Who is Rosalyn?

Rosalyn is a high school student and Calvin's official babysitter whenever Calvin's parents need a night out. She is the only babysitter able to tolerate Calvin's antics, which she uses to demand raises and advances from Calvin's desperate parents. She is also, according to Watterson, the only person Calvin truly fears—certainly she is his equal in cunning, and doesn't hesitate to play as dirty as he does. Originally created as a nameless, one-shot character with no plans to appear again, Watterson decided he wanted to retain her unique ability to intimidate Calvin, which, ultimately, led to many more appearances.

Rosalyn's idea of effective babysitting is a 6:30 bedtime for Calvin, and she has little patience for his attempts to rebel against her. Calvin will often freak out whenever he hears that Rosalyn is going to be babysitting him, in one instance screaming in protest non-stop for an entire strip. In the final Rosalyn story, however, the traditional war is averted by a game of Calvinball, in which Rosalyn proves to be a formidable player, and once again trumps Calvin with a clever move in the last panel. This display of extensive imagination showed her to be not entirely lost to the dull world of adulthood, and this trait allows her to sympathize with Calvin's needs and ultimately control him much better than his mother ever could, such as in the same storyline as above, in which she allows him to stay up half an hour past his bedtime, and plays Calvinball with him, two actions which Calvin's mom would be sure to avoid (ironically, on returning home, Calvin's parents refuse to believe that she was able to play a game with him, and assume she is making a joke). Occasionally, Calvin manages to gain the upper hand by tricking Rosalyn into devious situations, such as locking her out of the house.

In nearly all the "Rosalyn stories", Roz is shown demanding advance payment and raises in wage from Calvin's parents, supposedly because she needs the extra money to pay for college. (For exactly the same reason, she briefly appears as Calvin's swimming instructor.) They are reluctant to pay such exorbitant rates, but even more unwilling to have a dinner without "real pauses in the conversation." Therefore, they always gave Roz her raise.

In at least four stories, Rosalyn telephones her boyfriend, Charlie, to cancel prearranged meetings which she cannot fulfill. (Charlie remains as an unseen character.) Calvin sometimes breaks in and urges Charlie to stop courting Rosalyn, asserting that Rosalyn is either sadistic or insane, or both.

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