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* NumberedSequels: Each booh in both the main series and the prequel series incorporates its number in the title.

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* NumberedSequels: Each booh book in both the main series and the prequel series incorporates its number in the title.
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* AmbiguousDisorder: Hyper-aware of details but frequently blindsided by unexpected developments, poor social skills but high intelligence, deeply introverted, prone to over-thinking and depression... it's easy to get the impression that Jessica is mildly autistic.
* AttentionDeficitOhShiny: Marcus gets formally diagnosed with Attention Deficiency Disorder in ''Sloppy Firsts'', though he personally thinks that that's just a label people like to slap on those who don't conform.
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* NumberedSequels: Each booh in both the main series and the prequel series incorporates its number in the title.

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** 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.



--->This wasn't [[EmbarrassingNickname Pepe le Pew]]. It was Pepe le Puberty.

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--->This wasn't [[EmbarrassingNickname Pepe le Pew]]. It This was Pepe le Puberty.



* 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.



* VerbalTic: [[ValleyGirl Sara]] can't go two sentences without using the terms "omigod!" or "quote-unquote." Or both.

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* VerbalTic: VerbalTic:
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[[ValleyGirl Sara]] can't go two sentences without using the terms "omigod!" or "quote-unquote." Or both.



** 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.
** Mac goes "tch" a lot, typically when he feels that Jessica has said something unusually stupid.

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** 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.
** Mac
[[CoolTeacher Mac]] goes "tch" a lot, typically when he feels that Jessica has said something unusually stupid.
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* StatuesqueStunner: Hope is six foot tall, which along with her bright red hair gives her a very striking appearance.
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* RomanticTwoGirlFriendship: Jess and Hope were ''extremely'' close, to the point where Hope moving away throws Jess into a year-long depression. Despite that, Jess is surprised and annoyed that anyone [[MistakenForGay would think]] that she's a [[UnusualEuphemism "vagitarian."]]

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* BrainlessBeauty: Jessica's estimation of Bridget in the first book, though she eventually has to admit that Bridget is smarter than she seems. Bethany is a straighter example, since she seems to actively go out of her way to avoid having to think.



* FunWithAcronyms: The summer writing class Jessica attends in ''Second Helpings'' is called SPECIAL (Summer Pre-College Enrichment Curriculum in Artistic Learning).



* HotForTeacher: By her own admission (and to her embarrassment, [[spoiler: especially when he finds out about it]]), Jessica for Mac when attending SPECIAL.
* ImAManICantHelpIt: While she admits that it feeds into the "promiscous man = stud, promiscous woman = slut" DoubleStandard, Jessica actually believes this, to a point. That doesn't mean she ''likes'' seeing guys sleeping around, mind, only that she's not ''surprised.''



* LikeFatherLikeDaughter: Jessica's mom claims this about Jessica and her dad.
-->'''Mom:''' You're both [[ThePerfectionist perfectionists.]] You're both hardheaded. You both [[NoSocialSkills have trouble dealing with people]]. You both get depressed when things don't go your way. You both think too much. You both keep your feelings inside, then [[RantInducingSlight explode at inopportune moments.]]



* NiceGirl: While she can be a bit thoughtless at times, Bridget is probably the sweetest character in the books.



* RetCon: In ''Sloppy Firsts'' Jessica claims that the events of the book marks the first time Marcus has ever said more than two words to her. The prequel series shows them not only interacting quite a lot, but actually developing much the same dynamic (him being bizarre and obnoxious, her being alternately annoyed and fascinated) as they have in ''Sloppy Firsts'' back when they were in junior high.

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* RetCon: In ''Sloppy Firsts'' Jessica claims that the events of the book marks the first time she and Marcus has have ever said more than two words talked to her. each other. The prequel series shows them that they not only interacting quite a lot, lot back when they were in junior high, but actually developing developed much the same dynamic (him being bizarre and obnoxious, her being alternately annoyed and fascinated) as they have in ''Sloppy Firsts'' back when they were in junior high.Firsts''.


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** Mac goes "tch" a lot, typically when he feels that Jessica has said something unusually stupid.
* WeUsedToBeFriends: Jess and Bridget, in the first book. They grow closer again over the course of the series.
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* ImmediateSequel: In contrast with the main series, where months or years go by between installments, the prequel novels follow each other seamlessly as well as just generally having a much compressed time frame (all three of them take place during the first semester of Jessica's first year in junior high). [[LampshadeHanging Lampshaded]] at one point when Jessica says that it feels like the events of the last book was ''ages'' ago and her grandmother tells her that that's because time seems to go by very slowly when you're twelve years old.

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* ImmediateSequel: In contrast with the main series, where months or years go by between installments, the prequel novels follow each other seamlessly as well as just generally having a much compressed time frame (all three of them take place during the first semester of Jessica's first year in junior high). [[LampshadeHanging Lampshaded]] at one point when Jessica says that it feels like the events of the last book was ''ages'' ago and her grandmother tells her that that's because [[TimeDissonance time seems to go by very slowly when you're twelve years old.]]

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* OnceASeason: Each of the first three books ends with Jessica and Hope meeting up.

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* OnceASeason: OnceASeason:
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Each of the first three books ends with Jessica and Hope meeting up.up.
** Each of the prequels starts with Bethany giving Jessica an "[=IT=] List" that she claims will help her with her current source of angst.
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* HarsherInHindsight: InUniverse. Jessica recalls Hope's brother Heath making her laugh by pretending to snort powdered sugar like cocaine, and how that memory turned a lot less funny after he died from a drug overdose six months later.
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* StrawFeminist: Manda tends to justify her questionable behaviour with feminist rhetoric, to Jessica's disgust. Jessica also considers herself a feminist, mind you, but in a more rudimentary girls-are-worth-as-much-as-boys way that doesn't use as much dogma and name-dropping.

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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]], is not amused. She also hates being called "Jessie," preferring either "Jess" or "Jessica."

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* EmbarrassingNickname: 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]], is not amused. She also hates being called "Jessie," preferring either "Jess" or "Jessica."" Even worse is the name she finds out that people are calling her behind her back in seventh grade - "the Woodchick," because she's [[TheSmurfettePrinciple the only girl taking woodshop class]] and also [[ACupAngst flat as a board.]]



* TheNicknamer: Jessica is fond of coming up with sarcastic nicknames for people, though she rarely calls people by them to their faces but sticks to using them in her journal.

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* TheNicknamer: TheNicknamer:
**
Jessica is fond of coming up with sarcastic nicknames for people, though she rarely calls people by them to their faces but sticks to using them in her journal.journal.
** Mr. Pudel, Jessica's seventh grade woodshop teacher, claims to have [[AmbiguousDisorder a condition that prevents him from learning people's names]] and therefore assigns his students nicknames, most of them embarrassing. Jessica gets off relatively easy by being called "Clementine" (as in, "oh my darling...").
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* TheObiWannabe: Bethany in the prequel series would like to think that she's a CoolBigSis dispensing sage advice for how to succeed in junior high. The problem is, the item on her "[=IT=] Lists" are not only of questionable value, but are also written as [[IceCreamKoan cutesy one-liners]] that could ''really'' use some explanation for what they're supposed to mean. Jessica actually [[GenreSavvy figures that out]] by the end of the first book, but she still decides to continue going along with the lists, because at least they make her life interesting.

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* TheObiWannabe: Bethany in the prequel series would like to think that she's a CoolBigSis dispensing sage advice for how to succeed in junior high. The problem is, the item items on her "[=IT=] Lists" are not only of questionable value, but are also written as [[IceCreamKoan cutesy one-liners]] that could ''really'' use some explanation for what they're supposed to mean. Jessica actually [[GenreSavvy figures that out]] by the end of the first book, but she still decides to continue going along with the lists, because at least they make her life interesting.
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[=McCafferty=] has also written three prequel novels, dealing with Jessica's earlier teenage years:

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[=McCafferty=] has also written three prequel novels, dealing with Jessica's earlier teenage years:
first year in junior high:
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* ImmediateSequel: In contrast with the main series, where months or years go by between installments, the prequel novels follow each other seamlessly as well as just generally having a much compressed time frame (all three of them take place during the first semester of Jessica's first year in junior high). [[LampshadeHanging Lampshaded]] at one point when Jessica says that it feels like the events of the last book was ''ages'' ago and her grandmother tells her that that's because time seems to go by very slowly when you're twelve years old.
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* AccidentalAthlete: Sort of - Jess becomes and Accidental ''School Mascot'' by messing up her cheerleader tryouts. It turns out that [[SlapstickKnowsNoGender she's got a rare knack for looking hilarious while falling on her face.]] Later played more straight as she gets recruited to the track team when the coach sees how much speed she can pick up while [[ItMakesSenseInContext fleeing from a lovesick goose wearing a fifty-pound seagull costume.]]

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* AccidentalAthlete: Sort of - Jess becomes and an Accidental ''School Mascot'' ''School'' ''{{Mascot}}'' by messing up her cheerleader tryouts. It turns out that [[SlapstickKnowsNoGender she's got a rare knack for looking hilarious while falling on her face.]] Later played more straight as she gets recruited to the track team when the coach sees how much speed she can pick up while [[ItMakesSenseInContext fleeing from a lovesick goose wearing a fifty-pound seagull costume.]]
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* AccidentalAthlete: Sort of - Jess becomes and Accidental ''School Mascot'' by messing up her cheerleader tryouts. It turns out that [[SlapstickKnowsNoGender she's got a rare knack for looking hilarious while falling on her face.]] Later played more straight as she gets recruited to the track team when the coach sees how much speed she can pick up while [[ItMakesSenseInContext fleeing from a lovesick goose wearing a fifty-pound seagull costume.]]
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* RetCon: In ''Sloppy Firsts'' Jessica claims that the events of the book marks the first time Marcus has ever said more than two words to her. The prequel series shows them not only interacting quite a lot, but actually developing much the same dynamic (him being bizarre and obnoxious, her being alternately annoyed and fascinated) as they have in ''Sloppy Firsts'' back when they were in junior high.
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* TheObiWannabe: Bethany in the prequel series would like to think that she's a CoolBigSis dispensing sage advice for how to succeed in junior high. The problem is, the item on her "[=IT=] Lists" are not only of questionable value, but are also written as [[IceCreamKoan cutesy one-liners]] that could ''really'' use some explanation for what they're supposed to mean. Jessica actually [[GenreSavvy figures that out]] by the end of the first book, but she still decides to continue going along with the lists, because at least they make her life interesting.
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* LighterAndSofter: The prequel series. While Jessica is still [[TheEeyore miserable most of the time]], since she's a lot younger there than in the main books, the problems she faces are less weighty and serious.


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* MeaningfulName: Hope. The reason why Jessica is so depressed for the entire first book is because she has ''lost Hope.''

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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.

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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.book, and later to a number of other characters. 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.



* {{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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* {{Adorkable}}: Jess claims to prefer guys who are "geeky-cute." Her actual dating track record [[UnreliableNarrator casts some]] [[SlapSlapKiss doubt on]] [[AllGirlsWantBadBoys that, though.]]]] Len fits this trope to a T, but when he and Jessica are dating she's constantly bored out of her skull because he's too much of a goodie-two-shoes NiceGuy to provide the sort of [[SnarkToSnarkCombat intellectual challenge]] that she actually seems to want from a guy.



* LadykillerInLove: Marcus, who [[spoiler: starts out trying to seduce Jessica basically as a self-imposed challenge, but then falls in love with her for real.]]



* TheNicknamer: Jessica is fond of coming up with sarcastic nicknames for people, though she rarely calls people by them to their faces but sticks to using them in her journal.



* OldShame: [[spoiler: Hy]] ends up feeling this way about her book about Jessica and her friends, and is grateful when the movie version ends up in DevelopmentHell.

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* OldShame: InUniverse. [[spoiler: Hy]] ends up feeling this way about her book about Jessica and her friends, and is grateful when the movie version ends up in DevelopmentHell.
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A Man Is Not A Virgin is no longer a trope.


** 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]]) [[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]]



* 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,]] 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,]] and [[AManIsNotAVirgin getting laid is the one thing a guy must do.]] do. Jessica is less than sympathetic.
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* OldShame: [[spoiler: Hy]] ends up feeling this way about her book about Jessica and her friends, and is grateful when the movie version ends up in DevelopmentHell.
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* SlapSlapKiss: 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.

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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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* HesAllGrownUp: HesAllGrownUp:
** 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 PrecociousCrush on her.
--->This wasn't [[EmbarrassingNickname 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 [[{{Nerd}} his personality]] remaining the same, though.
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* HighSchool: The setting for the first two novels, which as usual for the trope treat the high school drama as SeriousBusiness. 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.

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* HighSchool: The setting for the first two novels, novels and the prequels, which as usual for the trope treat the high school drama as SeriousBusiness. 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.
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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 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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* GoodBadGirl: 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 one of Jessica's college friends, friend Dexy [[spoiler: 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 [[AllWomenAreLustful girls]] ''or'' [[ImAManICantHelpIt guys]] who she sees as oversexed.
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* 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 and even more so when it happens again in the third - because she's sexually active at the time, and at first she's [[PregnancyScare terrified that she's pregnant.]]

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* NoPeriodsPeriod: Averted, Jessica's period gets mentioned on occasion, though mostly for its absence - apparently 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 [[PregnancyScare terrified that she's pregnant.]]

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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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* GoodGirlsAvoidAbortion: Averted. When Jessica [[PregnancyScare briefly worries that she's pregnant in book three, 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.



* 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 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.

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* 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 and even more so when it happens again in the third - because she's sexually active at the time, and at first she's [[PregnancyScare terrified that she's pregnant.]]


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* PregnancyScare: Jess has one in book three, though it takes place between chapters and is told in retrospect.
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* 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.]]

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* 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.]]

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