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  • Alternate Character Interpretation:
    • The members of the eponymous club often come off as cult-like. Every single time one of them dares to hang out with a new friendnote , wear a different hairstyle, or do something else that bothers them, the rest of the sitters all have a collective Freak Out and/or treat the offending sitter coldly until she apologizes for whatever it was she did wrong. Mercilessly mocked in this Robot Chicken sketch, where Abby refuses to join the club and they respond by stealing her boyfriend, siccing a wolf on her, gunning down her parents, and burning down her house.
    • Every single time Jenny Prezzioso is mentioned, the sitters say something negative about her. To be fair, Jenny is bratty, but it is mostly due to her young age (four) as well as the way she has been raised by her mother. This is why some fans feel that she is not as bad as the sitters think, and is instead just a fairly stubborn girl who hates getting dirty. It doesn't help either that the sitters seem to have difficulty separating the aspects that are just unusual for a kid (like her dislike of getting dirty) from her genuine bad behavior (like throwing tantrums or being mean to other kids), which ends up making even the legitimate complaints seem petty.
    • Some fans feel that Claudia and Mean Janine should have been called Claudia Acts Bratty to Janine or Janine and Mean Claudia.
    • Patrick Thomas is generally regarded as a Jerkass by the fandom (and not without reason, all things considered), but one aspect of this may have a subconscious explanation. When he gets remarried in Kristy's Big News, Kristy and her stepmother-to-be have a heart-to-heart the night before the wedding, and Kristy finally explains to this very nice woman just why she and her brothers are so unhappy with their father. Her stepmother-to-be replies that this doesn't come as a complete surprise. Apparently, Patrick talked a lot about his kids throughout their courtship, but the ages of the kids in his stories clued her in to the fact that he's had no relationship with them since he left their mother. David Michael was a baby at the time, so he barely featured anywhere in his father's stories. It could be extrapolated that Patrick basically acts like David Michael doesn't exist in order to shrug off the guilt he feels for abandoning his kids and never even knowing his youngest at all.
    • Richard Spier is portrayed as a strict parent throughout the series, but really, apart from the first four books, some readers would say he isn't so strict compared to their own parents (especially readers from backgrounds where stern, even authoritarian, parenting is the norm). This is likely due in large part to the way the character was established at the start of the series, when he did such things as forbidding Mary Anne to go the pizza party because he doesn't want her to "waste" a few dollars on pizza, dictating how she dresses and does her hair, or not letting her talk on the phone after dinner unless it's about homework; even though he experienced some Character Development pretty early in the books, readers were left with the impression of him as stern and controlling. The way he's indicated to relax more later in the series, especially once he rekindles his relationship with his old flame Sharon, may have been written to counterbalance this first impression.
    • After the divorce, does Stacey's father take her out to a lot of places because he misses her, wants to lord it over her mother, or because he's worried about her health and wants her to have as many things to enjoy in life while she can?
  • Archive Panic: It has 131 main books, 15 super specials, 122 spin off series (12 books that spun off from that series), 36 mystery books (4 super mysteries), and yet another spin off series with 15 books. That’s about 300 books of reading material and would take up about 4 shelves of books if you want to display them all.
  • Creator's Pet: Kristy's stepsister, Karen, is usually loved by other characters (except when she goes too far, such as in Kristy's Big Day), but disliked by many fans for being too annoying and overused, as she is one of the kids who appears more frequently in almost every book; she's also the main character of a spinoff called Baby-Sitter's Little Sister.
  • Designated Villain:
    • Janine is demonized by Claudia for bragging a bit, but this is mostly because she has an IQ of 196. This is especially prominent in Claudia and Mean Janine, where she's supposed to be Claudia's antagonist, but Janine doesn't do anything wrong in the book outside of being unintentionally condescending at times.
    • Cokie Mason earns her villain status more often than not, but becomes this for the whole BSC on a few occasions. Partially Justified by her history with them, since it's understandable that the club's perception of her would be influenced by past experience, even if she's not doing anything bad at that particular moment.
    • Pamela Harding in the Little Sister spin-off series is meant to be a prepubescent Alpha Bitch, but ends up coming across as this. While she does have some genuinely snotty moments, the primary reason for her demonization was that at Karen's sleepover party, Pamela didn't want to eat pizza, didn't like The Wizard of Oz, and preferred sleeping in a bed to sleeping on the floor.
  • Diagnosed by the Audience:
    • Alexis, Mallory's initial roommate when she goes to boarding school, clearly has some kind of disorder that leads her to behave in very unpredictable ways.
    • The extent of Claudia's difficulties with school, particularly post-Flanderization, would seem to indicate some kind of learning disability or something else along those lines.
    • A character in Super Mystery #3, a sixth-grader called Eileen, is described as a "social klutz". Likely unintentional, but many of her traits are in line with the level of autism that often goes undiagnosed. She is bullied heavily, and it is noted that she either makes no eye contact or does it too intensely; Mallory also notes that she often speaks up in class, but is quieter on the trip because of the bullying.
  • Ensemble Dark Horse:
    • Shannon is very popular among members of some snark communities. Amusingly, so is background character Pete Black. Janine also has a following.
    • Logan is also rather popular; he even got two "Reader's Request" books narrated by him.
    • Mimi, for being very endearing in general and for being understanding of Claudia.
  • Fan Nickname: "K. Ron" (after L. Ron Hubbard) for Kristy and "BSCult" have become popular on some snark communities.
  • Fanon:
    • Hormone-Addled Teenager Stacey tends to get depicted as bisexual in fan works. Dawn and Claudia are also frequently depicted as bi.
    • Claudia will go to art school (usually in New York City).
    • The tomboyish Kristy is either lesbian or bisexual.
    • Given her in-universe lack of interest in boys or dating, Abby is either gay or asexual.
    • The characters all marry their middle school sweethearts. At minimum, Logan and Mary Anne end up together.
    • Byron, the most sensitive of the Pike triplets, is gay.
    • Stacey Really Gets Around in works set post-series.
    • The Ambiguously Gay Ducky is gay. To be fair, this is heavily implied.
  • Fandom Nod: In the later books, Claudia's terrible spelling is a handy way to figure out how to pronounce some of the more unusual names. She spells "Spier" "S-P-E-E-R" and "Myriah" "M-A-R-I-A," for example.
  • Harsher in Hindsight:
    • In the series finale, the girls make a time capsule to be opened in seven years and each contribute a letter. In Dawn's letter, she talks about flying between California and Connecticut and remarks that maybe by the time the capsule is opened, air travel will have changed somehow. The book was published in 2000.
    • In Mary Anne and the Library Mystery, Mary Anne starts having nightmares about fires burning out of control in response to the fires at the library. In the last book of the main series, her house burns down.
    • In Mallory Hates Boys (and Gym), Mallory humiliates herself playing volleyball in gym class. She vows not to cry, because if she does she will "never be able to show (her) face at SMS again" and "will have to change schools". Toward the end of the main series, Mallory becomes the target of such relentless bullying by her classmates that she winds up leaving SMS for an all-girls boarding school in Massachusetts.
  • He Also Did: David Levithan was introduced to Scholastic and got his start in writing by ghostwriting for this series.
  • Hilarious in Hindsight:
    • In Stacey's Ex-Best Friend, Laine asks if the girls are still gonna be baby sitting in the summer and asks if they ever considered getting paycheck jobs (despite the fact that they're thirteen) and mentioning that she got a real job — running the cash register at a nearby boutique. She brags that hundreds of people applied for the job and she was chosen. Her age not withstanding (she may have just turned fourteen), who would pick a young teenager for a job over possible high school and college kids, or young adults?! And did we mention that she already knows about this summer job and the book takes place in February?!
    • One subplot involves Marilyn and Carolyn Arnold sneaking a look at a horror movie and getting freaked out of their minds by it, to the point where they sleep in the same room with all the lights on, tape up electrical sockets, and set up traps for "ghosts," until they watch a documentary on how the movie was made. They become riveted by the special effects and demonstrations and declare it the coolest thing they've ever seen. Not only does it lift their fears, it makes them into horror movie fans, and they decide they want to direct their own horror movies when they grow up. Hmmm... that sounds a lot like the biography of a pair of Canadian twin sisters who are not only horror movie directors themselves, but host their own horror-themed game show, Hellevator!
    • Charlotte Johanssen's name is pretty amusing, considering the later popularity of Scarlett Johansson.
    • Bratty Half-Pint Karen Brewer is this after the "Karen" meme came out in the 2010s which focused on demanding, middle-aged, Caucasian women of privilege demanding to see the manager over some slight.
  • Hollywood Homely: If the descriptions of Janine are to be believed, we get a picture of a homely, awkward young woman with an unfortunate fashion sense. This makes sense for the early cover of Claudia and Mean Janine — but later, when the cover artist was replaced, Janine started looking more grown up and sexy with well-tailored clothing. She almost shows up her "prettier" younger sister!
  • Informed Wrongness:
    • Mary Anne decides that she wants to get a drastic new haircut, and asks the other members of the BSC if they think she would look good with a short hairstyle. They all tell her no, and are horrified when Mary Anne goes ahead and gets her hair cut. Dawn almost has a mental breakdown because Mary Anne dared to go have a father-daughter day at the mall, where she got her haircut and a new wardrobe to go with it, and the rest of the Club ignore her until she's the one to break down and apologise for not thinking of their feelings.
    • In Baby Sitters' Island Adventure Kristy is accused of overreacting by her boyfriend Bart after canceling a game after two of the babysitters and their charges (her friends and members of her team) have gotten shipwrecked on an island after a storm. He apologizes but still says she exaggerates, and she admits to "crying wolf".
    • Jessi's Aunt Cecilia (similar to how Richard Spier is regarded) is considered too strict and conservative regarding her supervision of her nieces and nephew, finding Jessi's parents to be crazy because they left Jessi in charge of her younger brother and sister for a weekend... the same eleven-year-old daughter they claim is too young to wear leggings, pierce her ears, or babysit other kids in the evening. (Although she is wrong to essentially blame Jessi, rather than her parents, for it—and she later admits that she was wrong and it was because she was upset about the situation and felt she had to blame someone available, which just happened to be Jessi.)
  • Jerkass Woobie: Karen is bratty, but given what she has had to deal with, her behavior is understandable. Her parents are divorced, and both remarried within a fairly short time frame. Even worse, Karen was apparently expected to adjust immediately despite being only six years old (later seven). The first time Kristy babysits her, Karen admits that she is supposed to avoid discussing the divorce because it upsets her little brother (who starts crying in the middle of the conversation), which leaves her with nowhere to vent her own feelings about the matter — and Karen takes on a kind of protective role towards Andrew, so she's probably managing his feelings on top of her own. In the earlier books at least, she spends only two weekends out of every month with her father, and he still insists on leaving her with a sitter for at least part of that time, and then Watson and Elizabeth adopt a baby which makes her feel a bit like her father is replacing her. (She eventually comes to accept Emily's place in the family.) Then, late into the series, after her parents have adjusted their custody arrangements so that she spends every other month with her father, her stepfather has to transfer to Chicago for six months — which involves moving the entire family, Karen and her brother included. But (much like Jeff and Dawn) Karen is so homesick that she can't make the adjustment and ends up going back to Stoneybrook to live with her father's family while Andrew stays with their mother's, meaning now she's separated (albeit temporarily) from the one member of her family with whom she always consistently lived and feeling guilty that she broke her promise to stay with him. Also, while her parents are on relatively amicable terms, they still occasionally have conflicts about how exactly they break down time with their kids (like when both families want the kids to be with them on Thanksgiving Day), with Karen and Andrew then ending up in the middle of said conflicts.
    • Also, as described in Karen Two-Two, Karen's vision issues require her to have two separate pairs of glasses, one for "regular" wear (presumably meaning distance) and another for reading. It's somewhat surprising that such a major vision issue wasn't diagnosed at an earlier age, and it can't be as easy for her as the book suggests. (In the graphic novels, she only has the one pair of glasses.)
  • LGBT Fanbase: A number of readers would later come out to be LGBT (if they hadn't already), since the main cast comprises close female friends with varying personalities. A large number of fanfics ship the girls with each other and there is much speculation and headcanoning over who is lesbian or bisexual, with Kristy, Mary Anne, Claudia, and Stacey being the girls most frequently depicted as queer. Helped by Ann M. Martin eventually coming out as queer in 2016.
  • Memetic Hair: Mary Anne ditches her braided pigtails four books in, but fans who start from the beginning of the series always remember her as having pigtails. Fans who started the series later or who were introduced to it by the 1995 movie, on the other hand, will always remember her as having short hair and view the pigtails as Early-Installment Weirdness.
  • Memetic Loser: Poor Mallory. She's the oldest of a large family, describes herself as unpretty with glasses and curly red hair, and thinks she's a baby who doesn't get to look as or dress as cool as the other members. Her father loses his job at one point, she gets mono, and she gets picked on in school all the time. Eventually she becomes so miserable at school that she gets herself into a boarding school and leaves the club (and the series) altogether.
  • Memetic Psychopath:
    • Kristy's bossy behavior is frequently exaggerated, especially by people who dislike the series.
    • Karen Brewer becomes a bratty hellion in fan-works.
  • Memetic Molester: Some snark blogs enjoy painting the BSC as girls who love children for all the wrong reasons, due to how odd and even creepy their obsession with them can come across to modern readers.
  • Memetic Mutation: The books often mention that Jessi is black and that she's the only black girl in the whole of the sixth grade — and not many other black people outside of her family are mentioned at all. Fans have exaggerated this.
  • Mis-blamed:
    • In-universe, Dawn and the Impossible Three has the BSC blame the Barrett children for their jobs being chaotic, and even has the Tag Line refer to them as monsters. The kids, however, are actually well-behaved for the most part, considering their parents are going through a very acrimonious divorce. The real problem is that Mrs. Barrett is always rushing out the door, leaving the house a mess and not giving important information to the sitters (which almost causes Marnie to get very sick). She also repeatedly gets her custody arrangements wrong, which ultimately leads to Buddy getting taken by his father — something that terrifies poor Dawn, as it happens while she's babysitting. It's only after the latter situation occurs that the sitters actually realize that the kids really aren't the ones at fault.
    • Aunt Cecelia spends much of Baby-Sitters Island Adventure blaming Jessi for "allowing" Becca to go off on the boating trip (and alludes to it again in her next appearance), even though it's clearly the Ramsey parents, not Jessi, who would be responsible for this decision.
  • Moe:
    • Mary Anne is the sensitive and sweet flower of the group.
    • Some of the children are considered adorable in-universe and out, most notably Jamie Newton, his baby sister Lucy, Charlotte Johannsen, and the Perkins sisters.
  • Periphery Demographic: The books were aimed at pre-teen and young teen girls, but they have a lot of fans among much older demographics. Justified, as many of those older fans grew up with the books and there's a nostalgia factor involved. Of course, there's also a lot of snark.
  • Rooting for the Empire: Quite a few readers of the Little Sister series cheer for Pamela whenever she gives Karen a bad time.
  • The Scrappy:
    • Dawn has garnered a rather large hatedom in later books. However, many saw her as being Rescued from the Scrappy Heap in Dawn Saves the Planet, where her self-importance and Soapbox Sadie attitude are deconstructed and she gets called out. This resulted in some much-needed development which toned down her negative traits considerably.
    • Karen Brewer is seen by many fans as an insufferable Bratty Half-Pint.
  • Take That, Scrappy!: Dawn Saves the Planet is this to the fans who dislike Dawn (or anyone who dislikes Soapbox Sadie characters in general), especially when it's revealed that most students can't stand Dawn at school, and she briefly becomes The Friend Nobody Likes in the BSC because of her attitude. As a result, she has a Jerkass Realization.
  • Unintentional Period Piece: Setting aside the technological advancements, the series has instances of this.
    • The books were written from the late 1980s to 2000, so many pop culture references, fashion trends, etc. would confuse modern readers. One such example is Claudia's new friend Ashley, who is treated as "totally weird" for wearing long dresses and flared jeans; both of these articles of clothing started to come back into style in the late 90s and early 2000s and, while not fully mainstream, remain in style.
    • In Kristy's Big Day, it's mentioned that Kristy's brother Sam has taken a job at the local A&P (a supermarket chain). The last A&P store closed its doors in 2015.
    • In Boy-Crazy Stacey, the Pike family (plus Stacey and Mary Anne) travel to Sea City, New Jersey for a two-week vacation, and on both the way there and the way home they stop roughly halfway for lunch at a Howard Johnson's. The last Howard Johnson's restaurant in the United States closed in 2022.
  • Unintentionally Sympathetic:
    • In Claudia and the New Girl, Claudia has the nerve to make a friend outside the club, so in retaliation, the other sitters scarf her snacks, short-sheet her bed, leave mean notes around her room (one even suggesting they leave a blank one, just to mess with her head) and trash-talk her in the club notebook which is supposed to be only used for sitting-related entries. It's Claudia who is portrayed as the wrong one and has to apologize in the end. It gets better in the graphic novel where, after Claudia's apology, they all apologize to her too and Stacey admits she should have been a more supportive friend to Claudia.
    • Many readers think the sitters are too critical of Jenny Prezzioso. She's supposed to be terrible and the only baby-sitting charge who is openly disliked by most of the sitters (only Mary Anne kind of likes her). However, she's only 4 years old and, despite being a bit of a Spoiled Brat, readers don't think she's that bad compared to other children in the series. She merely wants to wear nice dresses and not get that messy, and because other charges don't care, she's treated like she's not playing well with others.
  • Unintentionally Unsympathetic:
    • Karen is supposed to be likable because she's intelligent, enthusiastic, and imaginative. Many fans, however, can't overlook her bossy behavior and how often she is an obnoxious, nosy pest.
    • All the main girls can come off as this, depending on the book, since the reader can really only view events through the point of view of whichever sitter is the narrative character.
    • Dawn crosses into this in the 1990s TV series on at least two occasions. One episode has her liking a guy who likes Mary Anne instead; when he calls to ask Mary Anne for a date, he mistakes Dawn for her on the phone and asks out the wrong stepsister. This results in her acting rude and angry towards Mary Anne, whose only crime is being liked by the boy. Another episode has her dating another boy whose mother is part of a group that was going to clear land for a building; she takes her anger out on the boy and cancels their date, despite him having nothing to do with his mother's job.
  • Unpopular Popular Character: Janine is an unpopular smart girl who has very few friends. Her sister Claudia can't stand her most of the time, and also Claudia's friends (at least in early books) tend to think she's an annoying Insufferable Genius and usually try to avoid her. However, fans love her, and she's by far one of the most popular minor characters. It helps that some of the later books give her good Character Development, showing her not just as insufferably smart but also a loyal supporter of her younger sister.
  • Values Dissonance: This is the primary reason that nearly all attempts to revive the series for 21st-century readers have failednote :
    • When the books were first written and published, it was acceptable for a preteen to work as a babysitter unsupervised. These days, one would have to wait until at least their late teens to take on this responsibility, and in some jurisdictions would need to pass a first aid class or receive other certification in order to pursue the widespread child care the club tends to provide.
    • In Goodbye, Stacey, Goodbye Stacey wonders if her parents will decide she's old enough to get some charge cardsnote  when they move back to New York. Who would give a thirteen-year-old her own set of charge cards?! She at most would be allowed — within tight limits — a extension of their cards. (Partially justified in that this is from Stacey's own point of view, and she may not have realized that no, she would not be considered old enough for such a thing.)
    • The overall attitude towards autism in Kristy and the Secret of Susan has aged poorly, and may have been questionable even in the early 1990s, given that Temple Grandin was already famous for her research on animals. Susan's boundaries are completely overstepped in several ways. Kristy doesn't acknowledge that the non-verbal Susan can still understand normal spoken language (in fact, she believes that Susan doesn't understand because Susan never shows any reaction, not realizing that she probably understands a lot and just can't show it) and doesn't allow her to just enjoy doing the things she likes doing (like playing the piano) because she thinks Susan should do what "normal" kids do and never stops to consider Susan's feelings on the matter. Susan is forced to play with the neighborhood children (all of whom treat her like an outcast), which ignores how keeping friends can be difficult even if an autistic person has average intelligence and speech, particularly in adolescence. This is particularly egregious because Kristy is usually shown to be really good about meeting kids where they're at, even with very young children, but she doesn't even seem to try to do the same with Susan. Kristy then tries to guilt-trip Susan's parents out of sending their daughter to a boarding school, which actually had the best resources to help Susan. That said, Kristy eventually admits that her treatment of Susan was wrong and that Susan's parents know what's the best thing for her. The ending also didn't age well, with Susan's mother telling Kristy that she's going to name her yet-to-arrive second child "Hope", implying that she hopes that the new child will be "normal" and not like Susan.
    • Dawn and Whitney, Friends Forever did a slightly better job explaining Down Syndrome, but the first version of the book stated that Whitney was "mentally retarded". The reprint realized how insulting this was and changed it to "has learning disabilities", but that also doesn't quite create an accurate picture because Down Syndrome is an intellectual disability (affecting someone's IQ), not a learning disability (impairing someone's ability to learn in the way that most people do).
      • This book also has Values Dissonance in its basic plot. Whitney's parents essentially hire Dawn to be their daughter's friend, despite having the full knowledge that she wouldn't want someone being paid to spend time with her; and Dawn's behavior towards Whitney is rather patronizing. Today, Whitney's parents likely would get her a professional caregiver if she needed it, and would be encouraged to support her in making friends by herself.
    • Non-fictional Free-Range Children have become a thing of the past, so Mary Anne's father not allowing her to stay outdoors alone after 10 pm would be seen as sensible today.
    • In the second book, Alan Gray is revealed as the one who's been outright harassing Kristy with his hang-up phone calls, which were because he was trying to work up the nerve to ask her out — which she accepts. Never mind that she was genuinely frightened by what was going on before she knew who was behind it; there's also the fact that up to this point, it's been made repeatedly clear that Kristy doesn't even like Alan because he has been bothering and pranking her since (at least) fifth grade. But since "boys tease you because they like you", the harassment can be totally overlooked. This might be one of the worst examples of stalking behavior being portrayed as positive, given that as always, the guy gets the girl. This is probably why Claudia and Mean Janine was chosen to be the graphic novel adaptation from her perspective, instead of this one.
    • The adoption of Emily Michelle Thomas-Brewer. At the time Kristy and the Mother's Day Surprise was published, international adoption was positively perceived by the American public. However, recent years have seen increased awareness of the shady practices of many adoption organizations, the high failure rate of international adoptions in the U.S., and the complicated realities of adopting across racial lines and from one country to another. The series never acknowledges any of this. As a result, Watson and Elizabeth (who are normally portrayed as Good Parents) can seem thoughtless and short-sighted to a modern reader — especially in light of the fact that they have only been married for a matter of months when they decide to adopt Emily Michelle, which (realistically speaking) wouldn't be enough time for the Thomas and Brewer siblings to start feeling like an actual family. The abrupt adoption is shown to have a negative effect on Karen's mental health (which the franchise treats as Karen just needing to get over it), but to modern audiences it just shows how thoughtless Elizabeth and Watson were. In addition to the aforementioned problems with Emily Michelle's overseas adoption from a modern perspective, Elizabeth (in her early to mid 40s) and Watson (in his 50s) would now be considered too old by many agencies to adopt a toddler, or at least encouraged to go with an older child instead.
    • In Kristy's Mystery Admirer, which takes place around Halloween, Mallory says she wishes she could still dress up in a costume and go trick-or-treating on Halloween. Mallory is eleven! Plenty of people older than that have gone out trick or treating, plenty of adults now dress in costumes and have Halloween parties, and costume stores have huge portions just for adult costumes, especially on Halloween!
    • In the first Friends Forever book, Stacey is visiting her father in New York City for a month, and during one of the days she and her boyfriend, Ethan, go to Bloomingdales. Stacey is thirteen, Ethan is fifteen, and they are going into a huge department store in the middle of New York City by themselves! On another day Stacey returns alone to buy some sandals she liked. She is alone, in Bloomingdales, in the middle of New York City, and she is thirteen! Definite Values Dissonance when you consider what New York City is like now!
  • Watched It for the Representation: As told by the documentary The Claudia Kishi Club, released ahead of the 2020 remake, plenty of Asian-American kids and teens picked up the books for Claudia Kishi, the club's airheaded, boy-crazy, and fashion-forward Japanese-American member, for her creativity and non-stereotypical depiction.
  • What Do You Mean, It's for Kids?: The books are aimed at pre-teen girls despite the fact that some of the books deal with racism, divorce, illnesses, death, and at one point, abusive parents. Downplayed though, as the books are still very suitable for children.
  • The Woobie: So many examples, they had to be moved to their own page.

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