Because the plot is based on Jennifer's memories alone, what really happened is not always obvious to the player due to the fact that Jennifer's memory can alter or distort events and dates. The fact that the plot is only based on Jennifer's point of view also stops the player from seeing all sides of the story as well. What happened before and after the events of the game is never revealed, although many hints are given. The player must "connect the dots" and infer the story through dialogue, memos, notes, visual cues, etc.
Jennifer's parents rode a luxury airship traveling from Cardington to India. The airship crashed and Jennifer was the sole survivor.
After the airship crashed, a poor pea farmer named Gregory M. Wilson found and rescued Jennifer. His son Joshua had either disappeared or died, and he was mentally unstable as a result. Gregory was depressed, suicidal and alcoholic. It is possible that he had something to do with the kidnapped children mentioned in the game, but other evidence suggests he may have just used the kidnappings as inspiration for one of his stories. Gregory took Jennifer in and was kind to her, but he dressed her up like his son and called her his son's name. While Gregory was kind to Jennifer, she knew he was not mentally stable. He had a gun he often seemed to want to use on himself, drank heavily, and refused to let her leave.
One day, a young girl from the nearby orphanage named Wendy discovered Jennifer in Gregory's basement through a window, but thought she was a boy and referred to her as a Prince. They started to exchange letters, and though Jennifer revealed her gender, she continued to be the Prince, with Wendy being the Princess.
Jennifer eventually fled from Gregory with Wendy to the orphanage where she became involved with the Red Crayon Aristocrat Club, a club secretly run by Wendy as the leader. Wendy and Jennifer became best friends and Jennifer even tolerated the games she didn't quite agree with. However, Wendy became very attached to Jennifer and this could be interpreted as her falling in love with Jennifer. Although this wouldn't normally be a problem, Jennifer found a small puppy. She named him Brown and gave him a collar. She even showed it to Wendy, though Wendy preferred that it be just her and Jennifer forever. Jennifer resisted this however and kept Brown, eventually favoring him over Wendy.
Eventually, Hoffman mysterious disappeared, along with Martha Carol and Clara, leaving the children all by themselves. Hoffman wrote in his diary, "I'm leaving the orphanage. Clara's here to look after things, and the children are quickly growing up. I've done right and fulfilled my duty. Bloody hell! All the trouble started when that wretched child arrived... I've done nothing to deserve this!"
Wendy became jealous and began spreading lies about Jennifer to punish her, commanding the aristocrats to bully her in several ways. Jennifer still resisted Wendy and this eventually lead to the children kidnapping and killing Brown. Jennifer snapped and slapped Wendy, setting the orphanage children straight. They dethroned Wendy as the Princess of the Red Rose and elected Jennifer as the new one.
After Wendy was overthrown by Jennifer who had finally realized her friend's cruelty, Wendy ran off. She started dressing up like Joshua and manipulating Gregory, training him like a dog. Gregory had become "Stray Dog". One rainy night in December, she brought him to the orphanage and he killed everyone. Jennifer was the only survivor yet again, and was escorted from the crime scene by an officer named Anthony Dolittle. The tragic murder of all the residents of a rural orphanage were instantly bumped from the front cover of the daily newspaper to an obscure corner.
Jennifer loses her memories after this incident, and at some later point in time, when she is 19 years old, she revisits the orphanage in her mind to remember her forgotten past. How Jennifer's life goes on from here is unknown and how her life was before the airship crashed is also an enigma.
March 1930 - The Little Princess
In the dead of night, Jennifer sleeps at the back of a bus traveling along a rural country road. At the front of the bus, a young boy sits, reading a handmade storybook. He awakens her and begs her to read the rest of story to him. Jennifer takes the book, but to her surprise, most of the pages are blank. The bus comes to a stop and the boy suddenly runs out of the bus and down the road. Jennifer yells for him to wait, and follows the boy off the bus which, immediately after, speeds away, leaving Jennifer all by herself.
Following the path after the boy up a strange hill, Jennifer hears familiar sounds of a dog barking. She finds an unlocked shed and enters it, only to find a dog collar bearing the name Brown. After leaving the shed, the boy is again spotted, running away.
Following the boy, Jennifer is led to an orphanage known as the Rose Garden Orphanage. Through the bars of the front gate, she sees two girls wearing paper bags over their heads, with one of them beating something in a sack with a stick. Behind them, the boy enters the mansion, shutting the door behind him. Frightened, Jennifer looks for a different way in. She finds a back gate and at the front of the orphanage, she finds that the girls and the sack have disappeared. Jennifer enters the orphanage and the front doors lock behind her. Following the boy up the stairs and into the attic, she finds the boy standing on top of a fort, and he tells her to read the storybook to him. Jennifer opens the book and she discovers that the story has more to it.
A voice calls out over a loudspeaker, announcing the start of a funeral. The boy advises Jennifer that the funeral is for her "dear friend" before disappearing again. In the inner court of the orphanage, Jennifer finds a grave and senses that something important to her buried there. Digging furiously, Jennifer finds a coffin and peeks inside, discovering the beaten sack from before. Before Jennifer can take a closer look however, the girls wearing paper bags surround her. One exclaims how filthy Jennifer is, giving the girls a cue to pour water on her ceremoniously. A voice over a loudspeaker intercom system then gives a pre-flight speech, and Jennifer is helplessly pushed into the coffin as the group of girls shut her inside, and carry her away into the darkness.
April 1930 - The Unlucky Clover Field
Jennifer wakes up and finds herself tied with rope to a support beam in a strange room. Over a loudspeaker, the boy, watching her from the next room, tells Jennifer in a cruel, mocking tone, that she has been a bad girl. He advises her that every month, Jennifer must offer a gift to the Red Crayon Aristocrat Club or he, the ruling Prince, will kill her. The boy then lowers a pair of scissors on a pulley and cuts Jennifer free. Exploring the area, Jennifer finds the door to the Aristocrat Club with a poster on it stating that the monthly gift is a beautiful butterfly.
After looking out of some windows, Jennifer discovers that she is traveling on an airship in the sky. Jennifer explores the airship and meets many girls, who are addressed as princesses; most of them are fairly rude to her. Jennifer learns their names: Diana, Meg, Eleanor, Susan, Olivia, Amanda, and Clara. One girl, however, addresses herself as Wendy and greets Jennifer in a polite and friendly manner. She also meets a few boys: Xavier, Nicholas, and Thomas and two adults: Hoffman and Martha Carol. Jennifer soon frees a dog bound by rope with scissors, and realizes from the dog collar she saw in the shed that his name is Brown. The two bond, and Brown follows Jennifer throughout the airship.
Jennifer locates a green butterfly, but when she attempts to put it into the monthly gift box, it is refused and called "ugly". Jennifer eventually finds a beautiful blue butterfly, and soon after, many monsters known as Imps swarm her. Jennifer, escaping the Imps, makes her way to the monthly gift box. It accepts the butterfly, and inside the Club Room, Diana throws Jennifer onto the ground and states that her butterfly is "worth nothing". As punishment, Diana and the rest of the Aristocrats encourage Amanda to poke a stick with a rat tied onto it onto Jennifer's face, and she faints.
May 1930 - Sir Peter
Jennifer wakes up in the Filth Room and finds a letter from Amanda, telling her to meet her at the highest point of the airship. On the airship's roof, Amanda apologizes to her, begging for forgiveness from the rat punishment.
Back in the airship, Jennifer is called by the Aristocrat Club to find Wendy's missing pet rabbit, Peter. Jennifer begins her search and upon entering the Filth Room, Jennifer encounters a mysterious man who simply ignores her and walks away. Jennifer then finds Peter, but the rabbit runs away and Jennifer gives chase. With Brown's help, Jennifer is led to a bloodied bag being beaten by Imps; they notice her and alert Hoffman. Hoffman suddenly attacks Jennifer, and Jennifer has no choice but to kill him. After Hoffman's defeat, the Imps drag his corpse away.
Jennifer carries the bloodied bag to the monthly gift box, and Peter scurries out of the bag and into the Aristocrat's room. Inside, Jennifer is promoted and Amanda is demoted by the Aristocrats. The Aristocrats repeat the rat punishment with Jennifer giving the punishment to Amanda this time. Upon putting the rat in Amanda's face, she immediately faints and looking at the rat herself, Jennifer realizes it is covered in maggots and faints as well.
Jennifer comes to in the Club Room as the boy watches her from on top of his fort. He offers her three storybooks: The Bird of Happiness, Mermaid Princess and The Goat Sisters, in order to make her remember her "sin".
July 1930 - The Bird of Happiness
This chapter begins with Jennifer awakening in a room with Eleanor. Jennifer realizes Eleanor's bird cage is empty, and Eleanor leaves.
Leaving the room, Jennifer overhears Diana and Meg talking about Eleanor, and they walk away, dropping a red feather behind which Jennifer takes. Jennifer takes a look at the monthly gift which is the "Bird of Happiness".
Using the red feather as a clue, Brown assists Jennifer in finding the bird's scent and Jennifer finds a path of red feathers leading to the women's lavatory; inside one of the stalls is a bird drawing with blood above it. Hearing someone approaching towards her, Jennifer hides in the stall and Diana and Meg enter giggling. Jennifer hears Diana and Meg snickering and laughing as they mock Eleanor. They leave, but Jennifer is soon caught eavesdropping on Diana and Meg.
Meg reveals to Jennifer that the Bird of Happiness is somewhere in a room nearby and that it will die if it isn't found in time. Meg also tells her that she cannot remember which room it was. Diana and Meg then make a bet to see if Eleanor would cry or get angry upon finding her dead bird.
Jennifer finds a box in one of the rooms. After a long search and using various clues, Jennifer realizes that each box only contains a smaller box inside of it. Eventually, when Jennifer opens the last box, she finds that Eleanor's bird has indeed suffocated and died.
Eleanor stumbles into the room, takes her bird's corpse from Jennifer's hands, and merely places its limp body into her cage. Eleanor then apathetically donates it to the Aristocrat Club's gift box. Meg and Diana follow after Eleanor, leaving Jennifer behind.
Jennifer remembers a part of her promise by the chapter's end: "everlasting happiness is a joke."
August 1930 - The Mermaid Princess
This chapter begins with Jennifer awakening in a room with Diana, who notices Hoffman's fish is gone. Diana then leaves Jennifer alone to search for the missing fish.
Jennifer notices Olivia crying at the monthly gift box. Upon examining it, Jennifer realizes that the monthly gift is an 'unmarried mermaid'. Jennifer meets with Meg and Eleanor who are discussing the existence of mermaids. They ask Jennifer about mermaids and leave, leaving a fish scale behind. Using the scent of the fish scale, Brown leads Jennifer to a fish head, and using the scent of the fish head, to a room on the other side of the airship. Along the way, Jennifer sees Clara with Hoffman and Diana searching for Hoffman's fish.
In the room with the fish scent, Jennifer fights the Mermaid Princess. After its defeat, the monster turns into a mermaid doll and Jennifer finds herself in Hoffman's room with Diana and Hoffman. Hoffman strokes Diana's head and body in a sexual manner as she sobs and he leaves. Diana grabs the mermaid doll, lashes out at Jennifer, and places a dirty rag from inside of Hoffman's aquarium at Jennifer's face.
Jennifer remembers a part of her promise by the chapter's end: "I am yours, even in death."
September 1930 - The Goat Sisters
This chapter begins with Jennifer awakening in a room with Meg, who appears to be missing something. Meg then leaves Jennifer alone, pondering to herself.
Jennifer meets with Diana and Eleanor. From their conversation, Jennifer realizes that Meg is missing a love letter that she wrote to Diana. Diana, however, explains that she already received the letter and ripped it in half because she was sick of Meg following her all of the time. They then face Jennifer and ask her to find the other missing half of Meg's love letter.
The scent of the letter leads Jennifer to the Aristocrat Luggage room; inside, she fights the Goat Sisters, which are two goat Imps wielding scissors and a pitchfork. After defeating the Goat Sisters, Jennifer examines a grandfather clock in the room and discovers a goat's corpse and the other piece of the Meg's love letter in its stomach. Diana and Eleanor enter the room, with Meg behind them. Meg accuses Jennifer of tearing apart her love letter to Diana, and cries in Diana's arms.
Disgusted, Meg orders the Aristocrats to put Jennifer into the Onion Bag while the other children place various insects inside of it. Horrified and trapped, Jennifer faints inside of the Onion Bag. Jennifer comes to back in the same room in which the chapter started.
Jennifer remembers a part of her promise by the chapter's end: "even true love is quickly shredded by conflict."
June 1930 - The Gingerbread House
After the Bird of Happiness, Mermaid Princess and Goat Sisters chapters, Jennifer awakens in the Aristocrat's club room. This time, however, the mysterious boy is gone. As Jennifer leaves the room, a pair of sinister looking hands grab hold of her and pull her to the other side.
Jennifer then awakens in a beautiful rose garden at night with Gregory M. Wilson standing over her. He departs, mumbling something about his son, Joshua. Jennifer follows a path leading to Gregory's house. Inside the house, Jennifer remembers various memories with Gregory. In one memory, Jennifer remembers Gregory pointing a pistol to the side of his head, contemplating suicide.
In the house's basement, Jennifer finds Gregory who then locks her inside a decrepit room which she realizes was once Joshua's room. Wendy, seeing Jennifer in Joshua's room, sneaks into the house and unlocks the door. Jennifer meets with Wendy, and just before they make their escape, Wendy swipes Gregory's pistol.
In the rose garden, Jennifer exchanges a stuffed bear she found inside Gregory's house with Wendy's rose brooch. Wendy then names the bear Joshua.
October 1930 - Rag Princess Sews
After the ordeal in the Gingerbread House, Jennifer is back in front of the Aristocrat Club's door. The poster in front of the door now states that Joshua the bear is missing, and that the Aristocracy is searching for it. It also states that the reward for finding the stuffed bear is a red crayon.
Jennifer sees Gregory leaving a storybook outside of Amanda's room. Inside Amanda's room, Amanda is startled when Jennifer attempts to talk to her. Amanda asks Jennifer if she suspects her of stealing Joshua, and accuses Wendy of it. In Wendy's room, Jennifer finds her lying on the floor, out of bed. Helping her back into bed, Wendy reveals that the Aristocrats came and accused her of stealing Joshua the bear.
Searching for Amanda, Jennifer sees Amanda dragging what appears to be a corpse of her own body. Amanda escapes to the top of the airship via elevator, however, the power goes out before Jennifer has a chance to follow. Diana orders Jennifer to restore the power and upon doing so, Jennifer discovers that Xavier has stolen one of the power generator's levers. After finding the missing lever and restoring the power, Jennifer uses the elevator and on the top of the airship, she sees Amanda beating something with a stick. Amanda returns Joshua to Jennifer, and after realizing that Amanda is beating a handmade doll of her, Jennifer faints.
Waking up, Jennifer realizes that the mysterious boy has stolen Joshua from her. After a long chase through the airship, Jennifer is led to the door of the Aristocrat's club room, where she finds Joshua. Jennifer puts Joshua into the monthly gift box and the Aristocrats give Jennifer her own red crayon as promised. The Aristocrats suddenly disappear and hoards of Imps show up from nowhere; they tie Jennifer's body with rope and she faints.
November 1930 - The Funeral
Jennifer awakens in the Rose Garden Orphanage, tied up to a pole with rope. Her dress bears red crayons markings and she spits red crayons from out of her mouth. The sun is setting, and Hoffman tells the children via the intercom system that it is cleaning time. Jennifer calls Brown who is also in the same room and he frees Jennifer's ropes. In the orphanage's lobby, Hoffman accuses Jennifer of playing hooky again and orders her to help the other children with their cleaning.
Jennifer attempts to talk to the other children but all of them ignore her. Throughout the orphanage, crumpled pieces of paper are thrown at her with insulting messages such as "LIAR!" and "FILTHY!". One note tells Jennifer to go to the main hallway and when she does, the day turns into night and Hoffman wishes the children good night. Jennifer unfolds a crumpled paper and realizes in horror that she is now the monthly gift.
In the orphanage's courtyard, Jennifer sees Wendy through a window. The door to the courtyard is shut and after defeating various types of Imps scattered through the orphanage, the door becomes unlocked. In the courtyard, Wendy tells Jennifer that an important Aristocrat Club meeting is about to take place. Jennifer reads the storybook entitled "The Funeral", and when she is finished, she realizes that Brown and Wendy have disappeared.
In the club room, Jennifer has a hallucination of Brown's corpse. The Aristocrats appear, and Wendy reveals to Jennifer that she is the Princess of the Red Rose. Amanda whispers into Jennifer's ear that Brown is dead and points towards a bloodied sack with a large lump inside. Jennifer, fueled with rage, slaps Wendy several times, calling her a liar and vows to never forgive her. Jennifer then stands up to the Aristocrats, calling them monsters for siding with Wendy, and throws her rose brooch towards them. Wendy, humiliated and heartbroken, runs out the room sobbing.
December 1930 - Stray Dog and the Lying Princess
It's a rainy night as Jennifer awakens in her room in the orphanage. She hears laughter from Amanda and Susan, who beckon her to follow them. Amanda then shoves Jennifer into a room where the Red Crayon Aristocrat Club ask her to be the new "Princess of the Rose". Jennifer accepts, and Susan sees Wendy outside the orphanage. The girls, prepared to go outside and ridicule Wendy, head outside the orphanage. Jennifer, however, decides to stay inside.
Jennifer hears screaming outside and silently stands in fear of what to do. Suddenly, the front door to the orphanage opens and Jennifer sees the bodies of the other children. Joshua and Gregory are there, and Gregory is now "Stray Dog". Joshua sets him to attack Jennifer and after a battle, Brown (symbolically making her stronger) aids Jennifer. After defeating Gregory, Jennifer proceeds outside to find Joshua. Joshua reveals to Jennifer that he is actually Wendy, and she tells Jennifer that she brought Stray Dog for her own selfish reasons. Wendy apologizes and gives Jennifer Gregory's gun. Gregory, still alive, kills Wendy and faces Jennifer once more.
In this ending, Jennifer is unable to come to terms with her past. It is obtained by killing Gregory in combat. The screen slowly fades to black and a message on the screen states that Jennifer has wound up all alone again, unable to keep her promise or save anyone. Wendy's voice is heard, laughing maniacally as the game ends in "What a pitiful, unlucky girl."
This ending is obtained by giving the gun to Gregory. He suicides with it, and Jennifer runs into a bright light which escorts her away to come to terms with her past in the "Once Upon a Time" chapter.
January 1930 - Once Upon a Time
The player is now Jennifer as a little girl in the Rose Garden Orphanage as she reflects on her memories. As Jennifer exits the orphanage, she notices Wendy drawing in the dirt. Jennifer and Wendy greet each other with curtsies and kiss each other on the forehead. Jennifer travels through the front gate as it shuts on Wendy, who lowers her head in sorrow.
Jennifer reaches the shed and she gives Brown the collar she made for him. She remembers her promise that she once made to Wendy, and makes the same promise to Brown: "Everlasting. True love. I am yours." Jennifer then locks Brown in the shed, promising to protect his memory forever until her death.