Beware of spoilers from the previous game, The Crooked Man.
Sophie Grundler comes across as a model student at the Loren Catholic Academy, but her live isn't as perfect as it may seem. She's being bullied at school, and is often left alone at home because her father works long hours. As a result, she's been suffering from insomnia, and is often spacing out because of a lack of sleep.
When the whole world seems to have fallen asleep, Sophie is the only one that remains awake. She tries to find out what has happened and goes to check up on her friend and father, finding them awake, but in danger. She goes to rescue them, before learning that she needs to confront the Sandman about the world's state.
- Broken Ace: Sophie's a model student and never acts out of line, keeps a cool head, and comes across as mature because she's often alone at home and keeps the house running. Despite this she's being bullied at school, nobody is helping her with it, and she actually hates being home alone. She'd prefer for her father to leave his work more often and spend time with her, but she doesn't dare say anything.
- Be Careful What You Wish For: She wants to be able to sleep again. The dangers that Anne, Regan and Richard need saving from stem from her deepest, darkest wish of wanting them to be called out and punished for their behavior. Lullaby admits to causing this, as it would allow her to sleep again.
- Because You Were Nice to Me: The main reason she fell in love with David. He was the first person that made her feel comfortable to talk to about her problems, and he actually listened to her.
- Berserk Button: Don't Stay Up Late At Night reveals that you don't insult her red hair.
- Bonus Boss: She's the boss of the bonus scenario.
- Evil Costume Switch: Wears a sexy, black dress in Queen of the Night.
- FaceHeel Turn: Pulls one in Queen of the Night, gleefully watching the eternally sleeping world.
- Fate Worse than Death: Sleep With One Eye Open has Sophie return home and realize that the Sandman's death has fixed nothing. Time remains frozen, and Sophie is now the only person awake in an eternally sleeping world. Her insomnia gets worse due to paranoia and she begins to jump at shadows.
- Grew a Spine: Gets one in Don't Stay Up Late At Night.
- Heroic BSoD: Falls into a brief one when she fails to save her father.
- I Choose to Stay: Queen of the Night and Invisible Sweet Heart have her stay in the fairy world.
- I Want My Beloved to Be Happy: Gives up on David in Don't Stay Up Late At Night.
- Innocent Inaccurate: She understood that her mother was shot by 'Ban Crobber' as a child.
- It's All My Fault: Years ago, her father overstrained himself and suffered from stomach ulcers, which she blamed herself for and thought it happened because she was being selfish. Her aunt contributed to this idea by saying that her father would become better if she was a good girl and Sophie vowed to be that way, starting her stepford smiler tendencies.
- Leaning on the Fourth Wall: Don't Stay Up Late At Night has her flash a peace sign towards the camera. She's actually signaling it to the Sandman, who is watching from a telescope in his room.
- Missing Mom: Her mother was killed during a bank robbery years ago.
- My God, What Have I Done?: Her first reaction to accidentally killing the Sandman in Queen of the Night.
- Never My Fault: Chooses to blame all her problems on other people in Queen of the Night.
- No Sympathy: May react this way when reading the Sandman's diary, meaning the player is getting a bad ending.
- Pajama Clad Heroine: She was taken out of bed, leaving her to walk around in a nightgown.
- Parental Neglect: Her workaholic father is rarely home.
- "The Reason You Suck" Speech
- Tries to give Regan one in the mall and calling her a crybaby, but Regan just throws one back at her.
- Gives several in Don't Stay Up Late At Night.
- Red-Headed Heroine: Has noticeably bright, red hair.
- Stepford Smiler: Sophie is very passive about her problems, to the point of pretending that things aren't as big of a deal as they actually are because she's terrified that being honest about her feelings will cause trouble for others. Especially for her father.
- Strong Family Resemblance: According to a brief glimpse of Sophie's mother, they look very similar.
- The Tooth Hurts: She loses a tooth after being thrown from a burning building.
- Trademark Favorite Food: Ice cream. Her first ice cream was bought with money she got from the tooth fairy.
- Troubling Unchildlike Behavior: Downplayed. Flashbacks show that she looked down on crybabies, explicitly calling Regan one, even when they were upset over their parents constantly fighting. This attitude did contribute to later issues.
- Unrequited Love: She has a crush on David. Chooses to give up on him in Don't Stay Up Late At Night.
- Vomit Discretion Shot: If she eats the fairy food, the screen cuts to black before sounds of vomiting are heard.
- When She Smiles: She's described as having 'the smile of a goddess'.
- When You Coming Home, Dad?: Her father is usually at work, leaving her alone.
David Hoover was the protagonist of The Crooked Man and reappears in this game. After coming to terms with his issues in the previous game, things have gone better for him. He has moved out of his old apartment and his on-again relationship with his fiancée, Shirley, is going smoothly.
David got to know Sophie recently when bumping into her on the street. She felt comfortable in his presence and told him about her problems, with David listening to her. The two quickly struck up a friendship.
- Big Brother Instinct: He forms a brotherly bond with Sophie. He's willing to comfort Sophie and talk about her problems.
- The Confidant: His relationship with Sophie is based on this. She felt comfortable enough to tell him about her problems and considers him the only person she can talk to about things.
- Crash-Into Hello: David was walking down the street and staring at his phone, then proceeded to crash into Sophie, whose ice cream fell to the floor.
- Let's Split Up, Gang: David wants for them to stick together when the world is sleeping. Sophie insists on being okay on her own.
- Oblivious to Love. He doesn't know that Sophie has feelings for him. Possibly justified as Sophie may not have been open about her feelings for him.
- Previous Player-Character Cameo: He still plays an important role in this game.
- The Reveal: This David is actually an imposter. The real one is sleeping like everyone else.
The Shy Friend
Anne is Sophie's best friend in school. However, she is painfully shy and timid and can never stand up against Sophie's bullies. She feels horrible, because she cannot help her friend.
When the world falls asleep, Sophie checks up on Anne in the Academy's dorms.
- False Friend: The smirking ghosts in the Academy call her one and a liar.
- "The Reason You Suck" Speech: Sophie delivers one to her in Don't Stay Up Late At Night, demanding for her to either actually do something when Sophie gets bullied or to not apologize about not doing anything to begin with.
- Shrinking Violet: Her main personality trait.
- Timed Mission: Sophie must find her within 3 minutes in the academy.
The Petty Bully
Regan Blumberg comes from a rich family and her mother manages the Blumberg Mall. Regan relentlessly bullies Sophie while they are at school, usually by mocking her unnaturally bright, red hair.
Regan has to be rescued in the Blumberg Mall later on.
- Alpha Bitch: She is the main bully of Sophie.
- Backstabbing the Alpha Bitch: In Don't Stay Up Late At Night, Sophie fires back an insult at Regan's hair and the Girl Posse laughs at her.
- Firing Squad: She faces this fate, until Sophie saves her.
- Freudian Excuse: Her parents have been fighting for years.
- Girl Posse: Her two unnamed followers.
- "The Reason You Suck" Speech
- Gets one during the Blumberg Mall events, with Sophie calling her a useless crybaby that always waits for others to save her, rather than doing anything on her own. Regan retaliates physically.
- Gets another one during Don't Stay Up Late At Night, with Sophie telling her that she's going to face her problems and solve them, asking if Regan is going to do that, too, instead of using her as a stressball.
- Used to Be a Sweet Kid: With her mother and Regan being tormented by her abusive father for years really took its toll on her.
- We Used to Be Friends: She and Sophie. It's part of why Sophie puts up with her bullying so passively. She knows how bad Regan's homelife is.
The Absentee Father
Richard lost his wife when Sophie was very young and has been trying to raise her on his own since. Trying to give her a good life, he's taken to working long hours and has barely come home since.
Sophie searches for him at JP Gordon & Chase.
- Blood from the Mouth: His one screenshot shows him with it, indicating that his overworking himself has resulted in getting a stomach ulcer.
- Parents as People: Don't Stay Up Late At Night expands on his absence. Richard threw himself into work to cope with his wife's death and tried to give Sophie a good life, until the stress and work caused him to be hospitalized. As Sophie grew older and more withdrawn, he thought that she didn't want him around and worked longer to give her that freedom. Really, he just wants to be a part of his daughter's life.
- "The Reason You Suck" Speech: Sophie gives him one in Don't Stay Up Late At Night, yelling at him to think about why he - her father - is being called by the school about her.
- Workaholic: Richard is barely ever home and overall seems to ignore his daughter.
The Well-Meaning Imposter
Lullaby initially appears to Sophie in the form of David, to not only gain her trust and fulfill her inner wish of romance, but to also make sure that his personal lullaby for her will work on getting her to sleep.
After he is exposed, he takes Sophie to the Fairy World.
- Be Careful What You Wish For: Lullaby reveals that the dangers Anne, Regan and Richard were in are based on Sophie's dark, inner wish of her problems being taken care of in ways that would quickly solve them. Same with its appearing in David's form to her, appealing to her unrequited love for him.
- Empathic Shapeshifter: Lullaby's sole purpose is to make people fall asleep by appearing to them as whatever form they want it to be. Hence he looks like David to her and, later on, her mother.
- Loophole Abuse: Lullaby was created by the Sandman, so it cannot directly defy its creator. However, it was also created to fulfill people's wishes and was assigned to fulfill Sophie's wishes for now. He uses this to his advantage.
- Mr. Exposition: Plays this role in the Fairy World. He helps Sophie get there and is ready to read her the incomprehensible notes that she finds.
- Well-Intentioned Extremist: Lullaby's job is to help people fall asleep, especially if fulfilling their wishes makes it easier for them. But his way of fulfilling said wishes is extreme, to say the least.
The Insomniac Antagonist
The Sandman is a fairytale of an old man that sprinkles sand onto the humans' eyes and makes them fall asleep. When he tinkers around on creating Eternal Sleepsand, he gets the idea of using it and a time-stopping machine to force the entire world to sleep forever.
- Another Side, Another Story: He is the protagonist of the bonus scenario.
- Berserk Button: He goes absolutely nuts when he realizes that the Unicorn has Sophie's pink jewel.
- Eye Scream: According to an old fairytale, the Sandman scoops out the eyes of children that won't sleep.
- Genius Ditz: The Sandman studies the human world and can invent his own language, but either forgot or honestly didn't know that fairy food is poisonous to humans.
- High-Pressure Emotion: Twice.
- People kept waking up and forcing him to stay awake, the Sandman becomes so enraged and frustrated that he begins his initial plans of making the Eternal Sleepsand.
- Upon realizing that the Unicorn has Sophie's personal pink jewel, his face grew beyond red and he raced out of his home.
- MayDecember Romance: Wecome back, Insomnia reveals that the Sandman has actually fallen for Sophie, despite her being a human and him being a fairy that's centuries old.
- My God, What Have I Done?: His reaction in See You In A Bad Dream, when he realizes that he just forced Sophie into an endless nightmare. He even begins to cry.
- Nice Job Breaking It, Hero!: The bonus scenario shows that the meal the Sandman prepared for Sophie was a simple gesture of wanting to give her a nice meal, but forgetting that fairy food can kill humans. Same with him replacing the pink jewel with a pink-colored glass orb for the Unicorn, not realizing that the Unicorn was going to notice the difference.
- Not Evil, Just Misunderstood: The Sandman just wants to sleep himself again.
- Now, Where Was I Going Again?: His scenario allows him to consult in-game notes.
- Speaking Simlish: He speaks in an utterly incomprehensible language. Playing his scenario, it's revealed that this is what Sophie sounded like to him.
The Pranking Gadfly
A unicorn that appeared to Sophie. He doesn't seem well-liked by a lot of fairies, but has an apparently strong enmity with the Sandman. The Unicorn is forbidden from entering the Sandman's home and several traps are setup to help with that.
He agrees to help Sophie, in exchange of getting a pink jewel.
- Not Quite the Right Thing: His demand of a pink jewel from Sandman's home makes it appear like it's a pretty big deal of an item. If the player chooses to take the pink jewel back, they are locked into getting bad endings.
- The Prankster: He's a huge gadfly and nobody likes him because of that.
- Small Role, Big Impact
- Unicorn was the one to lead Sophie to the real, sleeping David and revealing Lullaby's true identity. This is what kicks off the second half of the game.
- Despite him being only important when it comes to getting a pink jewel for him, it's what the player chooses to do after this little quest that determines what ending paths they are set on.