Jessica Douglas, Mrs. Douglas, or Cupcake, is an ordinary middle-aged Mother. Jessica is a business woman living in a two storey Cape Cod. Along with Pumpkin's father Charles, she is often away from home. This leaves Pumpkin home alone most of the time and is a contributor to Pumpkin's depression. She is most notably seen arguing with Charles in Pumpkin's flashback. Pumpkin believes that Charles and Jessica tried to poison him with arsenic when he was just three years old ultimately resulting in Pumpkin's hospitalization.
- Jessica is a middle-aged mother with a jet black curly 80's style perm and triangular earrings. She is usually seen in a long green pencil skirt and a white button-up business shirt or blouse and white kitten heels. Her eyes are the same lilac-silver colouration as her son's.
- She's an overly bubbly cooking enthusiast who speaks with a noxious and high voice likened to that of a chipmunk. Her incredibly thick accent is responsible for nurturing Pumpkin’s accent.
- She has a food related nickname though her husband does not appear to have any nickname at all.