Josie ultimately learns important lessons about being proud of who you are -- and that being true to yourself and your friends matters more than fitting in. There's also a strong theme about it never being too late to start over/try again. But there's also a lot of dishonesty in the story, and some of the attractions/flirtations between characters who aren't quite what they seem (twentysomething/teenager, and teacher/supposed student) can be uncomfortable.
Positive Role Models & Representations
Some comic pratfalls, etc. A character throws eggs at another character.
Kissing and lots of flirting -- some of it between characters who would have problematic age differences if they were all telling the truth ("teenage" Josie and a teacher, Josie and her brother and actual teenagers). In a scene in which high schoolers are meant to learn about sex ed, they're shown putting condoms on bananas (with references to "the real thing"), and anatomical models are shown. A supporting character frequently discusses her sex life (with some lewd gestures/references) and is implied to sleep around. Teen characters talk about sex/losing virginity. Some skimpy/tight outfits on teenage girls.
A couple of uses of "s--t," plus "oh my God," "ass," "hell," "goddamn," and "damn."
The Chicago Sun-Times and Tribune newspapers are mentioned frequently (Josie works for the Sun-Times); Josie talks about her car by its brand name (Buick).
Ease of Play
Josie unknowingly eats a pot brownie and gets very high/silly -- the scene is played for comedy. Teens drink at a party, and a teen girl who's acting goofy during prom admits to having had some champagne. Some background smoking and beer drinking by adults.