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Played by: Josh Holland
- Book Dumb: Mostly because he couldn't care less about school lessons. He's also stated to be often Late for School... on his better days.
- The Casanova: Is known as the top womanizer of the entire school.
- Chick Magnet: When he's not chasing girls, they will chase him.
- Expy: A blonde troublemaker and casanova like Zack Morris from Saved by the Bell
- Lack of Empathy: Played for Laughs in one episode, when his friends complain about it. He learns to be more sensitive and empathic but he goes overboard, getting a We Want Our Jerk Back reaction.
- Lady Killer In Love: Even if he is The Casanova, he genuinely falls in love with Lauren.
- New Transfer Student: Introduced as this in the pilot.
- Only Sane Man: Oddly enough, he's the most levelheaded of the three main guys.
- Unresolved Sexual Tension: With Lauren, whenever they are not dating.
Played by: Elena Lyons
- Brainy Brunette: More intellectual than all her friends, at least. She also has much more common sense than Dumb Blonde Ashley.
- Deadpan Snarker: Shares this role with Winnie. Both are equally snarky, but Lauren is more deadpan.
- Dude Magnet: In one season 2 episode, she actually complains about having too many boys asking her out.
- Ms. Fanservice: Lauren is the glamorous leggy brunette, whose actress Elena Lyons made it onto Maxim's Hot 100 List in 2005.
- Only Sane Woman: The closest to a reasonable person in the group.
- Unresolved Sexual Tension: With Jackson, whenever they are not dating.
Played by: Thomas Magiar
- Beta Couple: With Winnie. They are a much more stable couple than Jackson/Lauren.
- Book Dumb: In one episode he needs to be tutored by Winnie, which was also the start of their relationship.
- Brainless Beauty: A male example, merging this with Dumb Muscle and Dumb Jock.
- Chick Magnet: Quite a few girls tried to steal him from Winnie. Needless to say, she didn't take it well.
- Dumb Jock: A basketball player who is not very smart.
- Expy: A hunky jock like Slater from Saved by the Bell. Though he has no rivalry with Jackson (Zack's expy).
- Kindhearted Simpleton: A Dumb Jock who is pretty much well-meaning, loves Winnie, and is a loyal friend.
- Mr. Fanservice: Christian is a German muscleman who frequently appears shirtless.
Played by: Marquita Terry
- Beta Couple: With Christian. They are a much more stable couple than Jackson/Lauren.
- Black Best Friend: To both Lauren and Ashley.
- Clingy Jealous Girl: She will kill any girl who tries to make a move on Christian.
- Dating What Daddy Hates: She mentions her father never liked any of her ex-boyfriends.
- Deadpan Snarker: She and Lauren are both the snarkiest characters. Although Winnie is much less deadpan.
- The Dreaded: She's so aggressive that a lot of people are scared of her, even her boyfriend Christian.
- Sassy Black Woman: Black, feisty and hugely aggressive.
- Token Minority: The only black character in the first season. In season 2, she shares the role with Excess.
- Tsundere: In the first few episodes, she claimed to hate Christian. When they get together, she mellows out and warms up to him but she is still very much this trope when she gets angry (Christian is still scared of her).
Bobby "Lazz" Lazzarini
Played by: James Madio
- Big Applesauce: Lazz is from Brooklyn.
- Big Eater: Especially when it comes to meat.
- Book Dumb: He once said that C- is the highest grade he ever got.
- Butt-Monkey: He is often teased by his friends and has a tendency to get girls using him for their ulterior motives.
- Casanova Wannabe: Shamelessly hits on girls, but he's not successful at all.
- Hollywood Dateless: He's supposed to be a loser who never gets girls. He actually has several one-shot girlfriends and dates throughout the show. Some of them were just using him, but others were genuinely interested in him and just disappear the next episode. A girl even picked him over Jackson. Then there's Ashley
- Hopeless Suitor: To a lot of girls, including his teacher Ms Dupree.
- Last-Name Basis: Usually called Lazz, which is short for his last name Lazzarini.
- Plucky Comic Relief: The Class Clown who is the most prone to wacky antics.
- Put on a Bus: After season 1, Lazz goes back to Brooklyn to spend some more time with his family.
- Trademark Favorite Food: Meat.
Played by: Kristen Miller
- Cloudcuckoolander: She is very spacey and prone to illogical thoughts that make no sense.
- Cute and Psycho: A cute blonde Nice Girl but has several unstable Mood-Swinger moments.
- Daddy's Girl: Ultimately, she and her father are very close.
- Dating What Daddy Hates: In one episode she dates Lazz just to piss her father off. She ends up liking him for real, but it was one-sided and she gets over it...until the season 1 finale.
- The Ditz: The ditziest of the group.
- Dumb Blonde: Blonde-haired Ashley isn't the brightest bulb.
- Expy: A British Phoebe Buffay in almost every way.
- Friend to All Living Things: To the degree where she rescues a chimpanzee in one episode and tries to hide it from her father.
- Genius Ditz: Possibly. It's mentioned she gets good grades, but according to Winnie, it's only because her father is the Headmaster (it is not clear if she was joking). Ashley is also very good at drawing, in contrast to Lauren.
- Hair of Gold, Heart of Gold: Ashley is blonde and therefore kind and considerate.
- Hollywood Dateless: Very much Depending on the Writer. In some episode of both seasons, she is sad because she is unlucky in love and the only one without a date. In many other episodes, she easily gets dozens of boys falling at her feet, sometimes literally (going to a school dance with six boys at the same time).
- I Am Very British: Ashley and her father speak with very posh RP accents.
- Tsundere: Normally friendly and innocent, but she can get scarily rude and aggressive out of nowhere.
Miss Gabrielle Dupree
Played by: Angela Visser
- Cool Teacher: The girls frequently go to her for help.
- Everyone Loves Blondes: Blonde and a Lust Object for the male students.
- Everything Sounds Sexier in French: She has a French accent in early episodes.
- Hot Teacher: All the male students have the hots for her.
- Unresolved Sexual Tension: With Mr Elliot, Depending Onthe Writer. It sometimes seems one sided on his part. They eventually get married.
- Women Are Wiser: More levelheaded than Mr Elliott.
Headmaster Patrick Elliot
Played by: Nicholas Guest
- Cannot Spit It Out: When it comes to his feelings for Miss Dupree.
- Former Teen Rebel: Jackson in the pilot ruins the school uniforms by pouring red dye in the washing machine. After Mr Elliot decides to get rid of uniforms altogether, he says to Jackson "I used a lot more red dye".
- I Am Very British: Like his daughter, he speaks with a very posh RP accent.
- Not So Above It All: Lazz falls out of a window watching Ms Dupree changing and sues the school for the injury suffered. At the end of the episode Mr Elliot falls out the window for the same reason.
- Overprotective Dad: Sometimes to the point of trying to manipulate Ashley's social life, because he believes he's the only one who knows what it's good for her.
- Reasonable Authority Figure: He may be stern but ultimately not a Dean Bitterman.
- Unresolved Sexual Tension: With Miss Dupree. It sometimes seems one sided on his part. They eventually get married.
Dwane "Excess" Wilson