| Description | Character |
| The character that most likely creates the most scandal; Dated the boy from Brooklyn, and is best friends with the 'Queen Bee' at Constance. The show starts with her return. | |
| Has a fashion designer for a mother, and is the 'Queen Bee' at Constance. Yale is her constant dream school throughout seasons 1 and 2 | |
| 'Lonely Boy', noted for living in Brooklyn, attends St. Jude's and is largely un-noticed. Creates controversy with a teacher during season 2. | |
| Part of an extremely well-known rich family, that is until season 2, where his father causes them to go bankrupt. He has basically made out with every girl on this show. | |
| Also lives in Brooklyn, strives to be noticed and become a fashion designer. Fights often with her father and in season 2, she runs away. | |
| Best friend of 'Lonely Boy', often interferes in business that is not her own. | |
| Classy, rich boy who has only had one girlfriend on the show, but during seasons 1 and 2, was always waking up with a new girl beside him. He thought his mother died in childbirth | |
| Mother of the main character on the show, during season 2 there was an episode about her youth. Divorced many times. | |
| Extremely successful businessman, father of the classy, rich boy, dies in season 2. | |
| Neglegent father of the two kids that live in Brooklyn, both of his marriages on the show have been disastrous. | |
| Maid in the house of the fashion designer and the fashion designer's daughter. | |
| Gay brother of the main character on the show, beginning of season 1 revealed that he tried to kill himself. | |
| Fashion Designer who ends up marrying the guy from Princess Bride after her first husband turned gay. | |
| Re-occurring guest star who created extreme controversy with the main character in season 1 involving a murder, and in season 2 involving a lost love child. | |
| Drug addict that caused his family to go bankrupt. | |
| Stole a baseball from the classy rich boy in season 1, stole money from the rich famous boy in a round of poker in season 1, and stole the heart of the main character in season 2 | |
| One of the 'Queen Bee's' sidekicks, she is basically the only black person at Constance and on this show. | |
| The French partner of the father to the girl who dreams of Yale in the Christmas episode of season 1. She doesn't like him at first. | |
| Also dreams of Yale, until social status becomes an important aspiration for this Chinese student at Constance. She's always on a different side, and was sabatoged during her SATs. | |
| The girl from Brooklyn stole her mother's Valentino dress so she could wear it for her birthday. | |
| Grandfather of the rich boy who goes bankrupt. | |
| 'Helps' the girl from Brooklyn with her fashion career until she burns all of her designs. | |
| | Description | Character |
| The only gay boyfriend the main character's brother ever had on the show | |
| Never liked the idea of her granddaughter (main character) being with the boy from Brooklyn, until the beginning of season 2 | |
| This is the secret love child. | |
| Played by re-occurring guest star Hilary Duff, she attends NYU in season 3 and dates the boy from Brooklyn. | |
| Drug dealer in season 3 that the girl from Brooklyn likes. (He is using her to help sell drugs) | |
| The main character's real father that has never been on the show. | |
| Psycho-mom of the family that has gone bankrupt due to her husband's drug problem. She takes a long time to admit when things are going wrong for the family. | |
| Jewish man that eventually marries the fashion designer. Has a son that dates the main character. This is the guy from The Princess Bride. | |
| An artist that dates the main character in season 2, and tries to save their relationship by taking her to Buenos Aires. | |
| The principal at Constance. (Give 'title' along with last name) | |
| In season 1 she is the wife of the ex-rock star from Brooklyn that went to Hudson (and stayed in Hudson) but eventually they get a divorce when he falls in love with a former gf | |
| The fashion designer's first husband, until he left her for a male model. | |
| Celebrity that befriends the main character at a fashion show and gives her official celebrity status. She creates controversy with the guy who scams people out of their money. | |
| Starts off season 3 by dating the once-bankrupt boy, but their relationship inevitably ends when they reveal their last names and find out their families are serious rivals. | |
| Sidekick of the Queen Bee, one of two Asians on this show. She is moved back to Israel by her parents after spring break. | |
| Duchess. | |
| Woos the fashion designer's daughter in season 2 with his title, has an accent and is pure royalty. Has an affair with his step-mom that ends his American relationship. | |
| In season 2, he dates the main character and scams pretty much everybody out of their money. | |
| Rescues the classy rich boy from a foreign country after his father died, and something happened between him and the Queen Bee during season 2 (New Years) | |
| New, young teacher at Constance that the main character thinks is super awesome, until she has an affair with her ex-boyfriend. | |
| Very involved in politics, he was elected to Congress in season 3 and had an affair with the main character. | |
| Dated the girl from Brooklyn during season 1, played lacrosse, and turned out to be gay. | |
|