following Chad's interactions with them over the course of a few months -- we get chapters focusing on his parents and what's going on in their lives, but on the whole, the rest of the characters are seen filtered through Chad's experience.

The other major thread follows Chad's maternal aunt, Diana, a physics professor we meet as she registers for a conference in Barcelona. She's trying to re-establish her career after pressing pause on things to have a child with her best friend. It's not easy for her to get back into the swing of things, but she's close. As Chad's aunt, there's a lot of opportunity for the plotlines to intersect and overlap -- but the sisters aren't that close, so it's not as frequent as it could've been. By the end of the novel, events have transpired enough that Diana's as large a fixture in Chad's life as Scot (maybe larger), so it's easy to intermingle the story lines. But for the first 1/2-2/3 or so, there a clear distinction between the two -- and it's not clear why we're getting both stories.

Another thing that's not clear is what exactly is Chad's story. This is close to a Bildungsroman, but we only really see the beginning of Chad's development -- it's like the first Act of Chad's Bildungsroman. Which isn't to say that it's an incomplete story, it's not. It's just about Chad starting adolescence. You don't want to get the details from me, you want to get them from the book, but a lot of stuff happens. Nothing major like a school shooting, a terrorist attack, or anything. Just life, the ebbs and flows of people's lives. I could actually sum up the major events of the novel in 2 sentences. One of them might be long-ish, but just two sentences.

Don't get me wrong -- there's a plot to this book. But really, you don't see it (well, I didn't see it) until toward the end -- maybe even after the end. This is not a bad thing, it just means you have to think about things a lot. My notes are filled with comments along the lines of "I really don't see where this is going" or "I'm not sure what the point of all this is" -- and they're always followed with, "Don't care, great stuff." I really didn't care where Rossmann was going, I was too busy enjoying the ride -- the voice, the characters, the atmosphere, the little bits like the Farmers Market (above), were enough to keep me engaged, entertained and turning the pages.

I'm not going to drill down and talk about the various characters -- or even just one. I could do a post just about Ray, or Scot, or a long one on Chad or Diane -- I think I'd have to do a series on Chad's mom. Instead I'll talk about them as a collective whole -- they're people. There are things to like about them all, there's plenty to dislike about them all (particularly the adults). A lot of what they do seem inconsistent with the characters as Rossmann has presented them, but that just makes them more human. There's not one character in this book that isn't a human -- no one larger than life (Scot kind of is, but he's larger than life in the way that we all know someone who seems to be that way). Any person in this book could easily be the person next to you in the bagel shop, sipping on their caffeinated beverage of choice. They're delightful in that perceived realism, also in the way that Rossmann talks about them. Without approval of anything, you get the feeling that she has affection for every character in the book.

The clergymen who appeared -- however briefly -- in this book were a couple of the least objectionable depictions of clergy I can remember seeing lately. Not hypocritical, they actually seemed to believe in what they were saying, and were actually trying to help those they encountered. It's not often you get to see that anymore, and it should be acknowledged when you see it.

I've been struggling for a few days -- and I'm not sure I'm succeeding at the moment -- to put into words the experience that is The Place You're Supposed to Laugh. I think I was hooked by the end of chapter 1 -- definitely by some point in the third chapter. I liked the book, I liked the characters, I liked the writing. It's a pleasant, thoughtful experience. It's what reading a book should be like -- skillful writing, wonderfully drawn characters and prose you enjoy immersing yourself in.

The novel talks about a lot of things -- one of the biggest themes is forgiveness. I don't think I've ever seen the topic discussed in quite the same way in any format. I won't suggest that Rossmann exhausted the idea, obviously, but she talked about it, depicted it, and had her characters think about it in ways I found refreshing and encouraging.

I'm not sure what else to say -- The Place You're Supposed to Laugh is a great read. It's a strong novel that will make you think, will make you feel, and will leave you satisfied. Rossman writes with sensitivity, wit and skill. What else are you looking for?

Disclaimer: I was provided with a copy of this novel by the author in exchange for my honest opinion, which is seen above.
Profile Image for judy-b. judy-b..
Author 2 books44 followers
January 14, 2019
The sense Jenn Stroud Rossmann recreates of the cultural dishevelment that rocked Silicon Valley and the San Francisco Bay Area in the early ‘00s is as unsettling as the real thing was. Just as I recall, there are moguls living next to middle-class professionals who are in danger of slipping down a rung on the socio-economic ladder; there are familial tension and fallout that result from cultural upheaval + teen angst + and financial hardship; and there is the specter of Tech, capital-T, hovering over it all. Not for me to say how accurate a portrayal of an adopted African American teen being raised by white parents this is, but there are moments that feel like they could lead a reader to insight. We need to have more conversations about our you’re-in-or-you’re-out, have-or-have-not culture; we need to talk about how we deny the importance of race and status and profession yet place certain values on these identities. This book is a way in to those conversations, and for that I appreciate it.
Profile Image for Kimberly.
25 reviews
December 26, 2018
This was pretty good. I liked the characters and the way the author wrote about a black child being raised primarily by a white mother and absentee middle age crisis father.
Profile Image for Jacquelyn Chappel.
38 reviews1 follower
July 31, 2023
This is a tough review for an excellent writer!

I loved the opening chapter of the book which begins with 14-year old Chad having to pick up his dad from jail! His mom is not there, because she's dealing with her own things, so a neighbor is enlisted to drive. The whole scenario is so deliciously awkward while offering insight into each of the characters: a screwed-up dad, chilly upper-class neighbors, an ineffectual, lost son who is having to grow up real fast, and an absent mother during this fraught moment, suggesting a fractured family about to fall apart.
The details are well-observed and realistic.

But the book fell off a cliff for me when the circumstances surrounding the dad's night in jail are never dealt with. The mom never has a fight with the dad about it. The son never seems to question his dad about what happened, or discuss or even think about the events of that night in any way. We, the reader, find out what happened, but it wasn't enough for me. I needed to see the family members respond. Maybe I missed something, but this inciting moment is just dropped.

The simmering rage which sparked the night in the "drunk tank" comes back about 100 pages later, but by then, it was too little too late for me. From there, the book launched into the dad's slow quiet decline and eventually an odyssey to find a lost mother.

At its heart, the book seems to be about an adopted African-American raised by white parents coming to terms with his identity. But the most dramatic events happen with the dad, the most vulnerable (and therefore interesting) character. In response, Chad, the son, spends his time wringing his hands over approval from his friends of various ethnicities.
Profile Image for Julie.
Author 3 books38 followers
March 27, 2019
When we meet 14-year-old Chad Loudermilk, he’s hitched a ride with his beautiful, posh neighbor to pick up his father from jail, and immediately we’re drawn into his story. The only black kid in his Palo Alto high school, Chad is desperately trying to navigate the rocky terrain of adolescence without much guidance: his best friend has just been whisked off to private school after one too many active shooter drills, his mother, a selfless do-gooder founders in her own grief after losing her own mother, and his father can’t keep his feelings of inferiority in check. The colorful cast of characters also include Chad’s next-door neighbor, a dot come whiz with millions in the bank, a beautiful wife, and seemingly endless time to playing video games with Chad; his over-achieving aunt who’s recently been granted tenure at Stanford; and his two new friends Marcus and Andre from East Palo Alto. Several times, I laughed out loud. Often my heart went out to Chad or the other characters as they strived to figure out their place in the bewildering post-9/11 and post- dot-com bubble world of Silicon Valley. I love a novel that can tackle serious issues of identity, race, class, ambition with warmth and wit, and this book has all of the above!
Profile Image for Jayne Martin.
Author 4 books21 followers
April 3, 2020
Set in 2002 in the wealthy enclave of Palo Alto, California, families still struggling with the emotional fallout of 9/11 find their foundations further shaken by the burst of the dot.com bubble that had financed who they believed themselves to be. At its heart, it's about our need to know who we really are beneath the facade we show the world. The notion of what constitutes a "family" is challeneged through Rossmann's deft and eloquent handling of the characters' emotional lives and interactions with each other in a changing world. This book held me page after page with it's authenticity, its fully-formed characters struggling with their flaws, striving to connect amidst shifting fortunes and friendships. "The Place You're Supposed to Laugh" has heart to spare. I loved it. The readers' guide at the end makes it a natural for book clubs.




Profile Image for Arno.
29 reviews
August 18, 2019
This novel was less about events, and more about the thoughts and reactions of people to the happenings around them.

Through reading their feelings as things slip or crash in their lives, I got pulled in, wondering what would come next. That feeling continues even after the books ending; their lives are works in progress and the picture is still in flux... gives the reader things to keep thinking about.
106 reviews
June 4, 2025
This book has many messages, such as the attitude of the rich toward the poor, the difficulties for a child to fully integrate into a neighborhood of a different race, how to cope with a parent who cheats on the other, how to hold together a totally varied and nonfunctional family, etc. Chad, the teenage protagonist, is so believable that his concerns about those around him seem very real and touching. This book made me think, and that's a blessing.
6 reviews
January 26, 2019
I've wondered what Silicon Valley was like in this time period, so I appreciated this book as a bit of historical fiction, one of my favorite genres. The characters were All well drawn and believable as the book progressed, and I especially appreciated the scientist character and the issues she dealt with. Highly recommended.
Profile Image for Emily.
7 reviews1 follower
August 5, 2019
Highly entertaining! Rossmann's debut novel in my opinion is a hit and should be listed as a New York Times Best Seller! The fictional characters feel real. Rossmann engages you in each of the character's tragedies, love, loss and humor throughout this book (I found myself laughing out loud throughout this book).

Profile Image for Beth.
748 reviews8 followers
May 29, 2025
We had a great bookclub discussion. This book drew me in after initially being a slow start. As someone in my book club commented - who knew one neighborhood could have so many dysfunctional residents!

I had the pleasure of meeting Jenn who discussed the novel's path through ideation, to writing, to publishing, which was interesting

Recommend.
Profile Image for Jennifer.
Author 4 books27 followers
April 19, 2019
A smart, engaging, and moving read. I look forward to Rossman's next book!
Profile Image for Cheyenne.
26 reviews3 followers
February 27, 2023
This book is amazingly written and so interesting that I could not put it down. I felt the author (a yt woman) did a great job writing the main character's perspective (a black male teen) BUT the only other two black teen characters in the book felt so stereotypical and lacked the substance she gave the main character.
Displaying 1 - 19 of 19 reviews

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