Kyle MasonThe game's protagonist, a kind and somewhat shy high school senior who is nonetheless popular at his new school. At his best friend Randy's behest, Kyle goes in search of a date to prom in hopes of getting over his last girlfriend.
- Clueless Chick Magnet: Comes off this way, since he seems to have been more or less oblivious to at least three different girls vying for his affections until Randy pressured him into finding a date.
- Color-Coded for Your Convenience: Kyle is associated with the colors black and grey.
- Cool Loser: Kyle is a bit dense at times, indecisive, and generally down on himself, but he's still quite popular, especially among girls.
- Deadpan Snarker: Mostly in his internal narration, but it's there.
- Determinator: By the time the plot really takes off Kyle will be willing to face death multiple times and confront a Physical God in order to bring her comeuppance for her actions.
- Forced to Watch: This is why Claire doesn't kill Kyle; she was ordered to leave Kyle alive so that Kyle can suffer psychologically instead, by being forced to watch his prom dates being gruesomely murdered right in front of him.
- My Greatest Failure: The circumstances that ended his last relationship, when Kyle was so overcome at the sight of Serena's injuries that he couldn't bear to stay in the same room as her and ended up not being there for her in her last moments.
- Nice Guy: One of the traits that people most commonly cite as a reason for his popularity. In fact, it's necessary to do good deeds and help people out throughout the game if you want to get the best ending.
- Second Love: What he's looking for.
- Shut Up, Hannibal!: Each time Kyle learns more about Dolores's miserable life, he sympathizes with what she went through but firmly insists that it doesn't justify committing murder.
- Thou Shalt Not Kill: Kyle firmly believes that no matter what, nothing could possibly excuse murdering people. So when Kyle learns that Dolores is murdering people because they wronged her, Kyle expresses sympathy but firmly believes that regardless of what Neela, Maggie, and Brooke did, that doesn't make it acceptable to kill them over it. In fact, if you betray Kyle's ideals and kill the mirror world Serena when given the chance, it nets you a Non-Standard Game Over and gets Kyle killed.
- Unwitting Pawn: To both Brooke and Dolores. First, he is unknowingly the center of Brooke's plot to humiliate Dolores and afterwards, Dolores uses him to lead each of the love interests to their deaths.
Randy GoodwinKyle's best friend at St. Giles Academy. Randy is the one who starts Kyle on his quest to find a prom date, hoping to help him move on from his last relationship. Though Randy is a major character, it's possible that the real Randy will never appear at all in your playthrough, depending on which ending you get.
- Black and Nerdy: Downplayed.
- Black Best Friend
- Color-Coded for Your Convenience: Randy is associated with the color orange.
- Exposition Fairy: Randy kicks off the plot by planning to get Kyle a prom date and pushing him to talk to the available girls. He uses his role as a member of the yearbook team to gather notes on his fellow classmates, which Kyle can view for hints on how to win over a love interest. He's also the one to drop information about Kyle's ex for the player's benefit.
- False Friend: The Mirror Randy copies the actions of the real one throughout the time loop, but only at the Big Bad's behest. He doesn't care about Kyle at all, and seems to express amusement at the idea of Kyle's suffering.
- Manly Tears: In the best ending, Randy sheds them when Kyle finally wakes up in the hospital.
- The Mole: Randy, or at least the version existing in Dolores's fabricated world. The actual Randy has nothing to do with it. Even the Developer's Room states that "Randy did nothing wrong".
- Scary Shiny Glasses: One of his character portraits has him with these. It's actually only the Mirror Randy who has them, as a clue that he doesn't have your best interests at heart.
- Unwitting Instigator of Doom: Arguably the real Randy, who did push Kyle to ask a girl to prom and ended up helping set him up with one of the three girls, thus inadvertently helping to snub Dolores.
Neela DevarThe first of Kyle's potential love interests, a sweet and bubbly girl from the junior class. Neela is known for her warm, friendly personality and her cooking skills.
Neela is deemed "The Liar" by the Big Bad for her role in convincing Dolores that Kyle wanted to ask her to prom and is killed for it once Kyle takes her.
- Apologizes a Lot: During her prom night, when Claire reminds Neela of the lie she once told, Neela keeps apologizing for it—and she keeps apologizing even after Claire has already cut out her tongue.
- Color-Coded for Your Convenience: Neela is associated with the color blue.
- Crash-Into Hello: She is introduced by running straight into Kyle while rushing to class because she is late.
- Foreshadowing: While Neela and Kyle are eating lunch together, if you're on the 2nd loop, Neela will ask Kyle if it's okay to keep secrets. When Kyle responds that it's okay to keep minor secrets but secrets that could hurt people should probably be told, Neela then asks about the possibility that telling the secret would hurt people just as much. It later turns out the "secret" Neela is keeping is that she helped Brooke in a prank by lying to Dolores, but only because Brooke blackmailed Neela into it by threatening to reveal to the press that Neela's father has mafia ties.
- Girlish Pigtails: Neela wears her hair this way, reflecting her innocent personality.
- Hope Spot: If Neela is the third girl Kyle takes to prom, she makes preparations to face Claire in advance, bringing with her a pendant for devotees of the goddess Durga and reciting the mantra Om Dum Durgayei Namaha. Since this is a way to ward off evil in the Hindu faith, it looks like Neela might survive after all...and as Claire notes, this would have worked in any other context, but since they're currently in an alternate dimension, holy defenses are null and void, and Claire breaks the pendant and kills Neela anyway.
- Leitmotif: "Sugar and Spice".
- Meganekko: She wears large circular glasses.
- My God, What Have I Done?: Her immediate reaction to lying to Dolores about Kyle, and only worsened when she sees how brutally Brooke treats Dolores. She is so remorseful that when you talk to her in the Developer's Room after getting the best ending, she is initially fearful that she has been sent to hell for her actions.
- Nice Girl: Neela is popular among other students in-universe for being kind and friendly, and Kyle muses to himself that he finds Neela to be a very "warm" person; Neela even personally makes Kyle a homecooked meal when they have lunch together. This is seemingly subverted when you later learn that Neela lied to Dolores about Kyle being interested in her, helping to set up Brooke's prank—and then double subverted when it turns out Brooke blackmailed Neela into telling that lie; Neela immediately felt extremely remorseful upon her misdeed, and was even going to help Dolores up and apologize after the prank before Maggie advised against it. In fact, during Brooke's "after-party", Neela had a sudden attack of conscience and was going to confess the whole scheme to Kyle before Dolores's revenge scheme interrupted everyone by pulling them into the nightmare world. So Neela ultimately still turns out to be a nice girl after all.
- Stepford Smiler: Has shades of Type 1 due to her father's mafia ties, which if revealed would tear her family apart because he would go on the run. Brooke uses this against her to get her to lie to Dolores.
- Supreme Chef: Neela is known throughout the school for her cooking skills, and she plans on attending culinary school and someday opening her own restaurant.
- Tongue Trauma: The punishment delivered to her by Claire before she is killed.
- Trademark Favorite Food: Strawberries, which you can use as part of Kyle's prom proposal.
Maggie PhamThe second girl that Kyle meets, a tomboyish and athletic basketball star. Though she is brash and temperamental, she has a soft side and secretly loves cute things.
Maggie is labeled "The Forger", due to her creation of a fake social media post in Kyle's name to convince Dolores that he wanted to ask her to prom. She is likewise killed once Kyle chooses her.
- An Arm and a Leg: Her torture at Claire's hands before she is killed is having her hands and then her arms cut off.
- Color-Coded for Your Convenience: Maggie as associated with the color red.
- Cuteness Proximity: She secretly loves cute things and stuffed animals, and if you choose to ask her to prom, Kyle wins her over with a teddy bear.
- Dumb Jock: The developer's notes state that Maggie was meant to have some shades of this so that she wouldn't be just a classic Tsundere. It's why she had to get Brooke to forge her SAT scores, in turn giving Brooke leverage to rope Maggie into helping her torment Dolores.
- Even Tsunderes Have Standards: Maggie was blackmailed into helping with Brooke's prank by setting up a fake social media page supposedly from Kyle, and initially Maggie is willing to hurt Dolores because at least her own future goals will be safe. But Maggie doesn't enjoy doing it, and Maggie becomes furious when Brooke escalates the prank into outright beating up Dolores; Maggie accuses this of being low even for Brooke. Finally, after Neela has a sudden attack of conscience during Brooke's "after-party" and tries to confess the whole scheme to Kyle, Maggie decides she agrees with Neela that the scheme went too far, and also tries to confess before they're interrupted by being pulled into the nightmare world.
- Foreshadowing: While Kyle and Maggie are hanging out by turning picking up trash into a mock basketball game, if you're on the 2nd loop, Maggie unexpectedly turns serious and asks Kyle if he has a dream important enough that he would be willing to lie, cheat, or steal to make it happen. Maggie passes this off as just messing with Kyle, but in reality, this is because Maggie is still feeling guilty over having created a fake social media page to help Brooke trick Dolores because Brooke threatened to expose Maggie's fake SAT scores if Maggie didn't help, which would jeopardize Maggie's future basketball career.
- Fun with Acronyms: Her full name is Margaret Vinh Pham. MVP.
- Girls Love Stuffed Animals: Maggie publicly denies this to keep up her tough reputation, but Maggie is fond of collecting cute stuffed animals, and Kyle can earn Maggie's affection by giving her a teddy bear.
- Hope Spot: If Maggie is the third girl Kyle takes to prom, she makes preparations to face Claire in advance, bringing with her a coin that her grandfather supercharged with Taoist rituals. Since this coin is a talisman to ward off evil spirits and actually saved her grandfather's life in Vietnam, it looks like Maggie might survive after all...and as Claire notes, this would have worked in any other context, but since they're currently in an alternate dimension, holy defenses are null and void, and Claire breaks the coin and kills Maggie anyway.
- Leitmotif: "Most Valuable Player".
- Sore Loser: She challenges Kyle to a basket shooting competition if you go on her lunch date. Depending on your dialogue choices, she will either get flustered and miss her shot, getting mad when Kyle wins, or she will yell at Kyle to distract him during his final shot so that she wins and will subsequently gloat. If you speak to her at prom after choosing one of the other girls, she will react coldly and state that Kyle has bad taste in women.
- Tomboy with a Girly Streak: Tries to deny any of her girly traits, but by her own admission is a sucker for cute stuffed animals... and cute boys.
- Tsundere: Acts tough and brash, and she'll get mad if Kyle says something to fluster her, but she can be sweet underneath it all.
Brooke O'KeefeKyle's third potential love interest, a smart, beautiful, and popular girl who also happens to be a senator's daughter. Even Kyle thinks she is out of his league, but Brooke seems interested in him despite her cool outward demeanor.
Brooke is deemed "The Mastermind" for being the one to orchestrate Dolores's humiliation. Like the other two girls, she is killed for her actions when Kyle takes her to prom.
- Alpha Bitch / Academic Alpha Bitch: She comes off this way initially, though she starts to seem more like a Lovable Alpha Bitch if Kyle pursues her. She isn't. She's much, much worse.
- Ambition Is Evil: Her entire motivation for ruining Dolores's life is because she wants the valedictorian spot so that she can get into Yale.
- Color-Coded for Your Convenience: Brooke is associated with the color green.
- Evil Redhead: She deliberately tries to make Dolores either drop out of school or kill herself, all so Brooke can have Dolores's valedictorian spot and thus be able to make it into Yale.
- Eye Scream: Brooke gets stabbed through the eye and lobotomized before she is killed by Claire.
- Foreshadowing: While Brooke is helping Kyle with his paper on Shakespeare's famous play Hamlet, if you're on the 2nd loop, Brooke offers a cold and harsh interpretation of Ophelia's character, accusing Ophelia of being a frail, maudlin little girl allowing her self-worth to be determined by other people. This foreshadows the later revelation that Brooke is ambitious to the point of remorselessness, leading to her extremely cold-blooded treatment of Dolores and refusal to apologize for it.
- Hope Spot: If Brooke is the third girl Kyle takes to prom, she makes preparations to face Claire in advance, bringing with her a crucifix and reciting a prayer to Saint Michael the Archangel. Since in the Catholic faith, this is a prayer specifically for defense against rulers of darkness and spirits of evil, it looks like Brooke might survive after all...and as Claire notes, this would have worked in any other context, but since they're currently in an alternate dimension, holy defenses are null and void, and Claire breaks the crucifix and kills Brooke anyway.
- Karmic Death: Even more so than the other two girls, as the point of lobotomizing Brooke before killing her was to destroy what she considered her best trait: her mind.
- Leitmotif: "Elegant Ambition".
- The Resenter: It turns out that Brooke is angry with her senator father for gambling away her college fund, severely damaging her chances of attending Yale. And that's nothing compared to how much she resents Dolores for beating her in class ranking.
- Significant Green-Eyed Redhead: In a positive sense, she's one of Kyle's three potential prom dates and thus very significant. In a negative sense, she was the mastermind of a very cruel prank that finally caused Dolores to snap and begin her revenge scheme, so Brooke is very significant to the overall storyline.
- Teens Are Monsters: Brooke blackmails her classmates into ruining the life of a girl who never wronged her, outright states that she hopes Dolores kills herself, and physically brutalizes Dolores after humiliating her... all because she wants to be valedictorian. And afterwards, she has the gall to say that she's done nothing wrong.
ClaireA New Transfer Student at St. Giles Academy. She seems calm, polite, and helpful, but there's something a little off about her.
Claire is actually a familiar, a construct of magic created by the Big Bad and ordered to carry out punishment on those who wronged her.
- Affably Evil: Claire is cheerful and polite towards Kyle, even after she's shown her true colors by killing Neela, Maggie, and Brooke. She even commends Kyle for his bravery and kindness and gives him permission to close his eyes as she "eliminates" herself.
- Color-Coded for Your Convenience: Claire is associated with the color purple.
- Dissonant Serenity: Randy's notes on Claire state that no one has ever seen her get angry. She is even calm when brutally murdering someone. This is because she can't experience emotion, though.
- The Dragon
- New Transfer Student: She introduces herself as a student who just moved to St. Giles from abroad.
- Knight of Cerebus: Her appearance is the first hint that things at St. Giles aren't all that they seem.
- Leitmotif: "Servant's Heart". Reprised during the prom scenes as "My Mistress's Will" and again at her own death as "A Role Ended".
- The Soulless
- Stepford Smiler: A Type 2; as a magical construct, she can't experience real human emotion and has no free will of her own.
- You Have Outlived Your Usefulness: Declares this about herself once she has killed all three of the girls and delivered Kyle to Dolores. She ends her own life after explaining her role to Kyle and shows no regret about having to do so.
The valedictorian of St. Giles Academy's senior class, a quiet and reserved girl confined to a wheelchair due to cerebral palsy. Dolores was the victim of a cruel Prank Date set up by Brooke, who along with Neela and Maggie led her to believe that Kyle wanted to ask her to prom, in order to humiliate her. Brooke's treatment finally caused Dolores to snap and unleash the magical powers inherent to her family so that she could make Kyle and the girls suffer.
- A God Am I: Eventually reaches this point, since her powers grow stronger with every life she takes and nobody can challenge her on even footing within her mirror world.
- Big Bad: While Claire is the one who kills Kyle's prom dates, Claire is only a familiar acting on behalf of Dolores, who hatched the entire plot as a way of getting back at those who wronged her.
- Color-Coded for Your Convenience: Dolores is associated with the colors pink and white.
- Despair Event Horizon: Crosses it after seeing her dream of being loved destroyed and facing Brooke's torment.
- Disabled Means Helpless: Dolores hates being treated this way, feeling belittled by it.
- Disabled Snarker: She demeans and belittles Kyle with sarcastic commentary whenever the player receives a game over as well as during their final confrontation.
- Disappeared Dad: Her father abandoned her and her mother after Dolores was born, not wanting to have to raise a disabled child.
- Disproportionate Retribution: Not so much her treatment of Brooke, given Brooke's open cruelty, but Dolores's treatment of Neela and Maggie definitely counts as this trope; while Neela and Maggie did help Brooke's prank by lying and creating a fake social media page, respectively, those are relatively minor offenses compared to Dolores murdering them over it (and on top of that, Brooke blackmailed them into helping in the first place).
- Evil Feels Good: She is obviously reveling in finally having power over others, and when you talk to her in the Developer's Room she even admits that she had fun being a villain.
- I Just Want to Be Loved: Outright stated. Dolores just wanted someone to show her love and affection that she felt she had been denied due to her disability. Once she was convinced she could never have that, she went off the deep end.
- Ill Girl: Born with cerebral palsy and confined to a wheelchair due to it.
- In Love with Love: As Dolores admits, even to herself it isn't clear whether she was actually attracted to Kyle, or whether she was more attracted to the idea of having a loved one to accept her and take her pain away.
- Irony: If Dolores hadn't committed her magical revenge scheme, she actually might have achieved her dream after all—because Neela and Maggie were about to spill the beans on Brooke's prank at the after-party, and Kyle looked like he was about to confront Brooke, so Brooke might have faced the consequences of her misbehavior anyway, and Kyle might've helped Dolores.
- Leitmotif: "A Dying Dream", reprised as "Queen of Broken Hearts" and "The Dream is Dead, Long Live the Dream".
- Misplaced Retribution: Dolores forces Kyle to watch his prom dates being murdered in front of him and traps him in a time loop because she thinks he's a "heartbreaker" who toys with women, as Kyle showed up to the prom with a different date. But Kyle had absolutely no idea that Dolores thought she was going to have a date with him, as he wasn't present for Neela lying and Maggie creating a fake social media page, so Dolores is punishing an innocent person because he was used for a prank he didn't even know existed.
- Slasher Smile: Most images of her besides her sprite and character portrait show her only in silhouette, with a wide grin.
- Trauma Conga Line: Born with an illness which severely restricts her mobility, her father left the family over it, her loving mother died leaving her with an aunt who treated Dolores like she was helpless and dismissed her feelings, bullied and ignored by her peers, and then she was tricked into thinking that a boy she liked wanted to ask her out, and was beat up and told she was better off dead by the girl who orchestrated it all. No wonder she snapped.
- Walking Spoiler: Considering that you can reach the final act of the game before even realizing she's there, yeah.
- Walking the Earth: Her fate in the best ending.
- Woobie, Destroyer of Worlds: After having a very miserable life so far, Brooke's cruel prank on Dolores was the straw that broke the camel's back, motivating Dolores's revenge plot.
- Yandere: Generally averted, as she is trying to make Kyle suffer rather than keep him all to herself. Played straight in the bad ending, though.
Eleanor RothDolores's deceased mother, who like her daughter made a deal with the demon Moloch in order to gain magic power and life after death. Unlike Dolores, Eleanor's motivation was only to watch over and protect her daughter, but she was unable to reach Dolores enough to prevent her actions. She appears in order to help Kyle in the game's best ending.
- Adult Fear: Seeing your child lonely, bullied, and eventually pushed over the edge and turning to hatred and hurting others, all while being unable to do anything about it.
- Color-Coded for Your Convenience: Eleanor is associated with the colors white and gold.
- Driven to Suicide: Killed herself rather than letting cancer take her so that she could gain powers from Moloch and watch over Dolores.
- Leitmotif: "A Mother's Tears".
- Light Is Good: Despite having made a pact with a demon, Eleanor uses her powers to help and protect, and dresses in all white.
- Love Redeems: In the best ending, reminding Dolores of her mother's love via a poem that Eleanor wrote her is what convinces Dolores to let Kyle go and try to make up for her actions. In fact, the creator comments in the Developer Room that the character of Dolores's mother was created to make a happy ending possible, as Dolores couldn't be redeemed by any love from Kyle because that would accidentally be rewarding Dolores for her actions, so Eleanor is the one who redeems Dolores instead.
- Morality Chain: To Dolores. Eleanor is the one to pull her back from the edge and convince her to try and forgive Kyle in the best ending, and she promises to stay by Dolores's side to help her eventually redeem herself.
- Walking the Earth: In the best ending, along with Dolores, as neither can enter heaven or hell since they gave up their humanity in their pact with Moloch.
- Walking Spoiler: Even more of a walking spoiler than Dolores, as you may not even meet Eleanor unless you've been diligent about collecting the "mother's poem" pages.
- Woman in White: Eleanor dresses in a white shawl symbolizing hope, which especially stands out during the fourth and final time loop as the rest of the school has become a bloody, dark wasteland.
Serena GutierrezKyle's ex-girlfriend, whom he is still hung up on a year after their relationship ended. Serena died after being badly injured in a car wreck, and Kyle's guilt stems from the fact that he couldn't bring himself to be with her in her last moments. A false representation of her appears in the mirror world, but the real Serena only appears in flashbacks.
- All There in the Manual: Her character portrait, surname, and the full details on what exactly happened with her are revealed in the Developer's Room notes after obtaining the best ending.
- Hell Is That Noise: Mirror Serena's scream.
- Leitmotif: "Dear Serena".
- The Lost Lenore: Kyle still feels guilty about her death and his own behavior in the moments leading up to it.
- Posthumous Character: Serena is dead before the story of Prom Dreams begins, but she is a major motivating factor in Kyle's behavior, as her death is the reason Kyle is initially reluctant to date again.
- Red Herring: As you get more information about Serena and how her relationship with Kyle ended, it starts to seem like she might be the one behind the strange happenings at St. Giles. She actually has nothing to do with it besides a construct of her appearing in the mirror world.
- Talking the Monster to Death: How Kyle finally defeats the mirror image of Serena which pursues and tries to kill him: admitting his guilt over abandoning her and asking forgiveness.
Annie HorowitzA girl who attended St. Giles Academy around ten years ago, who was murdered by a classmate after he asked her out and she turned him down. Annie's story reappears several times throughout the game, hinting that she has some kind of significance to the strange goings-on at the school.
- If I Can't Have You...: The motivation for her murder.
- Posthumous Character
- Red Herring: Annie's story and the idea of people dying before or during prom because of being snubbed in love are repeated throughout the game, suggesting that Annie or someone connected to her might have something to do with the plot. She doesn't, really. Her story is mainly to foreshadow the unrequited love motivation for the Big Bad and to add creepiness to the seemingly idyllic school.