Olivia's parents are divorced, with her mother living in Scarsdale.
Olivia is shown to be a typical teenage girl, though is referenced to have had a rebellious childhood. She reminisces with Karen about "glueing cookies to the floor and watching Mason get splinters trying to pick them up", and later joins Karen is throwing chestnuts at Rosario. 
She had a history of berating Jack, making fun of him for wearing Uggs and leaving him crying in the "fecal" position. However, she later becomes friends with him.
Olivia is shown to have a complicated relationship with Karen, at first being embarrassed of her when she attempts to hang out with her and her friends. However, they bond over their shared hobby of being cruel to the mansion's employees.
After Karen's divorce in season 10, Karen and Olivia go head to head in a mock trial in Will's class at Columbia Law School over a heart-shaped necklace that Karen lent Olivia and never got back. It is revealed that the necklace had been past down from mother to daughter and that Olivia had kept the necklace because she thought Karen had gifted her the necklace as a mother. Olivia reveals she had been hurt when Karen divorced Stanley without keeping in touch with her former stepdaughter. Karen reveals she also missed Olivia and the two make amends.
- As a child, her favorite show was Step by Step. Apparently, Karen paid for the show's production to last two extra seasons just so Olivia could watch it.
- She has Stanley's eyes, although, unlike his, they're "not on the sides of [her] head".