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.
Kate Gavino lives in Brooklyn with her narcoleptic dog and piles of books. She has written for sites like HelloGiggles, The Airship, Prefix Magazine, and CMJ. She also plays tournament Scrabble, takes walks with senior citizens, and comes up with punnerific trivia team names. Follow her on Twitter: @kategavino. This piece was originally published on xoJane.