Literature / Jessica Darling

The Jessica Darling series of novels by Megan McCafferty are tragicomic slice-of-life stories chronicling the life of their smart, cynical and perpetually gloomy eponymous protagonist from her sixteenth birthday up through her mid-twenties. Along the way, she tries to figure out her place in a world that constantly strikes her as bizarre, suffers a number of demoralising setbacks and lessons in humility, and enjoys an on-again, off-again relationship with reformed bad boy Marcus Flutie.

The story is told partly through journal entries, partly through letters Jessica writes to her best friend Hope, who moved to the other side of the country just before the start of the first book. As such it is prone to instances of Unreliable Narrator, but also to a lot of Jessica's hilariously scathing takes on other people's, and her own, follies and dysfunctions.

There are five books in the main series:

  • Sloppy Firsts
  • Second Helpings
  • Charmed Thirds
  • Fourth Comings
  • Perfect Fifths

McCafferty has also written three prequel novels, dealing with Jessica's earlier teenage years:

  • Jessica Darling's It List: The (Totally Not) Guaranteed Guide to Popularity, Prettiness & Perfection
  • Jessica Darling's It List 2: The (Totally Not) Guaranteed Guide to Friends, Foes & Faux Friends
  • Jessica Darling's It List 3: The (Totally Not) Guaranteed Guide to Stressing, Obsessing & Second-Guessing

Provides Examples Of:

  • A-Cup Angst: Jessica often bemoans her "A-minus cup" bust.
  • Adorkable: Jess claims to prefer guys who are "geeky-cute." Her actual dating track record casts some doubt on that, though.
  • Big Beautiful Woman: Jessica notes that for all the effort she spends on trying to diet them away, Sara actually looks a lot better with her extra pounds than without them.
  • Bigger Is Better in Bed: Jessica's opinion, as expressed in the third book, is that while she isn't sure if it's better per se, it sure doesn't hurt.
  • But I Would Really Enjoy It: Towards the end of the first book, Jess writes a list of reasons why she should and should not sleep with Marcus. The "should not" list has a lot of items on it. The "should" list has a single one:
    I want to. Oh, God, do I want to.
  • Character Development: A running theme of the series is that people keep changing, and that holding on to fixed impressions of what they're like is a mistake.
  • Children Raise You: Bethany actually matures slightly after having a daughter. Slightly, mind you.
  • Cool Loser: Jessica gets called out on being one by a lot of other students in college, who were genuine losers in high school and aren't impressed by the fact that while she was objectively pretty successful, she still always felt pathetic and miserable.
  • Cool Old Lady: Jessica's grandmother believes in making the most of retirement home life.
  • D-Cup Distress: Manda claims to hate her well-developed bust. Jess grumpily notes that that doesn't stop her from always wearing borderline-Stripperific clothes that show it off to best advantage.
  • Dogged Nice Guy: Scotty spends the first book being this. In the second book, he drops the Dogged part. And sadly also the Nice Guy part.
  • Do You Want to Copulate?: Len tells Jess out of nowhere in the third book that he thinks they should have sex. He means for it to come across as suave and laid-back, but though she finds it somewhat charming, it's for other reasons.
  • The Eeyore: Jessica just can't seem to help being miserable, no matter where she is and no matter how well things seem to be going. Others frequently accuse her of never being satisfied, and she spends a lot of time wondering just what's wrong with her.
  • Embarrassing Nickname: Jessica's father likes to call her "Notso" as a non-too-subtle comment on her prickly disposition - as in, "Jessica Not-So-Darling." Jessica, possibly proving his point, is not amused. She also hates being called "Jessie," preferring either "Jess" or "Jessica."
    • Sara, who is sensitive about her weight, does not enjoy being called "Bruiser."
    • Manda would probably not be happy to know that Jess and Hope have referred to her, between the two of them, first as "the Kissing Slut," then as "Lend-A-Hand-A Manda," and most recently as "The Headmaster," as her sexual repertoire has grown increasingly advanced.
    • Marcus was known as Krispy Kreme in high school, though he doesn't seem to have let it get to him. (and it was at least half a compliment of sorts) note 
  • Erudite Stoner: Marcus, until he cleans up. Bridget claims that Jessica just generally tends to go for boys of the "stonah lovah" variety.
  • First Person Snarker: Jess, of course.
  • Good Bad Girl: Manda thinks she is this and that her promiscuity is a sign of her refusal to bow to patriarchal sexual norms, but Jessica is definitely not convinced. Later played more straight with Jessica's college friend Dexy though in her case, her zest for life turns out to be a coping mechanism to stave off clinical depression, but on the whole, Jessica doesn't think much of girls or guys who she sees as oversexed.
  • Good Girls Avoid Abortion: Averted. When Jessica briefly worries that she's pregnant in book three, she knows all along that she'll have to get an abortion if she is. In theory that's because she's on a medication that causes fetal deformities, but she admits to herself that it wouldn't matter if she weren't - at age nineteen, she's just not anywhere near ready.
  • Happy Ending Override: The main theme of the third book. The second book ends with Jess finally graduating from the high school she thought was hell, about to leave the small town where she felt Surrounded by Idiots to move to the big city and attend the college of her dreams, and in a relationship with a guy she's crazy about. Then Reality Ensues and life after high school turns out to be even harder and more confusing, just in other ways. Jess spends a lot of time in the third book ruminating on just how stupid she was to think that everything would be smooth sailing from now on.
  • Hes All Grown Up:
    • Percy gains a lot of height and a generally more manly appearance over the summer, which shocks Jessica, who's gotten used to thinking about him as that weedy kid with a Precocious Crush on her.
      This wasn't Pepe le Pew. It was Pepe le Puberty.
    • Len manages to lose his zits between junior and senior year. To Jessica's surprise, it turns out that there was a complete hottie hiding beneath them. The effect is somewhat ruined by his personality remaining the same, though.
  • High School: The setting for the first two novels and the prequels, which as usual for the trope treat the high school drama as Serious Business. That part is subverted in the third, though, much of which is devoted to Jessica being astonished at how little it all turned out to mean once she got out into the real world.
  • Incompatible Orientation: Happens to poor Jess more than once.
  • It's All About Me: Bethany starts out this way, until she has a baby and broadens her horizons a little. At which point she promptly turns around and accuses Jessica of being this way.
  • Jerk Jock: Scotty turns into one in the second book. At one point, he claims that he doesn't actually want to be one, but it's the only way to get laid, and getting laid is the one thing a guy must do. Jessica is less than sympathetic.
  • Manly Gay: Paul, as it turns out.
  • The Matchmaker: Jessica's mom is forever dropping unsubtle hints about how Jessica should really take more interest in one guy or another, he's really quite a catch and I think he likes you, you know, and anyway you can't be too choosy or else you'll be alone forever. Jess, needless to say, is not appreciative of her efforts.
  • No Periods, Period: Averted, Jessica's period gets mentioned on occasion, though mostly for its absence. Apparently she's prone to not getting it when she's going through a stressful time, which she finds upsetting in the first book and even more so when it happens again in the third - because she's sexually active at the time, and at first she's terrified that she's pregnant.
  • Old Shame: Hy ends up feeling this way about her book about Jessica and her friends, and is grateful when the movie version ends up in Development Hell.
  • Once a Season: Each of the first three books ends with Jessica and Hope meeting up.
  • Parents as People: Jessica's parents are far from perfect, but they try.
  • Pregnancy Scare: Jess has one in book three, though it takes place between chapters and is told in retrospect.
  • Reality Ensues: Quite often. In one notable example, Jessica has been working as a tutor for a group of neurotic high school over-achievers to help them choose and get into the right university. Finally, after one too many snotty comments about how anyone who didn't go to Harvard has failed at life, she snaps and goes on an absolutely magnificent rant about how none of what they think is important now is going to matter in a few short years, how their problems and concerns are ones that only spoiled upper-middle-class brats care about, and how even if they by sheer accident make all the right life choices they might still end up failing or dying, because Life Isn't Fair. Then, right at the heels of that, the chapter ends with:
    I got fired, of course.
  • Sex Is Evil: Len believes that young people should just not have sex, not for any particular moral reasons but because they're not ready to face the risk of pregnancy and sexually transmittable disease. In the third book, he turns out to have lost this along with his other youthful certainties, and Jessica ends up taking his virginity.
  • Slap-Slap-Kiss: Jessica's relationship with Kieran in the third book is the epitome of this, to the point that we at one point see them undressing each other while arguing heatedly about philosophy.
  • The Snark Knight: Jessica.
  • Soapbox Sadie: Paul joins a protest group made up entirely of these in college. Jess is initially excited to meet them, but is quickly put off by their self-righteousness and the way they seem to be against absolutely everything.
  • Suddenly Sexuality: Manda, supposedly. Jessica suspects that her sudden turn from boy-crazy to lesbian is just the last version of Manda's habit of using her sexuality to make a questionable political statement.
  • Surrounded by Idiots: Jessica's estimation of her situation in high school, and to a lesser degree in life at large. It's often hinted that it's not quite as bad as she thinks, though.
  • Their First Time: Jessica and Marcus has this at the end of the second book. We don't get any details, but Jessica says it was about as good as could be expected.
  • The Unfavorite: Jessica, compared to her picture-perfect sister Bethany.
  • Unreliable Narrator: Jessica ends up being wrong about a lot of things, especially due to failing to notice other people's Character Development.
  • Unlucky Childhood Friend: Scotty.
  • Verbal Tic: Sara can't go two sentences without using the terms "omigod!" or "quote-unquote." Or both.
    • Len speaks in fragmented sentences with a lot of "uhm"s and "er"s.
    • Bethany tends to change her way of speaking to whatever she thinks is cool at the moment, like adopting a faux-French accent while visiting France.
  • World Half Full: What Jessica tends to conclude in her more peaceful moments. No one's perfect, nothing quite lives up to the hype, the world only rarely makes sense and all good things eventually end. But at the same time, most people aren't as bad as they might seem either, your family and friends will love you as well as they can, and there's still a lot of joy to be found in life while it lasts.
  • You Are Better Than You Think You Are: Jess gets an unintentional one when someone writes a book very thinly based on Jessica and her friends. The characters based on her friends are all portrayed as pathetic idiots, while "Jenn Sweet" is described practically in glowing terms. The best Jess can figure is that the author made the character out to be what Jess herself could be if she wasn't such a screwup, but when she actually meets the author again and asks about it, the author is just confused - the Jenn Sweet character is based exactly on how she saw Jessica, as someone who was a lot more awesome than she was aware of.