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Haley Miller
- "You're talking to a Cali girl."
A San Francisco native, the new girl in Hillsdale and the POV character the reader makes all the decisions for. At the start of the series, she's described as "a fifteen-year-old girl of average height, average weight and a below-average sense of style".
- Affectionate Nickname: Reese calls her "Red" because of her hair. Most books have at least one ending where they become a couple.
- An interesting point - only once is Haley referred to by the usual abbreviation of her name "Hales". Most people don't shorten her name.
- Audience Surrogate: As common with any CYOA series, Haley is meant to be an ordinary teenage girl so readers can put themselves in her shoes and navigate each choice, from whether she takes the bus to school to if she goes to the high school dropout's Halloween party.
- Bratty Teenage Daughter: At her worst. Particularly in a "dead end" when she throws herself a sixteenth birthday party, letting her house get trashed and forgetting to invite her supposed best friends, and blaming her dad for not knowing the friend she sent her brother to stay with."It's my birthday. Or don't I get a day off from raising your kid for that?"
- Cool Big Sis: Sometimes to Mitchell. Her straining to act as a parent to him in the third book can lead to a dead end if the reader decides they are sick of looking after him all the time.
- Embarrassing Nickname: Her dad used to call her "Snoodles" when she was little and still does it when he's in a nostalgic mood.
- Forgotten Birthday: Haley turns sixteen on February 14th, and the only people who remember are her little brother and her grandmother. Subverted in chapters where she either has a birthday with cupcakes at the Hedon's band practice as a surprise party and one where the geeks bake her a cake and celebrate the day with her, as well as a dead end where she gets lots of birthday and Valentine cards, but her parents still forget and other versions have no one wishing her a happy birthday or sending her a valentine. One ending has her parents making up for it during spring break with am ice-cream cake, wishing her a "happy belated birthday".
- Granola Girl: Not necessarily one herself, but grows up this way due to her environmentally-conscious and health-conscious family.
- Naïve Everygirl: To the max, in order for the reader to put themselves in Haley's shoes and insert their own traits into her by making her decisions.
- Naïve Newcomer: Haley is new to Hillsdale, and everything she learns about it is just as new to the audience as it is to her.
- Series Continuity Error: The first book states that Haley is a Gemini. Later books retconned this as her birthday is confirmed to be Valentine's Day, which actually makes her an Aquarius, something explicitly stated in one of the endings in the fifth book.
- Significant Birth Date: Haley feels somewhat self-conscious about her birthday also being Valentine's Day.
- Significant Green-Eyed Redhead: Haley's eye colour is never mentioned, but she is the new girl that everyone is interested in and she has red hair.
- Single Woman Seeks Good Man: Unlike her friends, Haley's crushes are all nice guys. This is the main reason why the endings involving getting romantically involved with Matt don't work out.
- Spell My Name With An S: It's Haley, not Hayley or Hailey.
Coco De Clerq
- "Hello, and welcome to another day in the life of Coco De Clerq."
The self-proclaimed queen bee of Hillsdale High. Snobby, superior and extremely confident in herself, Coco lets nothing stand in the way of getting what she wants.
- A-Cup Angst: It's noted in the first book that Whitney is at least two cup sizes larger than her, and in another book, she acts jealous over Haley's growing chest.
- Aloof Dark-Haired Girl: Cynical, spoiled and untouchable, along with having dark hair (although apparently it's dyed from mouse to a richer shade).
- Alpha Bitch: A textbook example. However, the first book notes that Whitney and Sasha are both prettier than her.
- Break the Haughty: Getting drunk on New Year's Eve turns Coco from the most popular sophomore in school to lower than anyone else. Although she eventually claws her way back, books 3 and 4 makes life very hard for her. It's even worse in an ending when she sees all the footage Haley took of her and realizes what an awful person she is.
- Can't Hold Her Liquor: Coco only drinks one night a year. That makes it very easy for her to get drunk.
- Childhood Friends: With Whitney and Sasha, who she claims to have known "since birth".
- Clingy Jealous Girl: She spends the first two books chasing Reese and hating everyone he seems interested in. When she discovers Spencer is crushing on her, she turns this behaviour onto him.
- Dangerous 16th Birthday: One ending features Haley ruining Coco's sixteenth birthday, involving changing Coco's hair hightlights to be orange and red, cancelling the band and hiring a children's birthday clown and cancelling the white tiger performers and exchanging them for Vietnamese pigs. Coco's reaction isn't shown, but Haley videoes the whole incident and gives copies to everyone Coco's ever hurt.
- Heel–Face Turn: It looks like she's about to make one of these in books 3 and 4 (even getting tearful over how cruel immigration policies can be), but returns to her old behaviour by book 5.
- Lonely Rich Kid: Can come off this way in the books after Whitney resumes her friendship with Sasha and before she rejoins their friendship.
- Passionate Sports Girl: Very briefly in book 4 when she puts all her energy into playing tennis.
- Really 17 Years Old: Visits her sister in book 7 at college and attempts to pretend she's a student instead of a high-schooler.
- Rich Bitch: She lives in what is referred to as a Mc Mansion.
- Toxic Friend Influence: She constantly puts her friends down. It's clear that the way she's been treating Whitney has chipped away at her self-confidence and caused a lot of her body image issues.Whitney: I can't help the way my brain works.
Coco: That's assuming you have one, Whitney. - With Friends Like These...: All of Coco's friendships include her putting her friends down or mean tricks, including daring Haley to spy on Reese and then calling to tell him about it, and telling Haley that Cecily is trash-talking about her just to ruin their friendship.
Whitney Klein
- "That's nothing. The beadwork alone on this gown took me over twenty hours."
One of Coco's best friends and her loyal follower. However, despite copying Coco, Whitney is actually a rather sweet-natured girl in constant emotional turmoil. In later books, she starts making and selling her own line of clothes, and gains more confidence as a result.
- Attention Deficit... Ooh, Shiny!: Can jump from one subject to another quickly, forgetting all about the previous subject
- Best Friends-in-Law: With Sasha. They were originally friends, then Whitney and Coco dumped her, but when Whitney's mom and Sasha's dad became a couple, Whitney and Sasha returned to being friends. One ending of the fifth book involves Whitney crying because Sasha hasn't tried to talk to her, and the sixth book starts with them becoming friends.
- Beta Bitch: To Coco, most of the time. She gains her own voice as she grows more confident."You all look stunning and nothing Coco can say will make me change my mind."
- Brainless Beauty: Coco insists Whitney is this. She's not completely stupid, and her fashion sense and dressmaking talent is unmatched, but she isn't very smart.
- Dumb Blonde: The least intelligent of the popular girls.
- Embarrassing Nickname: Her dad calls her "Whittles", even in front of her friends.
- Evil Stepmother: Trish isn't yet married to Whitney's dad, but she's almost this, demanding attention and even steals Whitney's clothes. Whitney refers to her as her "stepmonster".
- The Fashionista: According to Coco, Whitney has turned shopping into a sport. Later on, she starts shoplifting clothes, and once she turns herself in and returns the clothes, she puts her energy into designing and making her own line of clothes, even selling them to mainstream stores and having a trunk show in one book.
- Heterosexual Life-Partners: With Coco for the first five books, and with Sasha from book six onwards.
- Informed Deformity: The first book says Whitney is dyslexic. This causes her no trouble in later books.
- Kindhearted Cat Lover: In the second book, Whitney won't let go of Cecily's cat at a sleepover and talks about how much she misses her pet cat, Princess Puffball.
- Likes Older Men: Is often seen to have crushes on older men, especially in early books. This includes one of her dad's business partners, the De Clerq's gardener and Haley's dad.
- Rich Bitch: Sometimes strays into this territory, especially when commenting the Miller fridge is similar to one in her garage.
- Weight Woe: Whitney is of average weight, but at the start of the series, she and Coco are called "No Eat And Repeat" in their attempt to be skinny. Whitney is implied to be bulimic, although this may be out of stress and Coco putting her down. This stops as soon as Whitney starts designing her own clothes and gains some confidence in herself. However, a "dead end" shows her becoming so stressed that her habits of vomiting to keep her weight down come back.
Sasha Lewis
- "Hey, speed racer, want to be my partner?"
A friendly, popular sporty girl with an amazing sense of style and a punk-rock edge.
- Best Friends-in-Law: Becomes this with Whitney, although they were friends before their parents began dating each other. Sasha is unsure about rekindling her friendship with Whitney in the fifth book, but they appear close at the start of the sixth book.
- Beta Bitch: Subverted. She is this to Coco, but compared to Whitney, is much less sycophantic, often nicer and has a life outside of being Coco's friend.
- Everyone Loves Blondes: Sasha is one of the most popular girls in school, and as Haley puts it in one book..."You're Sasha Lewis. What's not to love?"
- Heterosexual Life-Partners: With Whitney from the start of the sixth book. However, since Whitney's mom and Sasha's dad are engaged, their closeness acts as preparation for becoming stepsisters - however, their closeness is extremely genuine.
- High-School Sweethearts: With Johnny. They nearly break up just after being named "Best Couple" in sophomore year, but their friends manage to set them back up together.
- Lovable Alpha Bitch: When Coco is dethroned, she comes off in this way, including her own Girl Posse of Haley and Cecily. She's considered the main proof that being pretty, popular and rich doesn't mean you can't be a nice person.
- Missing Mom: Has one in the first book, who's away studying in Paris. She attempts to write to Sasha while she's away, but Sasha is too angry to read the letters. She eventually comes back and rebuilds her relationship with Sasha.
- Passionate Sports Girl: The star player of the soccer team. In book 5, she and Haley become co-captains of the team.
- We Used to Be Friends: For books 2 through 5, this is what happened between her and Coco and Whitney. Throughout book 5, Whitney shows signs of wanting to be friends with Sasha again, and the three of them reunite in book 7.
Cecily Watson
- "It's freezing out here! My native Hawaiian blood can't take it."
The head cheerleader at Hillsdale High, hails from Hawaii. Friendly, kind and well-liked by everyone.
- Nice Girl: The first time we see Cecily, one of her friends is telling her she'll be one of the homecoming sophomores, but states modestly that she probably won't even get nominated. In the second book, she is explicitly described as "one of the coolest, nicest girls in school".
Reese Highland
- "Well, Red, guess I'll see you around."
Haley's next-door neighbour and one of the cutest guys in Hillsdale. Later books introduce him as Haley's boyfriend, although the course the books take can change that.
- Embarrassing Middle Name: The first book reveals his middle name is Winstead. Haley wonders if this should dissuade her from wanting to date him.
- Nice Guy: Most of the time.
- The Teetotaler: Reese doesn't drink. Some of the others nickname him "Natural Highland" because of it.
Spencer Eton
A cute guy, knowing for hosting SIGMA, an illegal gambling ring for the high schoolers.
- Wild Teen Party: That's what SIGMA is meant to be.
Annie Armstrong
- "We need to get started on our next term paper."
A nerdy, rather clingy girl who is obsessed with getting good grades and considered low down on the popularity scale.
- The B Grade: Annie becomes extremely jealous when Haley gets the only A in the class for her essay, while she gets a B-.
- Can't Hold Her Liquor: She drinks a lot of Spanish wine at a dinner, and Haley has to bail her out.
- Clingy Jealous Girl: She's very aware of Dave's interest in Hannah Moss, and they almost break up, even though there is nothing going on between Dave and Hannah.
- Embarrassing Damp Sheets: The reason Coco started ruining Annie's birthday every year after they broke friends. Even worse, Annie and Coco were sharing a bed at the time.
- Give Geeks a Chance: One ending of the first book involves Haley setting Annie up with Dave. They date each other from the start of the second book and are heavily implied to have gotten particularly close after a night in Spain where Dave's cracking voice suddenly develops into an attractive baritone.
- We Used to Be Friends: With Coco. Annie claims they were best friends as kids until an incident at one of of their joint birthday sleepovers.
Sebastian Bodega
A suave Spanish student. He stays in Hillsdale for two years, joined in junior year by his ex-girlfriend, Mia Delgado.
- First Girl Wins: Haley soon realizes that she'll always be second best compared to his childhood sweetheart, Mia. One "dead end" has Haley attempting to give Sebastian a second chance, but spends the next few moments listening to Sebastian comparing her to Mia.
Hannah Moss
An advanced student in Haley's Spanish class, revealed to have skipped two grades.
- Child Prodigy: A thirteen-year-old in sophomore year. At the end of the year, she is still top of her class, despite being two years younger than all of them.
Alex Martin
An advanced student a year older than Haley, smart and often sweet, but also closed-minded and conservative.
- Belligerent Sexual Tension: Alex and Haley's relationship starts off this way in one storyline of the fifth book (there are two ways Haley can meet Alex, but the other one doesn't make them act this way).
Shaun Willkomen
- "Last one pulling water gets no banana mayo."
An artistic boy who expresses himself in strange ways, such as making eating a profession to get Irene to notice him, and talking backwards every so often.
- Class Clown: Shaun's eccentricity along with his outgoing personality make him this to a T.
- Nasal Trauma: At one point after Shaun's motorbike ride through a flaming heart, he's been told that he may have lost his sense of taste and smell forever. When he gets back to class, he declares that he can sense the smell of glue and that his bruised olfactory bulb is healing.
Devon Mc Knight
A cute guy who hangs out with the art crowd, often shy about expressing his feelings.
- Dogged Nice Guy: Exaggerated, bordering on yandere in book 7 when Haley pretends to ignore him. Returns to his normal personality when she starts being friendly.
- No Guy Wants to Be Chased: The reason Irene advises Haley to ignore him. A Dead End occurs when Haley attempts to be too nice and he goes from liking her to seeing her as a stalker.
