|The Tearful Princess|
|Voice actor||Emma Tate|
|“|| You deserve to be gobbled up.
Olivia is the youngest resident of the Rose Garden Orphanage, known as the Tearful Princess.
Olivia's main objective seems to be to get 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. 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.
Olivia is perceived as quite odd and hard to understand. 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 running around and around the post. Reason for this is unknown, although it can be suspected that she is doing it simply for childish fun, or perhaps, attention, in the company of her seemingly closest friend, Susan. 
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 (this may be due to age similarities).
Olivia is seen crying in various places throughout the game. If Jennifer tries to comfort her, she simply cries harder. She can be heard crying for her "daddy" during gameplay, which suggests that she had a good relationship with him before he supposedly died. His death may have indeed been the event that lead her to the orphanage.
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. Getting the wrong answers may have even been Olivia's way of getting Mr. Hoffman's attention.
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 because of her possible father's death, and like the Olivia from Twelfth Night, she also refuses consolation.
The name Olivia was derived from the name, Oliver, referring to the olive tree: the symbol for peace, beauty, and dignity. The "beauty" meaning may refer to her physical looks, while the "peace" meaning may be ironic, as it clashes with her inability to attain peace of mind. The "dignity" meaning also clashes with how she often cries, as it is seen as ignominious.
- "You deserve to be gobbled up."
- "Aman-da! Aman-da!"
- "Mr. Hoffman is really scary when he's mad..."
- (Crying) "Oh, Daddy, Daddy... Dad..."
- "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 right after Olivia is first introduced in the second chapter. If close attention is payed, the Imp can be seen, hunched over and crying, looking very much like Olivia. This is possibly a 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.
- Olivia is one of the only three characters to have one of their parents mentioned in the game. This includes Jennifer, who remembers her parents dying in the airship crash, and Joshua Wilson, who has Gregory M. Wilson as a father.
- Olivia bears a slight resemblance to Yonah from the video game, Nier.