True Story: The Perks of Being a Wallflower

On Episode 55 of the podcast, I had the opportunity to welcome my friend Caitlin Flynn to SSR! If you’ve already tuned in to the show, you know a little bit about our history — I met Caitlin in an HR orientation session on my very first day of work in the “grown-up” world when I started my publishing job right out of college. Caitlin was the only one in the room who looked like she might be close to my age (saying this sounds silly in hindsight, but at the time, it felt like something that could be really important!), and we started making small talk. She could probably tell that I was nervous, all dressed up and ready to go in the blazer my mom had bought me at J. Crew after graduation (for the record, I was wayyyy overdressed). It turned out that Caitlin and I had been hired into the same group, and that our cubicles would be next to each other! I was so relieved. It felt good to walk out of the orientation and into my workspace with someone who I knew, someone who could turn into a friend. All you introverts out there know what I’m talking about.

Caitlin and I sat within a few feet of each other for about three years, until I moved to a different part of the company. We saw each other through professional victories and low points. We compared notes on the best Thai takeout menus in New York. We drank too much at more than a few team happy hours. Caitlin was a few years ahead of me in her career, and she helped me navigate the transition from college to corporate life — and years later, she was also the person to help me navigate the transition from corporate life to freelancing! She left our company about a year before I started considering doing the same, and her experience with becoming a full-time writer really did inspire me to go for it. She made me believe that I could do it! I definitely wouldn’t be making a living as a full-time writer, editor, and content creator — and I probably wouldn’t be making the SSR podcast, either! — without Caitlin’s encouragement.


I’ve been hoping to have Caitlin on the podcast for a long time, and I’m so glad we were finally able to make it work for this episode, on which we talk all about Stephen Chbosky’s The Perks of Being a Wallflower. When I offered this book to Caitlin as an option, I had genuinely forgotten that it was one of her favorites (and I’m sure I knew this at some point, because we did a lot of book talking back in our publishing days!), but the fact that the story is so close to her heart made this such a rich, thoughtful conversation. I’m so grateful for Caitlin’s perspective!

I prepped plenty of notes on Perks, and didn’t get to share all of them in the episode, so I’m comin’ atcha with a few more thoughts about the book in today’s True Story.

(For context, you can listen to the episode here and get a refresher on the book’s plot here!)

Sam and Patrick are the kinds of friends I always wanted to have, and I think they probably represent that for many young readers.

When we meet Charlie, he’s anxious to connect with anyone. He’s just come through the tragic loss of his best friend Michael, making the beginning of high school even scarier and lonelier than it would have been otherwise. He meets a senior named Patrick in shop class, then says hello to him at a football game… and just like that, Charlie is welcomed into Patrick’s group of friends. Patrick’s stepsister Sam is, of course, the figure that looms largest for Charlie in this group, since he’s essentially crushing on her from the moment they meet.

This friend group is fun and unique. They aren’t afraid to do their own thing. They stick to traditions, like their attendance (and sometimes performance!) at The Rocky Horror Picture Show. They listen to cool music. They seem to be generally well-known and well-liked among the student body, but they don’t seem particularly concerned with what others think. They aren’t afraid to be honest with each other, like when Patrick advises Charlie to stay away so things can get back to normal after his weird fallout with Mary Elizabeth.

As a high schooler, I dreamed of having friends just like this, and I’m sure I wasn’t alone. I could imagine being swept up in Patrick and Sam’s group just like Charlie had been.

I was fascinated with Charlie’s relationship with his older brother.

Maybe it’s because I, like Charlie, was born and raised in Pennsylvania and know very well the power of high school football culture in many parts of the state, but I was really interested in Charlie’s (nameless) big brother. We learn that he’s recently started his freshman year at Penn State, where he was offered a football scholarship. Where I grew up, this was basically the ultimate goal for many of my classmates. You’d fall and kiss the feet of anyone who secured this kind of scholarship!

As a result of my own experience, I think I may have read more into Charlie’s brother than the author even wanted readers to! I could feel Charlie’s admiration for him and the sheer weight of the opportunity that had been offered to him. I could only imagine how much Charlie’s brother was considered a golden child in their household, and how that must have affected Charlie’s self-esteem and feelings about his family. It also seemed to play into Charlie’s views of what it means to be strong, tough, and masculine. We see him try to step into that kind of strength when he gets involved in a physical altercation in the cafeteria to defend Patrick! He’s able to do it because he learned to fight from his brother.

I think it’s really interesting that this book has been on required reading lists for certain school districts.

When I shared on Instagram that I was reading Perks for the podcast, I heard from several teachers who said they were frustrated that the book had recently been removed from their schools’ curricula. I had never heard of it being on a required reading list, but I did a little research… and it turns out that it has, and for many school districts!

I think I’ve made it pretty clear by now that I’m definitely not in favor of censorship (and certainly not banning books from school libraries), but it did surprise me that The Perks of Being a Wallflower would be part of a high school English course’s curriculum. As we discuss on the episode, the book is chock full of sensitive issues that could be triggering or upsetting to a lot of students. I can understand why parents might be concerned about their children reading some of this content, even though I believe every teen should get their hands on it at some point.

Truthfully, I really do wish we’d known who Charlie was writing the letters to.

Caitlin and I spent a few minutes on this week’s episode chatting about the format of Perks. As you might remember, the book is told in a series of letters from Charlie, but we’re not sure who he’s writing to! In our conversation, Caitlin speculated that Charlie is meant to be writing to us as the readers, generally, and that the specific recipient doesn’t really matter. I tend to agree with her, but that doesn't mean I didn’t find myself wondering every few pages if I should be thinking about someone else being on the other end of Charlie’s messages! I kept looking for context clues, trying to figure out if the book was a very specific kind of mystery novel in which I was expected to guess which of the characters the protagonist was addressing. It might just be the way my brain works, but the lack of clarity on this was a little distracting for me.

I think it’s important that kids read stories about high schoolers who have complicated relationships with/crushes on their friends.

Charlie admits to Sam that he has feelings for her pretty early in their relationship. She doesn’t return those feelings, and instead spends much of the book pursuing older guys (who don’t treat her well). At the story’s conclusion, she tells Charlie that she didn’t want him to have a crush on her. She didn’t want to be idealized! She wanted him to learn about her as a real, flawed, complicated human before deciding how he felt about her. They do kiss after this conversation, which triggers the long-repressed memories of Charlie’s childhood sexual abuse.

Having been through high school and experienced complicated feelings about some of my close friends, I really appreciated this illustration of the push/pull that happens when there’s unrequited love in your social circle. I think it’s especially meaningful that Chbosky chose to bring Sam back as part of Charlie’s support network after he decides to get psychological treatment to address his childhood trauma. Even after their intense conversation and physical encounter, Sam is able to put aside any awkwardness and show up in her role as best friend. So many teenagers — and adults, too! — can relate to this kind of relationship, and I’m sure it gave young readers hope to see that their crush might remain a friend unconditionally.

I think this is one of the best book titles. Like, ever.

The Perks of Being a Wallflower?!?!? Seriously?!?!? Such a good title. I remember hearing it for the first time as a teen and thinking, “Wow! That sounds cool. I need to find out what that’s about.” It’s so evocative and funky and generally GREAT.

Listen to the podcast episode about The Perks of Being a Wallflower here!

I can’t wait to hear your “true story” thoughts about this book. Share them with me in the comments below.

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