A Recurring Read: The Jessica Darling series

Hello my wonderful readers! Nikkie here with that bookish babble you love so much. Or potentially just tolerate . . . Oh well. You’re here, aren’t you?

Today, I want to shine a light on one of my favorite book series: Megan McCafferty’s Jessica Darling series. I actually wrote a post about these books back when this blog was Lit’s Not Dead, but since that post is no more—and September marks the 15th anniversary of the publication of the series’ first book, Sloppy Firsts—I figured “Why not do a new, updated post?”

I basically only remember one thing from the original post I wrote: I focused a lot on the parallels I drew between the main love pairing in the series and my relationship with my high-school boyfriend. That’s still relevant and will likely come up when I talk about my difficulty rereading the fourth book in the series, but this post will offer up a bit more than just “It reminds me of high school.”

So stick around; let’s have some fun!

I honestly don’t remember the exact time that Sloppy Firsts and its sharp-witted protagonist Jessica Darling came into my life. I know it was high school, and I suppose I had to have been 15 or 16 since I connect it so heavily with the guy I dated during the last two years of high school. But a specific time doesn’t spring to mind. What I do remember is that I stumbled across it shortly after I decided that I was old enough to start perusing the Fiction and Literature section at Barnes and Noble. I wasn’t ready to fully abandon YA (and I still haven’t), but I figured I’d better start seeing what else is out there. My first foray was actually Hairstyles of the Damned by Joe Meno, and I loved that book, so I seemed off to a good start. Plus, that book was about a high schooler, so it was a pretty good transition into “adult” reading.

Jessica proved to be the best transition . . . insofar as you can transition into reading a new category of fiction without giving up on the old categories. The series begins with Jessica’s sophomore year of high school and ends several years removed from her college graduation. Though in actuality Jessica would be a bit older than me (she’s in high school for Y2K whereas I was in the fifth grade), her story came to me at just the right time. As much as I loved growing up with Harry Potter, he had a few more things to deal with than I did—evil overlords and Chosen One status and all that. It was nice to have someone who lived in a real world (and had boobs) to guide me through the horrors of mid- to late adolescence.


I instantly loved Sloppy Firsts. Jessica Darling was a girl after my own idealized version of my heart. She was introspective and weird and constantly journalling (this is when I realized how much I love epistolary novels). But she was sporty like I wished I could be, she was bold when it counted, and when she no longer felt like conforming to people’s idea of her, she just did her own thing. She also had actually interesting things happen to her while maintaining an “everyday teen” vibe. Her best friend’s older brother died of a drug overdose. Said best friend (Hope) has now moved far away, and the remaining friends (Bridget, Sara, and Manda) are kind of the worst. A new friend who ends up being a secret heiress and writes a “tell-all” fiction book about her experiences in a New Jersey public high school. A druggie who used to party with Hope’s brother suddenly starts popping up all over the place, messing with Jessica’s mind. Oh, and she shares her name with a popular (fictional) porn star. Her life is kind of insane!

Of course, the crux of my interest in this series is Marcus, the  druggie who knew Hope’s brother. As much as the series is about Jessica growing and finding herself (and realizing that sometimes people aren’t as terrible as she assumes they are), it is also about the ebb and flow of her relationship with Marcus. He was mysterious and frustrating and the kind of attractive that sneaks up on you. As ridiculous as he was, it was hard not to fall for him (and I’m not just talking about Jessica).

As mentioned earlier, part of the reason I connected so deeply to the series was that the Jessica+Marcus of it all heavily reminded me of my life with my own druggie boyfriend. Thankfully, the demise of my relationship had no effect on my love of the series! But as it stood, back in high school and the first semester of college, I was desperate to see if a relationship between people standing on different sides of the “drug taker” line could actually work. As you know, mine didn’t, but there was hope for my beloved protagonists.

It’s weird that that became a major driving force for my interest considering Marcus is no longer a druggie in the second book, Second Helpings. In fact, he’s a straight-edge genius because he’s one of those “wasn’t living up to his tremendous potential” types; he also likes gimmicks (boy band shirts, Day of the Week shirts, etc.). Now, he’s not faking his intelligence—that’s legitimate—but in a very Jessica fashion, he decided to subvert everyone’s expectations and get his shit together. But given the way he and Jessica blew up at the conclusion of Sloppy Firsts, this turn-about doesn’t really improve his stature in her eyes. In fact, she moves on to the class nerd-turned-hottie, Len . . . who becomes Marcus’s best friend, so unfortunately Jessica just can’t get away from him. Especially not when he volunteers at the elderly home that houses her spunky grandmother. At least Jessica has other things to distract her, like worrying about applying to Columbia in the wake of 9/11 or convincing her parents to pay for it after she decides to go or still trying to relate to Bridget, Sara, and Manda (though Bridget is by far the best of the bunch).

Because Megan McCafferty wanted High School Me to be horribly depressed, she couldn’t let the Jessica+Marcus happiness from the end of Second Helpings last for too long. In Charmed Thirds, their relationship is shaken by Marcus attending an unconventional school out in the desert (where he winds up taking a vow of silence that means he only sends cryptic postcards) and a pregnancy scare that Jessica takes a long time to acknowledge. It was very much a roller-coaster for me to deal with since I got heart-eyes every time I thought about Jessica and Marcus together. How dare some pseudo-intellectual douchebag think he’s at all worth Jessica’s time! Prick.

Thinking back, I feel like there really isn’t that much focus on Jessica’s schooling in Charmed Thirds. I could be wrong, as it’s been several years since I’ve read the third book, but the things that spring to mind are the guy she randomly hooks up with who becomes obsessed with her and then dies; Marcus’s one-worded postcards; and the pseudo-intellectual douchebag. Oh! And this older guy who she considers having an affair with.

You know, Jessica gets a lot of things done in this book, now that I think about it . . . Does it span the entirety of her college career? It’s quite possible! As implied, I am quite fuzzy on the events of this book. The (former) friend who wrote the tell-all book? She shows up again, but I can’t remember if it was in Second Helpings or in Charmed Thirds or both . . . Oh, whatever, you guys. I’m not perfect! Ah! And Jessica goes to see Marcus’s parents to try and understand why he’s doing the cryptic postcard thing.

Despite all the drama, Marcus and Jessica live to see another day. But, don’t be fooled; Fourth Comings starts with Jessica deciding to break up with him. I know—this girl really needs to get her act together when it comes to Marcus. Anyway. He flips the script by proposing to her, so the book takes place over the week he gives her to respond, detailing the thought process that led to her final answer. During that time, she chronicles recent fights they’ve had and how her experience living with Hope and Manda (don’t even get her started!) ends up being a major influence.

Considering how I prefaced this post by saying that I have a difficult time with this book, it should come as no surprise to you that Jessica turns down the proposal. Again, despite all the mounting evidence, I saw Jessica and Marcus as a reflection of myself and my then-boyfriend (a relationship that was quickly finding its way between a rock and a hard place). So the fact that Jessica decided her love for Marcus wasn’t enough to combat what she felt were insurmountable circumstances was just too much for my poor, hopeful little heart to handle.

Was it crazy for me to believe that my relationship’s future was being spelled out in the pages of a book? Probably. But that’s what happens when you’re a book addict such as myself! You get invested, you get your heart broken, you think that the author is telling you your life’s story but dressing it up in the style of a white girl from New Jersey.

What also made it really hard for me to accept this book was because Megan McCafferty implied that it was the last book in the series. I had to live with the end of my OTP (one true pairing) being canon?!

Turns out I didn’t.

McCafferty surprised us all when she gave us Perfect Fifths. It literarily saved my life! Because not only did I get Jessica and Marcus back, I actually got to be in Marcus’s head! That’s right. Marcus became a POV character. It was awesome. Finally, a potential satisfying conclusion!

Now, at that point, it was already too late for me and my pseudo-Marcus. Perfect Fifths came out in April 2009; I’d semi-officially broken up with my boyfriend over Thanksgiving break 2008. While there were still miscellaneous strings that took a while to dissolve (into the summer, actually), I didn’t pick up the book assuming that it was going to give me the solution to my post-breakup problems. Was I a little swayed by the fact that the book takes place a few years after Fourth Comings, thus making it the perfect time for Marcus and Jessica to reunite and see if they could handle giving it one more try? Probably. But I was 19 at the time, and a few months away from meeting Super Hubs. Let Younger Nikkie dream a little!

Regardless of its (lack of) effect on my relationship status, this book was so amazing! Seeing the characters you’ve loved for years FINALLY air out their dirty laundry and really dig into their past was just so gratifying. I’m someone who holds onto things for years and wonders what would’ve happened with old friends if either one of us had just gotten over ourselves and apologized. Thus, I was deliriously happy that McCafferty didn’t let Marcus and Jessica fall victim to that kind of pigheadedness. While I’m hyper-aware that very few high school sweethearts make it past high school (and the whole on-off thing isn’t super sustainable or a great foundation for a lasting relationship), the whole point of loving to read is that I love to escape. Even when I pick books that are realistic, I can still hope for a happy ending because their fictional lives HAVE to turn out better than real ones, right?

This series means a lot to me, which I hope was conveyed even though I mostly just told you about what happens in it. It really was and is very special to me. It was a guiding light into what would become the ridiculousness of almost-adulthood. I should have paid closer attention because I still feel insufficiently prepared for all the crappy aspects of adult life. Jessica’s snarky voice was the inner bitch I wanted to let out, but given how many years I spent being other people’s Yes Woman, I didn’t feel comfortable trying out such a radical change in personality. So I lived vicariously through her, and it seems like that was a pretty good choice.

I think the thing that really stuck out to me is that even when Jessica was struggling to figure out who she was, she never really did anything that wasn’t her. She DID continue with track even though she hated it, but that spoke more to her perfectionist needs and desire to get into a top-rate school . . . and just a pinch of “This is what connects me to my father.” Jessica was always 100 percent, definitively Jessica Darling, and I wish I could say the same about myself.

I think I’m getting closer though . . . I should check in with Jessica and see what she thinks.

May your TBR piles tower but never topple,

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