A juicy, fun yet piercing debut novel, Smile and Look Pretty tells the story of four assistants working in media who band together to take on their toxic office environments in the ultimate comeuppance—pitched as Sweetbitter meets Whisper Network.
Online they’re The Aggressive One, The Bossy One, The Bitchy One, and The Emotional One. In real life, best friends Cate, Lauren, Olivia and Max all have one thing in common—they’re overworked, overtired, and underpaid assistants to some of the most powerful men in the media and entertainment industries. When they secretly start an anonymous blog detailing their experiences, their posts go viral and hundreds of other women come forward with stories of their own. Confronted with the risks of newfound fame and the possibility of their identities being revealed, they have to contend with what happens when you try and change the world.
Gripping, razor-sharp, and scathingly funny, Smile and Look Pretty is a fast-paced millennial rallying cry about the consequences of whistleblowing for an entire generation, and a testament to the strength of female friendship and what can be accomplished when women come together.
What’s it about (in a nutshell):
Smile and Look Pretty by Amanda Pellegrino is thought-provoking, relatable, and realistic story about the current work conditions for young twenty-something professionals trying to get their break in their chosen careers.
What I Enjoyed:
I enjoyed several aspects of the novel, but I loved the sisterhood of the main characters–Olivia, Cate, Lauren, and Max–the best. They aren’t biological sisters, but their bonds can withstand as much as any genuine sister relationship. They hug and fight, agree and disagree, but in the end, they will always be there for one another through thick and thin. I loved the genuineness of the small nuances that create the complete picture. I even love that they keep secrets from one another because… well… don’t we all have those parts of ourselves that we don’t share unless we must?
This story made me think for a long time after I finished it. I contemplated the state of the work world today regarding harassment and toxic relationships with bosses compared to how it was in the 80s and the 2000s. It saddened me that things, even though they have improved somewhat, still are relatively the same as they were in those decades when such movies as 9 to 5 and The Devil Wears Prada sought to illuminate how badly bosses treat assistants. Here we are in 2022, sexual harassment runs rampant, and the toxicity still exists between some employers and their assistants. I think we can learn lessons from this story to make an even more significant dent in improving work conditions for all but primarily disproportionately targeted women.
I loved the fast pace of this third-person narrated story. The pages just sped by from beginning to end, flipping at break-neck speed the closer I got to the conclusion. I wanted the four young women to win… to come forward and say, “Yes, I am calling out my boss for bad, and in most cases illegal, behavior because I know if I don’t do it, those with the power to do such things will sweep it under the rug.” The women’s empowerment just exudes off of the pages, and I couldn’t help but be swept up in their much-needed movement.
The four main characters are incredibly well-developed, with different backgrounds, issues, and personal challenges. I particularly loved Lauren because of the complex challenges that only she faced challenges stemming from race and skin color and problems of growing up without a father. Her character stood out to me because she was usually the dissenting voice among the four, and learning what made her tick taught me so much. I spent a lot of time telling her to take a leap of faith and just do it. Lol. If ever you talk to characters in a story, this one will be it. Cate is the most like me, Olivia is the least, and Max, sweet, quiet Max, I just wanted to hold her hand through the chaos and help her get to the other side. Then rejoice with her over her accomplishments.
Reminds Me Of:
It reminded me a lot of 9 to 5 and The Devil Wears Prada–every bit as horrifying, rallying, and relatable.
What I Wish:
The only technical issue with this story is that I had trouble keeping names straight. I’m not sure why that was since the characters are very well-developed and utterly different. But, yet I did.
To Read or Not to Read:
If you are looking for a fast-paced, thought-provoking story that will have you cheering for the underdog, then this is one you will want to pick up as soon as possible.
Amanda Pellegrino is a TV screenwriter and novelist living in New York City whose writing has appeared in Refinery29 and Bustle. Smile and Look Pretty is her debut novel.
- Author Website: https://www.amandapellegrino.com/
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- Twitter: https://twitter.com/amandapellss?ref_src=twsrc%5Egoogle%7Ctwcamp%5Eserp%7Ctwgr%5Eauthor
The signs were always there. He was late to a few meetings. He started happy hour at 2:00 p.m. He promoted from within.
The signs weren’t noticeable at first. Until they were.
He was late to Marjorie’s meetings, not Ben’s. He offered scotch on the rocks to the guys. Most of his former male assistants were now editors.
It took years of working with him for Cate to learn those things. To realize they were signs.
But he had a reputation. That she knew from the beginning.
“You’ll need a thick skin,” he’d said on her first day. A warning.
She didn’t extend him the same courtesy.
Cate could tell you every book Larcey Publishing had ever released in its twenty-year history, and how old she had been when she first read it. The red LP stood out on all the spines in her dad’s “home office,” which was really the walk-in closet of her parents’ bedroom converted into a small library lined with bookshelves, the clothing rails outfitted with a plank of painted wood to form a desk. When she got home from school, she’d sneak into her parents’ room and read whatever book was on her dad’s nightstand that week—no matter how age inappropriate the title. By the time she was ten, she knew she wanted to spend her life helping people tell stories. Important stories that no one would hear otherwise.
Matthew Larcey was a literary prodigy, not just to her dad, but to the world. Before he was thirty, he was known as the next Maxwell Perkins and by thirty-five he used that acclaim to start his own publishing house. Jobs there were the only ones Cate applied to during her senior year of college. She started as a production assistant ten days after graduation, and when the position of Matt’s executive assistant opened a year later, she was the first to apply.
Matt’s assistant at the time was a lovely girl from Texas named Eleanor, who tried and failed to suppress her Southern accent. (Cate later learned Matt forbid y’all from conversations. Sign.) She interviewed Cate in a conference room with dull gray walls and two suicide-proof windows that looked out onto Sixth Avenue, forty-nine f lights below. Cate wore her go-to black dress with a leather trim and had prepped in the bathroom a few minutes before: whispering her elevator pitch while applying more mascara; detailing her current responsibilities as an assistant while running some Moroccan oil through her frizzy hair; listing her favorite books while swapping out f lats and a cardigan for heels and a blazer.
Twenty minutes into the interview, Matt Larcey walked in, wearing jeans and an AC/DC T-shirt with a small hole in the neck. Eyes wide, Cate and Eleanor watched him slowly sit down at the opposite side of the long conference table, typing on his phone. Despite having worked there for a year, Cate had never met the company’s founder. He wasn’t good-looking in the traditional sense—he was far too old for Cate anyway—but his salt-and-pepper hair paired with his tailored jeans emitted a kind of effortless power that Cate found enigmatic. She felt reassured knowing he had smile lines. Maybe it meant he wasn’t as difficult as his reputation implied.
Eleanor’s gaze darted to Matt and then back to Cate. “Um, as I was saying—”
“Did you tell her why you’re being replaced?” he interrupted, looking up at them. His phone buzzed against the table four times while Eleanor went as red as the LP on the company’s logo.
“I wasn’t available enough,” she said quietly.
Eleanor took a long breath and offered Cate a tight-lipped smile. “I was on vacation and missed an urgent email.”
Cate wanted to crawl under the table and come back when the tension was gone.
“If I’m working, you’re working,” Matt said. “That’s the deal.”
Seems logical, Cate thought. Sign.
“I know why you’re here.” He looked at Cate with an arched brow. “You’re a reader. Right? That’s what your Twitter bio says? You want to publish something that matters. The next great American novel, a book that will change the course of literature forever.”
Eleanor seemed to be shrinking in front of them, getting smaller and smaller with every word.
“If that’s what gets you through the day, great,” Matt continued. “By all means, try to find the next Zadie Smith. If you play by the rules, maybe you will. But there are a lot of others out there who would kill for this job. So don’t think you’ll get any favors. If you earn the book, you’ll get the book. Otherwise it will be you here picking out your own successor.”
When Eleanor appeared at Cate’s cubicle a few weeks later, offering her the job, Cate immediately accepted. Because she was a reader. She did want to find the next great American novel. And, despite its founder’s reputation, Larcey Publishing was the best place to do that.
Exactly two years later, Cate sat at her desk in the forty-ninth f loor bullpen, moving her eyes slowly across the f loor-to-ceiling color-coded bookshelves packed with LP titles, thinking about how she was officially the longest lasting assistant in Larcey’s history. When she had first started, each day she would look up from her desk at the wall of books in awe, like a tourist admiring the Chrysler Building, and dream about the day books she discovered and edited would join those shelves. Now, she had trouble remembering why she wanted to work there so badly in the first place.
She let out a deep breath. A wall of color-coded bookshelves was pretty to look at until you realized how painful it was to put together.
The executive assistants’ desks were located in the EAB, or Elusive Assistant Beau monde, as Cate called it before she got the job with Matt. It actually stood for Executive Assistant Bullpen, but hardly anyone knew that. To Finance they were Evil Annoying Babies; to editors, Eager Ass-kissing Brownnosers; and to Marketing, Expendable Agenda Builders. Whatever they were called, she was one of them. In the center of the rectangular room were two circular velvet couches around a glass coffee table with a bouquet of f lowers Cate was somehow in charge of buying and maintaining each week. Lining the perimeter of the room were seven desks, perfectly positioned outside each boss’s glass office so that each assistant was always being watched. Like fish in a bowl.
Cate glanced over her shoulder toward the shadows behind the now-curtained glass wall of Matt’s office, listening to the mumbles of the third editor in two months getting fired, and wondered—as they all did at that point—when she should expect the email from HR inviting her to meet them in Matt’s office at 6:30 p.m. on a Thursday.
Lucy, the CFO’s assistant, wheeled her chair toward Cate. “Maggie, huh?” she said, folding her long blond hair behind her ears as if that would help her gossip better.
“Seems that way,” Cate responded.
“Do you know what happened? I thought the self-help category was doing well.”
Cate shrugged. “I’m not sure.” She tried to look busy, maximizing and minimizing documents, opening and closing her calendar. Lucy was a great work wife, but she only got the job because her third cousin twice removed was Stephen King’s neighbor or something. This made her a “must hire,” thus untouchable. And Lucy knew it. She was more often found scooting across the bullpen in her white wheelie chair spreading rumors than actually working.
“Of course you know, Cate. You’re probably on the HR email.”
As Matt’s assistant, Cate was on all his emails. About the rounds of golf he planned next week. About every book that each editor wanted to acquire this season. About all the firings. She knew that Maggie, a self-help editor, was being fired for considering a position at Peacock Press. Not only were they Larcey’s main competitor, but Cate once heard a rumor that Matt dated its publisher in college, and she broke up with him in favor of his rugby-playing roommate. Either way, the rivalry seemed personal. They had offered Maggie $10K more and a nearly unlimited budget to acquire all the self-help books she could get her hands on. Cate knew everything. And that power was not something she was about to give up for Lucy. It was all she had.
“I guess self-help isn’t doing as well as we thought,” Cate said.
Before Lucy could reply, Maggie threw open Matt’s door. The entire room started furiously typing as Maggie stomped past the EAB, two suited HR reps scurrying behind her. Lucy picked up the first paper she could find on Cate’s desk and examined it so closely you’d think she’d just discovered the Rosetta Stone.
As soon as Maggie was out of earshot, Lucy said, “God, that was awkward.” She lowered her voice to a conspiratorial whisper. “I heard she’s going to Peacock.”
“Do you really think it’s Peacock?” Spencer Park whispered from his desk. “What, are they trying to poach everyone?”
“Poaching the people you want is more cost-effective than buying a company and paying for all the people you don’t,” Lucy responded. Cate could have sworn Lucy’s head cocked toward Matt’s office for the latter part of that statement.
Lucy returned to her desk and everyone went back to normal until a few moments later, when the heavy glass door behind her opened again. Cate didn’t need to turn around to know it was Matt leaving. Her back might be facing his office all day, but she knew his movements by heart. In the same way, she imagined, he probably knew hers.
Matt moseyed to the front of her desk, moving his worn, expensive leather briefcase from his right hand to his left. He’d been kayaking that weekend, and he always got blisters on his dominant hand when he kayaked. Cate hated that she knew that. “Why are you still here?” he asked, as if his I’m working, you’re working, that’s the deal speech didn’t play on a loop in her head 24/7. As if that wasn’t why she kept her phone on loud all the time, why she woke up panicking in the middle of the night about missing an email, and why she was that girl who showed up to bars on Saturdays hiding her laptop in her purse.
“Just finishing up some work.” Cate glanced at her nearly empty inbox. She was supposed to be on her way to The Shit List, a much-needed weekly vent session with her friends. Instead, she was going to be late. Not that that was unusual for her. If Matt was there, Cate was there, after all.
He looked at Cate, then at the other assistants, all furiously typing again to seem occupied. “Looks like everyone else is working a lot harder than you are right now.”
Well, I’m talking to you, Cate wanted to say. I stopped typing to talk to you.
What actually came out of her mouth was, “Have a good night.”
She watched him walk across the EAB and offer a wave and a smile to three executive assistants standing at the bookshelf, peeling some titles off the wall. “You all work too hard. This place would be in shambles without you,” he said to them before turning the corner toward the elevator bank.
After answering a few more emails, Cate poured some whiskey into her Bitches Get Stuff Done mug, grabbed her Board Meeting Makeup Kit out of the bottom drawer of her desk and walked into the bathroom. She was already going to be fifteen minutes late to The Shit List; what was another fifteen to look presentable and rub some slightly off-colored concealer on the under-eye circles that seemed to grow darker throughout the day?
She had discovered the necessity of a makeup kit on her second day as Matt’s assistant. He had a board meeting, which was one of the only times she saw him in a suit.
“At exactly four fifteen, I need you to come into the meeting and bring me a cup of coffee,” he said. “Just put it in front of me and walk out. Don’t look at me. Don’t look at anyone. Just in and out. And, you know—” he looked her up and down “—look…presentable.”
Cate could feel her cheeks flame as he walked away. She didn’t wear a lot of makeup, but she did always at least look presentable for work.
“Here,” said the CMO’s assistant at the time. She dropped a small pink-and-white Lilly Pulitzer bag on Cate’s desk. “That’s code for put on some makeup.”
“I have makeup on.” Cate rubbed her cheek as if the pressure from her fingers could force blush to suddenly appear.
She nudged the bag forward. “Not the kind men notice.”
Reluctantly, Cate unzipped it and inside found one of everything: powder foundation, mascara, eyeliner, eye shadow, blush, red lipstick. No variety. Bare minimum to look like the maximum.
“Put it on my desk when you’re done. You should keep a board meeting kit here, too. This won’t be the only time you’ll need it.”
After two years of board, author, and literary agent meetings, dropping things off at home for his kid, picking his wife up in the lobby, and countless other occasions for which Cate was told to “look presentable,” getting ready for margaritas with her friends was the only time she used the kit to show herself off, rather than be shown off.
Happy two-year-work-aversary, Cate thought to herself as she put her makeup bag back in her desk. She took another look at the bookshelf on her way out. Two years too many.
The weekly calendar invite for The Shit List pinged on Cate’s phone as she darted up the Union Square subway staircase. The late May humidity combined with 6-train rush hour crowd left small beads of sweat on her upper lip and made her curls wild and frizzy. She passed the produce market closing up shop for the night and the men playing chess under the streetlights.
When Cate arrived at Sobremesa, she waved at the hostess and then at their favorite bartender as she beelined past the crowded bar to join everyone at their usual booth in the back. Sobremesa was a strange place: corporate but lowbrow. That was strategic. Find a bar where they were the only group under forty so no one around would recognize their bosses’ names when Lauren said Pete, an Emmy-winning screenwriter, had been avoiding her all day; or Max complained that Richard, a morning news anchor, had stared at her butt for the entire live shoot; or Olivia yelled about Nate, a washed-up actor who refused to realize he was no long relevant. They didn’t need their work gossip on Page Six.
Cate stopped when she saw the three of them in their usual spot, laughing at something Olivia said, a half-empty pitcher of spicy margaritas moving between them. Lauren was squinting through her black-rimmed glasses, always refusing to consider a new prescription until she got promoted and could afford the co-pay. Olivia’s topknot bounced side to side on her head as she spoke enthusiastically with her hands, one of her dramatic tendencies as a budding actress. Max sat in the corner, plucking salt crystals off the rim of her glass and licking them off her pointer finger.
“Wow,” Lauren said when she spotted Cate.
“What?” Cate sank into the booth next to her. Lauren was making too much eye contact, the way she did when she was annoyed. Max poured the remainder of the pitcher into a fourth glass and pushed it toward Cate.
Lauren took a long sip from the tiny straw before saying, “Nice shirt.”
Shit. Cate was wearing Lauren’s top. The black T-shirt she told Lauren she’d wash and return to her closet three wears before. The one that now had semipermanent white deodorant circles under the armpits and was ever so slightly stretched out around the chest to fit Cate’s larger cup size. “Sorry,” she said to Lauren, who would hold a grudge until the freshly cleaned and folded shirt was back in her dresser. It would be at least a month before Cate could borrow anything from Lauren again, which was a bummer because she’d had her eye on a black pleated midiskirt for a date next week.
“Whatever,” Lauren said with a sigh. “Should we just start?” She motioned toward the waitress and, when she arrived, ordered another pitcher of margaritas in Spanish.
In the center of the table was a small stack of cash to which Cate added her five-dollar contribution. She ripped a napkin into quarters and handed them out, scribbling onto the thin paper, the words bleeding together. I booked Matt’s $37,000 first-class tickets for his family’s Kenyan safari an hour after realizing that unless I get a raise or my student loans disappear into the ether, I can’t afford to go home to Illinois for Thanksgiving for the fourth year in a row. Then she crossed out the latter half. No one she knew could ever afford to leave New York then, which was why the four of them always ended up doing Friendsgiving instead. It wasn’t the same as cooking with her mom and then watching her dad unbutton his pants to fall asleep in his La- Z-Boy in front of the football game, but it was something.
After everyone finished scribbling on their napkins, the storytelling began.
Lauren complained about wheeling an industrial printer covered in blue tarp from the writers’ trailer to Pete’s trailer parked four long city avenues away during a thunderstorm. Then, upon showing up to work drenched, was asked by one of the writers to get coffee for everyone since “she was already wet.”
Olivia had spent an entire day this week trying to sneak into the W Hotel Residences by schmoozing a young security guard so that she could do Nate’s laundry there because he liked the smell of their detergent. “It’s The Laundress,” Olivia said, rubbing her temples as if the mere mention of the brand’s name gave her a headache. “It’s what he uses too. Bought it for him myself. But he insists it’s different.”
Max had to pretend Sheena’s five-year-old son was hers so she could pick up his ADD medication before the anchor’s weekend getaway to a resort in New Mexico. The pharmacist had seemed skeptical, but Max couldn’t return to the newsroom without it. “I made a comment questioning how we still live in a world where young motherhood is challenged,” Max said. The pharmacist had stopped asking questions.
The best part about their four-year friendship, Cate found, was the lack of explanations. They didn’t have to preface names in their stories with “my boss” or “my friend” or “the cashier at my bodega.” They never needed to fill anyone in on what they missed. Because they didn’t miss anything. They knew everything about each other’s lives. Cate knew that Lauren hadn’t brought a guy home in at least a year and hadn’t had sex in at least that long as well. She knew that Olivia rolled her eyes at her Southern Peachtree roots but would secretly perk up whenever a familiar accent was within earshot, reminding her of home. And Cate knew that Max’s parents wielded enough old money power and privilege to get her promoted anywhere, but Max insisted on earning it herself.
Knowing everything about her friends also meant knowing everything about their bosses. Lauren’s boss kept bottles of tequila, whiskey, and gin underneath the couch in his trailer. Cate could tell by looking at a paparazzi photo of Olivia’s boss in People Magazine whether it was a coincidental shot or he had Olivia tip them off about his whereabouts. Cate could recognize by Max’s outfit whether she expected Richard, the handsy morning anchor, to be in the office that day.
Once all the stories were told and the napkin scraps circled the tea light on the table like a strange sacrificial ceremony, Lauren said, “Can I make the executive decision that Olivia wins?” Everyone agreed; folding your boss’s stiff boxers, regardless of how good they apparently smelled afterward, should win you more than twenty dollars.
Cate took the piece of napkin in her hand and looked down at her chicken scratch handwriting. This was her life. These were the things she spent her days doing. It was her two-year anniversary as Matt’s assistant, and the day went on just like any other. Cate wasn’t expecting a cake with her face on it or anything. But some kind of acknowledgment would have been appreciated. Something that said couldn’t do it without you or I hope these two years have been worth it or, at least, a simple thank you.
What did Cate learn about the publishing industry from booking Matt’s vacations? What did she learn by organizing the papers on his desk in alphabetical order? What did she learn from spending a week every November opening up his cabin in Vermont for the season? She did learn that he spent $600 every year on a new Canada Goose coat; that the couch in their basement was incredibly uncomfortable to sleep on; and that his wife kept a dildo in the bottom drawer of her nightstand (but what did Matt expect, sending his poorly-paid assistant to his rich vacation house?).
And what had happened while she’d been 340 miles north, spraying salt all over the cabin’s front walkway? Spencer filled in on Matt’s desk and was asked to “sit in on” three author meetings and one board meeting. She’d met only one author in two years, and the closest she came to board meetings was delivering coffee with strict instructions not to speak. Did anyone tell Spencer to “look presentable”?
For the last two years, Cate had only focused on what was at stake: money, access to stamps for mailing rent checks, free food after author meetings, a foot in the door for her dream job. But it was starting to feel…fine. Uninspiring. Empty. What was she working toward?
Cate took one last look at the napkin before dipping the bottom right corner into the tea light’s f lame. She held it between her fingers, watching Matt Larcey’s name burn in her hand as the text slowly turned to ashes and fell onto the wooden table.
After she swept the ashes to the f loor, Cate held up her margarita. “Here’s to the day when we can make money without doing something degrading.”
Their glasses met in the middle, and Cate looked at her friends, the assistants busting their asses, making the rules from behind the scenes. What if they all got together? What if they called bullshit?
What if they all said no?
Excerpted from Smile and Look Pretty by Amanda Pellegrino, Copyright © 2021 by Amanda Pellegrino. Published by Park Row Books.