Lanie's step-father, a conservative career politician who ultimately becomes the short-term mayor of Palm Beach.
- Big Bad: Once Jamison succeeds in becoming mayor of Palm Beach, he pretty much becomes this for just about every character who isn't straight or over the age of twenty-one. He's also probably the most successful villain the site ever had.
Alfred "Jerry" Coogan
A bullying senior jock who plays linebacker on the Palm Beach High School football team.
- Anything That Moves: He allowed Xavier to give him a handjob once, and claimed that he was "gay for fifteen minutes", but that those fifteen minutes had since passed.
- Disc-One Final Boss: Jerry was about as much of a direct antagonist as EWO had, when he was alive. However, the scope of his misdeeds were limited to the context of High School and he died early on enough that Jamison tends to get remembered more as the "bad guy" than he does.
- Jerk Jock: A very good football player and wrestler, but universally recognized as a massive jerk, even to his closest friends.
- Pet the Dog: A very small one from just before he died- When Travis allowed him to stay in his guest room, the two came about as close as they would really get to verbalizing how much they valued each other's friendship.
Zara's mother, a professional party planner.
- Jerkass Has a Point: Ana often raises pretty legitimate points about Zara's behavior, and treatment of the people around her, that tend to go unnoticed because they're framed as coming from an abusive bitch instad of a parent at the end of her rope.
Zara's father, a successful lawyer.
- Bunny-Ears Lawyer: While he's certainly a tad.... eccentric at times, he's also very clearly one of if not the best lawyers in Palm Beach.
- Reasonable Authority Figure: One of the few in Palm Beach. Whatever else can be said about him, he's generally a reasonable guy who usually makes a point of acting logically instead of emotionally.
A 19-year-old Russian-American from New York, Bulgarin initially moved to Palm Beach and began working as quite possibly the town's most notorious drug dealer.
- All Guys Want Cheerleaders: He used to go to football games just to watch Zara.
- Genius Bruiser: While he might just look like Dumb Muscle and it's certainly joked about, Bully is clearly very adept at math and science, to the point of being able to tutor Zara in math and being able to figure out how to produce his own drugs without much in the way of formal training.
- Hidden Depths: He's definitely got a nicer, more caring side to him than one might initially think, and he's far more intelligent. Not that he hides it, it's just occasionally easy to lose sight of.
Jason and Matt's mother. She had the both of them as a High School senior, and splits her time between being a sporadically-employed hairdresser and the town drunk.
- Maternally Challenged: She tries, but Cassie simply isn't suited to being a parent.
A shy, submissive 16-year-old girl, born on Staten Island. Reasonably new to Palm Beach and raised in a stuffy, sexually-repressed Victorian environment.
- Buxom Is Better: While Rissa isn't overly fond of her curves, both Jason and Zara seem to like them a lot.
- Dating What Daddy Hates: Jason is the poor, unrefined son of the town drunk, the complete opposite of the kind of guy Virginia wants Rissa associating with.
- Progressively Prettier: She's initially described as being very mousey and plain. As time has went on, it's fairly clear that nobody ever really thought of her as being remotely unattractive, just strange and oddly dressed. This is especially clear in Grapevine Fires, where she's considered one of the most attractive girls in town upon arrival, even being compared to a Disney princess.
- Puppy-Dog Eyes: She's got a particularly lethal pair of large blue eyes, which she's very much weaponized.
- Put on a Bus: Grapevine Fires ends with her finding out that she's moving back to New York to be closer to her extended family and new fiance, and the last thing to happen is her telling Jason, after having put it off for a month.
- Spock Speak: As a result of her upbringing, she speaks in a very proper manner and is literally incapable of using contractions.
A meek, reserved 17-year-old High School junior who's extremely close to his mother.
- Anything That Moves: Daniel shows interest in just about anyone who'll give him attention, regardless of gender or sexuality.
- Nerds Are Virgins: Initially played straight, then defied. He's arguably more of a Clueless Chick Magnet than Jason is, and he's had plenty of love interests (and sexual partners) of both genders as time went on, oftentimes even because of his dorkiness. To date, he's even actually been part of two love triangles and the center of a Love Do Decahedron involving Xavier, Peyton and Teddy.
A 19-year-old from Chicago, a star player on the Palm Beach High football team and a man with plenty of interesting connections.
- Cartwright Curse: An inordinate amount of Darian's love interests have been killed off, or disappeared without a trace.
- Glass Cannon: Although he's an excellent fighter, Darian is also very likely to be nicked up or injured a lot of the time.
- Handsome Lech: Darian is somewhere between this and Casanova Wannabe. While he's certainly not unsuccessful with the opposite sex, he tends to try much harder than Bully or Jason and, while he's rarely unsuccessful, seems to have a lot more trouble holding down long-term relationships.
- Politically Incorrect Hero: Although he's bisexual, Darian has been known to pepper his speech with the occasional homophobic slur.
The captain of the Palm Beach High School cheerleading squad and a talented gymnast, Lanie's main struggle is with his feelings for his best friend and his abusive, politician step-father.
- Boomerang Bigot: Lanie is about as homophobic a gay person as you're likely to find, although it's not always obvious.
- Straight Gay: Less stereotypically "gay" than Boone as a product of Jamison trying to force him into being "straight".
Clarissa's closeted older brother, who hangs out most commonly with Jerry and Travis.
- Jerk with a Heart of Gold: While he's capable of being just as much of a dick as Jerry or Travis, he's very obviously got a soft spot for his younger sister.
A 15 (later 16)-year-old High School sophomore, and cheerleader.
- Broken Pedestal: Jac is absolutely convinced that Jason is 100% completely perfect, no matter how abrasive or irritated he would get with her for thinking so until she finds out about Fight Club, and the ensuing fallout causes their relationship to end on a horrible note.
- Clingy Jealous Girl: Clingy, absolutely. And unfailingly suspicious of Jason and Rissa's friendship, though perhaps not without good reason.
- Teens Are Short: Jac is about the same height as Tiffany, at roughly five feet.
A 17-year-old Palm Beach native, whose mother is the town drunk. Jason himself is a recovering alcoholic, and attempting to use sports as a way up in the world.
- Book Dumb: Jason is a poor student, with several glaring gaps in his education due to spotty attendance, who needs lots of tutoring just to be able to stay academically afloat.
- Determinator: One of his defining traits. He's a big-time workaholic, which is suggested to be a displacement for his addiction issues, and very good at shaking off illnesses and injuries when he doesn't want to waste time recoving.
- Hilariously Abusive Childhood: Although Cassie's verbal abuse and emotional manipulation are usually played as being fairly serious, his stories about his early childhood do tend to veer into this territory from time to time. For instance, while changing his fake rubber baby, he suggests just running it under very cold water when he can't find any baby wipes. Rissa thinks he's just being funny, but the ensuing post hints that it actually was something Cassie did when he was a baby.
- Lightning Bruiser: He's built like a brick shithouse, but able to cover ground like a sprinter.
- Tall, Dark, and Snarky: Well over six feet tall, dark-haired, noted by most people he comes across as being rather hunky, and entirely too sarcastic for his own good.
- Troubled, but Cute: Considering he's fairly oblivious, he definitely attracts a lot of female and male attention. He gets arrested and thrown in the drunk tank at one point, and judging by Cassie's reaction to bailing him out, it's not the first time.
Jason's manipulative twin sister, and a disaffected party girl with no real aspirations for her own future.
- Can't Live With Them, Can't Live Without Them: Although she often snarks at her brother, and acts rather coldly toward him, she takes the idea that he might leave her behind to go to college rather hard.
A well-off junior who's interested in Zara.
- Butt-Monkey: He "loses" Zara to Bully, loses the Homecoming Prince election to Jason — who not only didn't campaign at all, but had no idea that he was even entered to begin with until his name was called — gets groped by Slenderman, and the plane tickets he bought for himself and Zara wound up being used to send Bully and Zara to France, instead.
- Informed Flaw: Zara routinely complains about his insufferable arrogance, but he's not particularly confident to begin with and tends to fade into the background in her interactions with Bully.
An extremely short cheerleader with a lot of interest in sports.
- Teens Are Short: Tiffany is easily the shortest character in the entirety of the in-game university at a hair over five feet tall. She was also previously involved with the second-tallest character in the game.
An apparently meatheaded senior jock at Palm Beach High School who thinks the only things that matter are him and his car.
- The Charmer: He can surprisingly charming when he's not busy being a massive Jerkass, and even sometimes while he's being a massive jerkass. Generally just when he wants something from someone, though.
- Condescending Compassion: Although she's not consciously discriminatory, Virginia is often rather unintentionally xenophobic- She assumes that Bully's english is poor, for example, because he happens to speak with a mild Russian accent.
- Statuesque Stunner: Even well past the age of seventy, Virginia is rather striking — Most notable by the fact that, at five-foot-ten, she is canonically the tallest female character in the entire EWO universe. It also puts her head and shoulders above her 5'3" daughter, and just about on eye-level with her 6'2" son.
The least popular student at Palm Beach High School, and the former president of the Gay-Straight Alliance.
- Hidden Depths: Despite his rather simple nature, Xavier is a surprisingly adept photographer, and actually shows a good amount of promise as a filmmaker. He's also an accomplished liar and a surprisingly capable schemer when the need arises.
The Queen of Palm Beach High School, she starts out as a co-captain on the cheerleading squad and an active member of more clubs than one could probably count.
- Broken Ace: She's popular, well-liked by the student body, intelligent and highly involved in just about everything, but she's got more than her share of crippling family and self-esteem issues.
- Put on a Bus: Between Grapevine Fires and Our Next Chapter, she moves away to go to boarding school in Connecticut. Although she and Rissa continue to maintain contact, they never wind up returning to what their friendship used to be.
- "Well Done, Son!" Guy: A lot of her motivation is to prove her worth to her very difficult-to-please mother.
The youngest Brightman brother.
- Love Makes You Dumb: Aedan continually takes Teddy back in spite of the fact that the older boy is openly manipulating him, regularly cheats on him, and is very obviously an emotionally abusive, suicidal heroin addict. He does grow out of it later, however.
- Emo Teen: Although he's not exactly prone to dressing darkly, he entered an RP that already had it's fair share of Wangst and quickly established his claim to the Wangst Throne with his near-constant complaining about his life and how misunderstood he is by his siblings and father.
- Informed Ability: The Brightmans are touted (mostly by themselves) as excellent musicians with a legion of adoring fans but Aedan in particular is rarely shown to practice or devote any real attention to music, at all.
- Prone to Tears: Seldom does an appearance where he's involved end without him crying over something or other.
The oldest of the three Brightman brothers, and the arguable leader of the band.
- Chick Magnet: Once he and Ben broke up, he was suddenly very popular with the guys and literally held mass "sleepovers" at his house almost nightly just to take advantage of his newfound popularity.
- Nice Guy: The guy gets the crap smacked out of him by Bully, and then nearly body-checked off a boat by Jason, but he forgives all of this fairly readily with a smile and laugh when Jason attempts to apologize purely because the two are track teammates.
- Took a Level in Badass: After a Curb-Stomp Battle with Bully in which he was just barely saved by Jason, Brayden suddenly gained an excess of martial arts know-how- Which led to a case of Fanon Discontinuity when later discussions between the characters attempted to retcon it into Brayden having reluctantly beaten Bully up to save Peyton.
Ellington "Elle" Pierce
The middle Pierce sibling, who was held back a grade and is best known around school for her tendency to sleep around a lot.
- Retargeted Lust: The personality-based similarities between Travis and her ex-boyfriend Tony make is seem like her Friends with Benefits relationship with the former is essentially just using him as a replacement for the latter. Travis is entirely aware of this, and doesn't mind exploiting it.
The middle Brightman Brother.
- Dull Surprise: His trademark being that in contrast to his younger brother's emotional nature, he's been referred to as a zen master; Completely impossible to phase. He found out that his girlfriend (who, up to then, had only been with him as far as he'd known) recorded a sex tape with another guy in the time that they'd been together. His reaction? A mildly curious "is it hot?"
- Took a Level in Jerkass: After having convinced his girlfriend to keep their baby, and then proposed marriage to legitimize it, the two of them go to meet her parents. Moments after they disown her and Kaine himself is nearly strangled by her father, while she's openly weeping a couple feet away, he wonders aloud if they wouldn't be better off broken up so that he could potentially hang out with his brothers and play the field more.
A melodramatic senior who returns to Palm Beach High School after having been institutionalized for much of the previous year.
- Attempted Rape: On several occasions, he attempted to intimidate people into having sex with him, often physically. Just about every time, it backfired on him.
- Faux Affably Evil: He's generally very kind and overly-friendly toward guys he's attempting to seduce, but the affability ends as soon as he catches even the slightest hint of rejection, revealing his more sociopathic leanings.
- Informed Ability:
- He's supposedly a talented dancer who's headed to a prestigious performing arts school on a full-ride scholarship in spite of the fact that he's a heroin addict who attempts suicide once a week and is constantly in and out of the hospital with no apparent time to ever practice, or think about, dancing.
- He's routinely outsmarted by characters both highly intelligent (Travis and Bully) and average-to-slightly-dim (Lanie and Daniel) due to his transparent attempts at scheming, and easily outfought at one point by the equally-untrained, much smaller and less muscular Rockie.
- He claims that he can make any guy, regardless of sexuality, fall for him. This is repeatedly proven not to be the case.
- Remember the New Guy?
Algernon "Dinky" Dinkleberg
A birthday clown by trade, with a rather violent grudge against a certain Russian.
- Aborted Arc: His revenge plot against Bully was cut short because of a storm rendering his R Per's internet connection faulty and never picked back up.
- Almighty Janitor: Although he ultimately becomes the head of an international terrorist brotherhood of just about anything in facepaint, it's easy to forget that his day job is still being a clown that does children's birthday parties.
- Bigger on the Inside: His clown car fits a dozen clowns inside, with room for two more normal-sized people.
The owner and manager of Slendy's, a local diner back in Palm Beach.