Before Jenna Hamilton’s ‘Awkward.’ Arrest, Let Us Celebrate 5 Other Good Girls Gone Bad

Arrest

The drain is ripe for circling, and the “Awkwarddownward spiral you’ve been dreading is starting to take shape. On the show’s next episode, after having been abandoned by her friends in the aftermath of her breakup with Matty, Jenna Hamilton will commit to a rebellion that culminates in a car filled with what distinctly resembles a reefer cloud. Cue a few flashing police lights in the background, and J-Ham’s made an official transition to the dark side.

By the looks of things, Jenna will be knee-deep in fast times for much of the season, but we’ve seen angels devolve into demons before, and quite often they return to their senses after a brief brush with rock bottom. There’s hope for Jenna yet! But we’ve got a long road ahead of us, folks, so in the meantime, take a look back at five of the greatest girls gone bad.

Cady Heron, “Mean Girls” — Cady, who was home-schooled in rural Africa until halfway through high school, was as unassuming as they come when she first set foot inside a public classroom. When she agreed to help a fellow student exact revenge on a known mean girl, though, she found herself wrapped up in the popular crowd’s superficiality, and quickly became the Plastic she’d originally intended to take down.

Rory Gilmore, “Gilmore Girls” – The valedictorian and Student Council President who’d essentially sworn off sex, drugs and rock ‘n roll from birth tapped into her dark side when she got a taste of post-high school freedom. Within a year, Rory slept with her married ex-boyfriend, dropped out of college indefinitely and…oh, yeah, was arrested for STEALING A BOAT. She ultimately graduated from an Ivy League school and became a political reporter, though, so we guess you can say she reformed…

Mary Camden, “7th Heaven” — When you’re actually a preacher’s daughter, there’s a certain level of morality that’s expected of you, and Mary was able to stay on the straight and narrow until her senior year, when her grades started to slip. Soon, she was suspended from the basketball team and sought revenge by vandalizing the school’s gym. Things went downhill from there as Mary started drinking and neglecting her responsibilities at various jobs, and eventually, her parents had no choice but to ship her off to her grandfather’s place in hopes he could help her reform.

Lizzie McGuire, “Lizzie McGuire” – When they say “If you can’t beat ‘em, join ‘em,” it’s not usually meant in reference to school bullies. In an effort to get a mean monkey off her back, Lizzie joined the likes of a notorious party girl (and even got a clip-in nose ring!), and when she appeared to have completely gone off the deep end, her pals staged an intervention to bring her back to her old self.

Sandy Olsson, “Grease” – Call her the prototype. The virginal Sandy Olsson appeared to have been sent straight from heaven when she found her way to Rydell High School — that is, until she started dating the school’s infamous T-bird, Danny Zuko. When she realized things would never work between them as they were, she ditched her poodle skirts for some tight leather pants, lit up a cigarette and joined the dark side, otherwise known as the Pink Ladies. That’s where the movie ended, at least — something tells us Sandy woke up the next morning clutching her stuffed elephant and a bottle of makeup remover.

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