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* TheMatchmaker: 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.
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* SexIsEvil: 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. [[spoiler: In the third book, he turns out to have lost this along with his other youthful certainties, and Jessica ends up taking his virginity.]]
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* GoodGirlsAvoidAbortion: 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.
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* ChildrenRaiseYou: Bethany actually [[CharacterDevelopment matures slightly]] after having a daughter. ''Slightly,'' mind you.
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* ItsAllAboutMe: Bethany starts out this way, until she [[ChildrenRaiseYou has a baby and broadens her horizons a little.]] At which point she promptly turns around and [[{{Hypocrite}} accuses Jessica of being this way.]]
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* VerbalTic: [[ValleyGirl Sara]] can't go two sentences without using the terms "omigod!" or "quote-unquote." Or both.
** [[{{Nerd}} 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.
** [[{{Nerd}} 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.
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* HesAllGrownUp: 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 [[{{Nerd}} his personality]] remaining the same, though.
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* {{Adorkable}}: Jess claims to prefer guys who are "geeky-cute." Her actual dating track record [[UnreliableNarrator casts some]] [[SlapSlapKiss doubt on]] [[AllGirlsWantBadBoys that, though.]]
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* DoYouWantToCopulate: 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 [[{{Adorkable}} other reasons.]]
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** 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]]It refers to him getting plenty of [[UnusualEuphemism donuts]] while at the same time being constantly [[TheStoner baked.]][[/note]]
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** 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 [[AManIsNotAVirgin compliment of sorts) sorts]]) [[note]]It refers to him getting plenty of [[UnusualEuphemism donuts]] while at the same time being constantly [[TheStoner baked.]][[/note]]
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* WorldHalfFull: 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.
* YouAreBetterThanYouThinkYouAre: 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.
* YouAreBetterThanYouThinkYouAre: 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.
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* WorldHalfFull: 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 [[HiddenDepths aren't as bad as they might seem 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.
* YouAreBetterThanYouThinkYouAre: 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 [[TheAce glowingterms.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.
* YouAreBetterThanYouThinkYouAre: 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 [[TheAce glowing
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* DCupDistress: Manda claims to hate her well-developed bust. [[ACupAngst Jess]] grumpily notes that that doesn't stop her from always wearing borderline-{{Stripperific}} clothes that [[BigBreastPride show it off to best advantage.]]
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* YouAreBetterThanYouThinkYouAre: 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.
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* YouAreBetterThanYouThinkYouAre: 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.of.
----
----
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* WorldHalfFull: 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.
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* WorldHalfFull: 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.lasts.
* YouAreBetterThanYouThinkYouAre: 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.
* YouAreBetterThanYouThinkYouAre: 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.
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* EmbarrassingNickname: 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."
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* EmbarrassingNickname: 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, [[IResembleThatRemark possibly proving his point, point]], is not amused. She also hates being called "Jessie," preferring either "Jess" or "Jessica."
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* JerkJock: 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 [[AManIsNotAVirgin getting laid is the one thing a guy must do.]] Jessica is less than sympathetic.
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* JerkJock: Scotty turns into one in the second book. At one point, he claims that he doesn't actually want to be one, but [[AllGirlsWantBadBoys it's the only way to get laid, laid,]] and [[AManIsNotAVirgin getting laid is the one thing a guy must do.]] Jessica is less than sympathetic.
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* RealityEnsues: 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 [[IvyLeagueForEveryone anyone who didn't go to Harvard has failed at life]], she [[RantInducingSlight 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 [[FirstWorldProblems 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 LifeIsntFair. Then, right at the heels of that, the chapter ends with:
-->I got fired, of course.
-->I got fired, of course.
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* BiggerIsBetterInBed: Jessica's opinion, as expressed in the second book, is that while she isn't sure if it's ''better'' per se, it doesn't hurt.
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* BiggerIsBetterInBed: Jessica's opinion, as expressed in the second third book, is that while she isn't sure if it's ''better'' per se, it sure doesn't hurt.
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* HappyEndingOverride: The main theme of the third book. The second book ends with Jess finally graduating from the [[HighSchoolIsHell high school she thought was hell]], about to leave the small town where she felt SurroundedByIdiots in to go to the big city and attend the college of her dreams, and in a relationship with a guy she's crazy about. Then RealityEnsues 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.
* HighSchool: The setting for the first two novels, which as usual for the trope treat the high school drama as SeriousBusiness. Much of the third is devoted to Jessica being astonished at how little it all turned out to mean once she got out into the real world.
* HighSchool: The setting for the first two novels, which as usual for the trope treat the high school drama as SeriousBusiness. Much of the third is devoted to Jessica being astonished at how little it all turned out to mean once she got out into the real world.
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* HappyEndingOverride: The main theme of the third book. The second book ends with Jess finally graduating from the [[HighSchoolIsHell high school she thought was hell]], about to leave the small town where she felt SurroundedByIdiots in to go move to the big city and attend the college of her dreams, and in a relationship with a guy she's crazy about. Then RealityEnsues 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.
* HighSchool: The setting for the first two novels, which as usual for the trope treat the high school drama as SeriousBusiness.Much of That part is subverted in the third 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.
* HighSchool: The setting for the first two novels, which as usual for the trope treat the high school drama as SeriousBusiness.
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* HappyEndingOverride: The main theme of the third book. The second book ends with Jess finally graduating from the high school where she felt SurroundedByIdiots, about to leave the small town she felt stifled in to go to the big city and attend the college of her dreams, and in a relationship with a guy she's crazy about. Then RealityEnsues and life after high school turns out to be even harder and more confusing, just in other days. 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.
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* HappyEndingOverride: The main theme of the third book. The second book ends with Jess finally graduating from the [[HighSchoolIsHell high school where she felt SurroundedByIdiots, thought was hell]], about to leave the small town where she felt stifled SurroundedByIdiots in to go to the big city and attend the college of her dreams, and in a relationship with a guy she's crazy about. Then RealityEnsues and life after high school turns out to be even harder and more confusing, just in other days. 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.on.
* HighSchool: The setting for the first two novels, which as usual for the trope treat the high school drama as SeriousBusiness. Much of the third is devoted to Jessica being astonished at how little it all turned out to mean once she got out into the real world.
* HighSchool: The setting for the first two novels, which as usual for the trope treat the high school drama as SeriousBusiness. Much of the third is devoted to Jessica being astonished at how little it all turned out to mean once she got out into the real world.
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* HappyEndingOverride: The main theme of the third book. The second book ends with Jess finally graduating from the high school where she felt SurroundedByIdiots, about to leave the small town she felt stifled in to go to the big city and attend the college of her dreams, and in a relationship with a guy she's crazy about. Then RealityEnsues and life after high school turns out to be even harder and more confusing, just in other days. 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.
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* SoapboxSadie: Paul joins a protest group made up entirely of these in college. As Jess puts it, they're so busy being angry about absolutely every single thing that's wrong with the world that she doubts they'll ever get around to actually doing anything about any particular one of them.
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* SoapboxSadie: Paul joins a protest group made up entirely of these in college. As Jess puts it, they're so busy being angry about is initially excited to meet them, but is quickly put off by their self-righteousness and the way they seem to be against absolutely every single thing that's wrong with the world that she doubts they'll ever get around to actually doing anything about any particular one of them.''everything.''
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* SoapboxSadie: Paul joins a protest group made up entirely of these in college. As Jess puts it, they're so busy being angry about absolutely every single thing that's wrong with the world that she doubts they'll ever get around to actually doing anything about any particular one of them.
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* ButIWouldReallyEnjoyIt: 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.
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* ButIWouldReallyEnjoyIt: 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.one:
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* ButIWouldReallyEnjoyIt: 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.
-->I want to. Oh, God, do I want to.
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** 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]]It refers to him getting plenty of [[UnusualEuphemism donuts]] while at the same time being constantly [[TheStoner baked.]][[/note]]
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** Sara, who is sensitive about her weight, does not enjoy being caled "Bruiser."
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** Sara, who is sensitive about her weight, does not enjoy being caled called "Bruiser."
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* DoggedNiceGuy: Scotty spends the first book being this.
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* DoggedNiceGuy: Scotty spends the first book being this. In the second book, he drops the Dogged part. [[TookALevelInJerkAss And sadly also the Nice Guy part.]]
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** Sara, who is sensitive about her weight, does not enjoy being caled "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.
** 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.
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* SuddenlySexuality: [[spoiler: Manda, supposedly. Jessica suspects that her sudden turn from [[ReallyGetsaround boy-crazy]] to lesbian is just the last version of Manda's habit of [[StrawFeminist using her sexuality to make a questionable political statement]].]]
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The ''Jessica Darling'' series of novels by Megan McCafferty are tragicomic slice-of-life stories chronicling the life of their [[TheSnarkKnight 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 [[ReformedRakes reformed bad boy]] Marcus Flutie.
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The ''Jessica Darling'' series of novels by Megan McCafferty [=McCafferty=] are tragicomic slice-of-life stories chronicling the life of their [[TheSnarkKnight 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 [[ReformedRakes reformed bad boy]] Marcus Flutie.
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McCaffferty has also written three prequel novels, dealing with Jessica's earlier teenage years:
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* IncompatibleOrientation: Happens to poor Jess more than once.
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* IncompatibleOrientation: Happens to poor Jess more than once.
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The Jessica Darling series of novels by Megan McCafferty, chronicling the life of their [[TheSnarkKnight smart, cynical and perpetually gloomy]] eponymous protagonist from her sixteenth birthday up to her late 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 [[ReformedRakes reformed bad boy]] Marcus Flutie.
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The Jessica Darling ''Jessica Darling'' series of novels by Megan McCafferty, McCafferty are tragicomic slice-of-life stories chronicling the life of their [[TheSnarkKnight smart, cynical and perpetually gloomy]] eponymous protagonist from her sixteenth birthday up to through her late twenties.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 [[ReformedRakes reformed bad boy]] Marcus Flutie.
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The Jessica Darling series of novels by Megan McCafferty, chronicling the life of their [[TheSnarkKnight smart, cynical and perpetually gloomy]] eponymous protagonist from her sixteenth birthday up to her late 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 (though hilarious) setbacks, and enjoys an on-again, off-again relationship with [[ReformedRakes reformed bad boy]] Marcus Flutie.
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The Jessica Darling series of novels by Megan McCafferty, chronicling the life of their [[TheSnarkKnight smart, cynical and perpetually gloomy]] eponymous protagonist from her sixteenth birthday up to her late 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 (though hilarious) setbacks, setbacks and lessons in humility, and enjoys an on-again, off-again relationship with [[ReformedRakes reformed bad boy]] Marcus Flutie.
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* GoodBadGirl: Manda ''thinks'' she is this and that her promiscuity is a sign of her refusal to bow to patriarchal sexual moores, but Jessica is definitely not convinced. Later played more straight with one of Jessica's college friends, but on the whole, Jessica doesn't think much of [[AllWomenAreLustful girls]] ''or'' [[ImAManICantHelpIt guys]] who she sees as oversexed.
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* GoodBadGirl: Manda ''thinks'' she is this and that her promiscuity is a sign of her refusal to bow to patriarchal sexual moores, norms, but Jessica is definitely not convinced. Later played more straight with one of Jessica's college friends, but on the whole, Jessica doesn't think much of [[AllWomenAreLustful girls]] ''or'' [[ImAManICantHelpIt guys]] who she sees as oversexed.
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* A-CupAngst: Jessica often bemoans her "A-minus cup" bust.
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* A-CupAngst: ACupAngst: Jessica often bemoans her "A-minus cup" bust.
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The Jessica Darling series of novels by Megan McCafferty, chronicling the life of their [[TheSnarkKnight smart, cynical and perpetually gloomy]] eponymous protagonist from her sixteenth birthday up to her late 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 (though hilarious) setbacks, and enjoys an on-again, off-again relationship with [[ReformedRakes 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 UnreliableNarrator, but also to a lot of Jessica's [[FirstPersonSnarker 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''
McCaffferty 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-CupAngst: Jessica often bemoans her "A-minus cup" bust.
* BigBeautifulWoman: 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.
* BiggerIsBetterInBed: Jessica's opinion, as expressed in the second book, is that while she isn't sure if it's ''better'' per se, it doesn't hurt.
* CharacterDevelopment: 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.
* CoolLoser: 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 ''[[TheEeyore felt]]'' pathetic and miserable.
* CoolOldLady: Jessica's grandmother believes in making the most of retirement home life.
* DoggedNiceGuy: Scotty spends the first book being this.
* TheEeyore: 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.
* EmbarrassingNickname: 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."
* EruditeStoner: Marcus, until he cleans up. Bridget claims that Jessica just generally tends to go for boys of the "stonah lovah" variety.
* FirstPersonSnarker: Jess, of course.
* GoodBadGirl: Manda ''thinks'' she is this and that her promiscuity is a sign of her refusal to bow to patriarchal sexual moores, but Jessica is definitely not convinced. Later played more straight with one of Jessica's college friends, but on the whole, Jessica doesn't think much of [[AllWomenAreLustful girls]] ''or'' [[ImAManICantHelpIt guys]] who she sees as oversexed.
* JerkJock: 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 [[AManIsNotAVirgin getting laid is the one thing a guy must do.]] Jessica is less than sympathetic.
* IncompatibleOrientation: Happens to poor Jess more than once.
* ManlyGay: [[spoiler: Paul]], as it turns out.
* NoPeriodsPeriod: 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 [[spoiler: 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.]]
* OnceASeason: Each of the first three books ends with Jessica and Hope meeting up.
* ParentsAsPeople: Jessica's parents are far from perfect, but they try.
* TheSnarkKnight: Jessica.
* SurroundedByIdiots: 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 [[WorldHalfFull not quite as bad]] [[UnreliableNarrator as she thinks]], though.
* TheirFirstTime: Jessica and [[spoiler: 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.
* TheUnfavorite: Jessica, compared to her picture-perfect sister Bethany.
* UnreliableNarrator: Jessica ends up being wrong about a lot of things, especially due to failing to notice other people's CharacterDevelopment.
* UnluckyChildhoodFriend: Scotty.
* WorldHalfFull: 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.
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 UnreliableNarrator, but also to a lot of Jessica's [[FirstPersonSnarker 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''
McCaffferty 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''
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!!Provides Examples Of:
* A-CupAngst: Jessica often bemoans her "A-minus cup" bust.
* BigBeautifulWoman: 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.
* BiggerIsBetterInBed: Jessica's opinion, as expressed in the second book, is that while she isn't sure if it's ''better'' per se, it doesn't hurt.
* CharacterDevelopment: 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.
* CoolLoser: 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 ''[[TheEeyore felt]]'' pathetic and miserable.
* CoolOldLady: Jessica's grandmother believes in making the most of retirement home life.
* DoggedNiceGuy: Scotty spends the first book being this.
* TheEeyore: 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.
* EmbarrassingNickname: 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."
* EruditeStoner: Marcus, until he cleans up. Bridget claims that Jessica just generally tends to go for boys of the "stonah lovah" variety.
* FirstPersonSnarker: Jess, of course.
* GoodBadGirl: Manda ''thinks'' she is this and that her promiscuity is a sign of her refusal to bow to patriarchal sexual moores, but Jessica is definitely not convinced. Later played more straight with one of Jessica's college friends, but on the whole, Jessica doesn't think much of [[AllWomenAreLustful girls]] ''or'' [[ImAManICantHelpIt guys]] who she sees as oversexed.
* JerkJock: 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 [[AManIsNotAVirgin getting laid is the one thing a guy must do.]] Jessica is less than sympathetic.
* IncompatibleOrientation: Happens to poor Jess more than once.
* ManlyGay: [[spoiler: Paul]], as it turns out.
* NoPeriodsPeriod: 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 [[spoiler: 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.]]
* OnceASeason: Each of the first three books ends with Jessica and Hope meeting up.
* ParentsAsPeople: Jessica's parents are far from perfect, but they try.
* TheSnarkKnight: Jessica.
* SurroundedByIdiots: 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 [[WorldHalfFull not quite as bad]] [[UnreliableNarrator as she thinks]], though.
* TheirFirstTime: Jessica and [[spoiler: 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.
* TheUnfavorite: Jessica, compared to her picture-perfect sister Bethany.
* UnreliableNarrator: Jessica ends up being wrong about a lot of things, especially due to failing to notice other people's CharacterDevelopment.
* UnluckyChildhoodFriend: Scotty.
* WorldHalfFull: 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.
