Evelyn Cummings | | Age seventeen, a high-achieving senior, often stressed-out. She enjoys writing but is not sure what she wants to do with her life. She has been dating Jared for two years. Her mother nags and pressures her to succeed. |
Jared Jamison | | Age eighteen, a cool guy everybody likes. He has strong leadership skills and plans to attend East Point, a military academy. He has been dating Evelyn for two years. He does not get along with his father, who disagrees with his career choice. |
Olivia Grenson | | Age eighteen, popular senior at Erma Schmoe, and a song writer. She wants to be a Hollywood star and models her life after the famous party girl, Vienna Marriott. |
Babbers | | Age eighteen (probably'no one knows), a low-achieving senior, a spaced out slacker. He randomly makes comments about life that are either incredibly deep, totally ridiculous, or both. |
Lily | | Age seventeen, an environmentally-conscious senior from a family of modest means, who is sick of the pre-college rat race. |
Melanie | | Age eighteen, a very wealthy senior, who admires Olivia, doesn't care much about school, and figures that her family money will solve any possible problem. |
Clif | | Age eighteen, a jock senior who plays every imaginable sport and feels the senioritis burn. |
Dexter | | Age seventeen, a tech-genius senior who applies his nerdiness to various academic endeavors. |
Timmy | | Age fourteen, an annoying freshman who is dating Olivia. Seniors like to punish him for his immaturity by shoving him into lockers. |
Agent X (Siren 1, College Girl, Liecht) | | Age eighteen, a high school senior from Liechtenstein. She pretends to be a senioritis expert as a plot to get into a Holly League college. |
Agent Y (Siren 2, College Girl, Stein) | | Age eighteen, a high school senior from Liechtenstein. She is Agent X's partner in crime. |
Stanley Krasston | | Age fifty, the assistant principal at Erma Schmoe, very hyper and controlling, having learned his disciplinary methods at a dog obedience school. He holds a grudge against Meg Wivvans, a former high school classmate who got into a college (Pennvard) that rejected him. He still lives with his mother. |
Meg Wivvans | | Age fifty, the principal at Erma Schmoe, a complete clueless ditz, an ex-hippie (and Pennvard grad) who believes in spreading love and happiness. Superintendent Hawkins placed Krasston at her school to keep her in check. |
Dr. Helga Hawkins | | Age fifty-five, the superintendent of Schmoetown schools. She is strict and imposing, but can be dry and sarcastic when making her no-nonsense decisions. |
Austen Bronte | | Age forty, a English teacher who enjoys teaching. He has high integrity but is not particularly courageous. |
Raspy Gaspy | | Age sixty-five, a choir teacher, a chain smoker with a gravelly voice, who hates how students look upon her class as an "automatic A. |
Felicity Forte | | Age thirty-five, a drama teacher who wants students to be creative, no matter what that requires. |
G.C. Beaker | | Age thirty, a science teacher who wants new scientific results, no matter what that requires. |
Napoleon Charlemagne | | Age forty, a history teacher who wants students the appreciate the hardships of human history, no matter what that requires. |
Darryl Darrington | | Age fifty, the founder and president of CollegePlank, slimy, always looking out for his own interests first. |
Cornumbia | | Age forty, college admissions official, preppy, a Holly Leaguer and proud of it. |
Pennvard | | Age forty, college admissions official, preppy, a Holly Leaguer and proud of it. |
Browston | | Age forty, college admissions official, preppy, a Holly Leaguer and proud of it. |
Yalemouth | | Age forty, college admissions official, preppy, a Holly Leaguer and proud of it. |
Julie Cummings | | Age fifty, Evelyn's mother, up-tight helicopter-parent. She desperately wants Evelyn to succeed, and thinks Jared is a negative influence on her schoolwork. |
Finbar Jamison | | Age fifty, Jared's father, judgmental, disapproves of Jared's decisions, especially his intention to accept admission at a military academy. He thinks Evelyn is a negative influence on his choices. |
Bobby Babbers | | Age fifty, Babbers's father, a laid-back ex-hippie who worships his son, whom he thinks has the makings of a great philosopher. |
Ophelia Grenson | | Age fifty, Olivia's mother, who thinks, acts, and dresses like she is still a teenager, often very inappropriately. |
Mom Krasston | | Age seventy, Krasston's mother, who loves her son and is a little demented. |
Madonjelina | | Age thirty, Hollywood's biggest star, sinfully wealthy, loved by everyone for her global philanthropy. She has launched a contest for a high school student to be her "celebrity assistant" and has proclaimed her intention to adopt "a torn and tattered teen." |
Terri | | Age twenty-five, Madonjelina's assistant, fawning toward her and sarcastic toward all others. Always present wherever Madonjelina goes, he translates her wishes into real bottom line demands. |
999 Misery Way | | A dancing human mailbox that gleefully delivers college rejection letters to high school seniors. |