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Stoneybrook, Connecticut may have been an idyllic town where the Baby-Sitter’s Club giggled about boys, doodled horses, and played hopscotch with kids, but Ann M. Martin’s wholesome characters sometimes found themselves in some tricky situations. The series would go on to have spin-offs like "The California Diaries" that dealt with more mature themes head-on and without tidy resolutions, but there was nothing quite like the original series, that handled such issues with kid gloves and high-minded morals.
Here’s a list of the best moments where the PG-rated sitters verged into some PG-13 (-ish) territory. Mallory fans: you may need to sit this one out.
1. Kristy + Bart = ?
As the BSC’s fearless leader, Kristy was not one to break any rules, but when she did, she swung for the fences. When her longtime crush and rival softball coach, Bart Taylor, invited himself over one Saturday night to “watch the game,” things turned steamy fast. In the midst of tongue-wrestling, Kristy’s mom and stepdad walked in and sentenced her to a weekend imprisoned in her bedroom.
If this was "Gossip Girl," Bart would have found a way into her bedroom and into her softball shorts, but since this is the BSC, the book ends with them putting on a talent show together with a bunch of kids. Huh. Still, the fact that the holier-than-though BSC president was still a victim of hormones is delightfully refreshing.
2. Dawn and the We Love Kids Club
Consider this a crash course on credit card fraud. Dawn, ever the flip-flopper, is torn between California and Stoneybrook. Since she’s on the West Coast for now, she decides her heart belongs in the suburbs after her dad announces his engagement to his latest whitebread girlfriend.
Dawn steals her dad’s credit card, books a one-way plane ticket (quaintly done over the phone), and returns to the land of charity car washes and snowball wars. There was some serious brass balls on display in this book, especially from save-the-earth, hemp-wearing Dawn, but of course, it’s all washed away the moment the "Full House" music comes on and Dawn learns a very important lesson on identity theft.
3. Mary Anne Breaks The Rules
Mary Anne may have been the BSC’s meekest member, but the fact that she had a Southern-fried bohunk for a boyfriend was something she probably lorded over the rest of the club. So she decides to bring him to a baby-sitting job one day because she thinks the kid needs a “male role model” in his life. Sure, Mary Anne, whatever you want to call it.
The kid’s mother comes home and assumes some hanky-panky is going on, and from then on, Mary Anne is branded as the village tramp. Again, the story wraps up quickly and conveniently in the end, and MA gets her good name back, but you’d think the BSC would have a hard and fast no-boyfriend-on-the-job rule from the start. This is a business, not a brothel, Kristy.
4. Dawn and the Older Boy
The BSC has tangled with older boys before (see: Stacey, Stacey and more Stacey), but none have been as nefarious as Travis. Once he and Dawn confirm their soulmate status by the fact that they have both spent time on beaches, they go straight into Tina-and-Ike mode (minus the cocaine nosebleeds). He gives her some unsavory fashion advice, cloaks her in his varsity jacket, and horror upon horrors, takes the future PETA-spokeswoman to a place called Burger Bite.
Then it turns out that Travis never considered them an item and instead saw Dawn as something of a makeover project. At that, Dawn should have gone full on Laney Boggs, but instead, she turns her attention to a cuter, age-appropriate pen-pal.
5. Keep Out, Claudia
Any time the BSC has dealt with social justice issues, a certain level of restraint is present. In this book, the issue (“Racism sucks.”) is presented through the club’s resident fashionista. Claudia has been singled out because of her wardrobe (acid-wash overwalls, anyone?) but never because of her race.Needless to say, she’s shocked by a client who refuses her services because of her “almond-shaped eyes.”
Jessi, a character who is often characterized by her “cocoa-colored skin,” gets a door literally slammed in her face and simply rolls her eyes at the Connecticut-ness of it all. At one point, lily white Mary Anne takes the job and mentions Mallory’s sprawling family, the kid says, "She must be Catholic." Stoneybrook, meet Archie Bunker.
6. Kristy’s Mystery Admirer
You can always count on Stoneybrook’s #1 shit-stirrer and BSC arch-nemesis, Cokie Mason, for a good spot of trouble. When Kristy starts getting notes from a secret admirer, she’s flattered and secretly hopes it’s from the Bart-man. That is, until they turn into death threats. (“Violets are blue, blood is red, I’ll remember you when you are dead." Way to mess up that meter, Cokie.)
Cokie quickly veers into Single White Female territory when she starts sending Kristy fingernail clippings and mentioning “eternal togetherness.” The book ends with Cokie getting her comeuppance and Kristy and Bart going to the Halloween dance together as lobsters. Again, if this was "Gossip Girl," someone would’ve gotten shanked.
7. Stacey and the Bad Girls
There’s a reason why Stacey was such a popular character. She knew how to bring the drama, and not just in the form of diabetic shock. She always had the best boy-related books (Boy Crazy Stacey, anyone?), and thanks to her sophisticated New York City reputation, her bustline was always well-documented.
One of the most scintillating story-lines in the series was when Stacey quit the BSC to hang out with her jock boyfriend and her other flannel-wearing (read: alternative) friends. This leads to her experimenting with light shoplifting, black lipstick, and getting kicked out of a concert with a flask. Sadly, this doesn’t lead to a weekend bender that ends in a Tijuana holding cell, but instead, with Stacey running back into the arms of the BSC.