|The Tearful Princess|
|Voice actor||Emma Tate|
|“|| You deserve to be gobbled up.
Olivia's main objective seems to seek attention, which was most likely the thing she lost when she was sent to the orphanage. She also seems to be very impressionable. During the "Unlucky Clover Field" chapter of the game, she is first seen crying over a dead butterfly. When Jennifer bends down to pick it up, she shoves a fork into the ground, nearly stabbing her hand. She then leaves the room with the words: "You deserve to be gobbled up." With this incident, it could be deduced that she, like the rest of the orphans, also has a malevolent personality that she is developing from witnessing the other children's mischievous behavior.
In the "Goat Sisters" chapter, if Jennifer attempts to enter the filth room, Olivia and Susan will keep her out. If Jennifer goes into the next room and peeks through the crack in the wall, Olivia can be seen playfully running around and around the post.
Olivia is in the Bourgeoisie class of the Red Crayon Aristocrat Club. She can be seen as the "partner" of Susan, as they are usually seen together.
Olivia is seen crying in various places throughout the game. If Jennifer tries to comfort her, she simply cries harder.
Olivia is seen standing in front of a blackboard in the "Sir Peter" chapter of the game, on which are some simple mathematical equations. If Jennifer attempts to talk to her, she immediately hunches over and says, "Mr. Hoffman is really scary when he's mad..." after which, she begins to sob. This could possibly mean that Mr. Hoffman was trying to teach Olivia, and became frustrated due to her not understanding the material.
In "The Funeral" chapter of the game, Olivia can be seen in the kitchen, attempting to reach a pot, which is up on the counter. There seems to be no apparent reason for this, as there is nothing in the pot; thus it can be deemed as another one of Olivia's attempts to receive attention. It may also be noted that if she were to jump up, she would have indeed been able to reach it. As soon as Jennifer approaches her, Olivia hunches over and begins to sob once again. When Jennifer attempts to comfort her, Olivia simply cries harder - this could suggest a spiteful characteristic.
She and the other girls attempt to apologize to Jennifer by showing her great respect before her life is ended in the Rose Garden Orphanage massacre.
In the "Once Upon a Time" chapter, Jennifer states: "Olivia, the one who cried all the time, stopped crying completely when all the adults were gone. With no teacher to give her attention and no cleaning lady to scold her, there was no point in crying anymore... Poor Olivia."
Olivia's name was most likely derived from the character, Olivia, from William Shakespeare's play, Twelfth Night. Much like the Olivia from Rule of Rose, this Olivia is a very emotional character, who also allows her feelings to get the best of her. In the play, Olivia has lost her brother and remains grief-stricken, rejecting all visitors that come to console her, claiming that she will remain in mourning for the next seven years. In Rule of Rose, Olivia is often crying for various reasons, and like the Olivia from Twelfth Night, she also refuses consolation.
- "You deserve to be gobbled up."
- "Aman-da! Aman-da!"
- "Mr. Hoffman is really scary when he's mad..."
- "Jen-ni-fer! Jen-ni-fer!"
- (Crying) "No way! There's no such thing!"
- "Hats off to you! Hats off to you!"
- The first enemy of the game is seen after Olivia is introduced in the second chapter. The Imp is hunched over and crying, looking very much like Olivia. This is a possible reference to what Olivia says to Jennifer upon first seeing her, as Jennifer's fear of being "gobbled up" may have been channeled into the actions of the Imp.
- In the "Sir Peter" chapter, near the blackboard, Olivia can be heard crying. If one were to listen closely, they might hear her sobbing for her "daddy" but this is unknown.
- Olivia bears a slight resemblance to Yonah from the video game Nier.