Celebrating the (Not So) Sweet Sixteen of Sloppy Firsts

I wasn’t old enough to meet Jessica “Not-So” Darling when she first arrived on the scene in 2001—the fictional protagonist of the eponymously named series was 15, and I was only 11—but thankfully Megan McCafferty’s Sloppy Firsts was waiting for me when I got to high school. And I fell in love.

The book is sixteen years old today, and it still holds up to fresh reading. The first thing that hooked me was the fact that the novel is told as a series of diary entries and letters to Jessica’s best friend, Hope, who has just moved away. Yes, please! I’m a sucker for epistolary novels, and the format offers the perfect way to dive into Jessica’s voice and to see the way she thinks and interacts with the world. Are those thoughts all rainbows, butterflies, and well wishes for her peers? Of course not. Her voice is a pitch-perfect example of middle-class teenaged misery.

McCafferty gives equal weight to all aspects of Jessica’s life: her romantic prospects (or lack thereof), school stress, family drama, her struggles with the friends she’s left with now that Hope has gone—the major focus of Sloppy Firsts, in fact, is Jessica grappling with the fact that she may actually hate all the people she calls her friends. And then there’s the intriguing Marcus Flutie, the class “dreg” (and OG book boyfriend) who keeps popping up in her life. But can Jessica let herself get close to him when he may have been one of the burnout enablers of Hope’s brother, who died of an overdose?

The development of Jessica and Marcus’s maybe-relationship is the book’s irresistible heart. Did I track my own relationship with my own high school semi-slacker against it? Yes. Do the fictional characters have a happier ending than we did? I’ll let you find out for yourself! But trust me when I say McCafferty makes every bend in their story feel so very real.

And that’s the true joy of the Jessica Darling series. There’s something so relatable about the trainwreck that is Jessica’s life. She struggles to accept herself while refusing to conform to anyone else’s idea of who she should be. She doesn’t shy away from topics like her growing interest in sex or the prevalence of underage drinking among her peers, and a running arc throughout her fictional debut is the stress-related disappearance of her period. She’s certainly not perfect—Jessica falls prey to the same kinds of self-sabotage that cause so many of us to make terrible decisions, like blowing up perfectly good friendships or getting bangs—and that’s okay. She’s the poster child for screwing up and falling down and still, somehow, making it to the other side.

Jessica Darling is the sarcastic, sharp-witted, occasionally self-absorbed best friend many of us have, wish we had, or see in ourselves. She can be infuriating, self-righteous, self-destructive, but she’s always real.

So happy birthday, Sloppy Firsts. And here’s to many more.

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