Oliver is a character who was introduced in Dork Diaries 6, Tales From a Not-So-Happy Heartbreaker. He first appears when Nikki and Brianna run into their neighbor, Mrs. Wallabanger, at the mall. Mrs. Wallabanger is happy to see them and introduces her grandson Oliver. She asks Nikki to watch him while she stops over at Radioshack. When Oliver meets Brianna, he talks to her through his sock puppet, Mr. Buttons. Brianna responds by talking through her hand puppet, Miss Penelope. Brianna and Oliver quickly befriend each other. When Mrs. Wallabanger returns, she asks Nikki if she'd occasionally babysit him. She accepts the offer and teases Brianna about having a crush on him. When Nikki babysits him, he loses Mr. Buttons and Nikki gives him a sock puppet named Maxine that she made out of an old sock. Brianna finds Mr. Buttons and Oliver stops crying.He has blonde hair and his eyes are similiar to Mrs Maxwell's his eyes are honey brown
- He is Mrs. Wallabanger's grandson.
- He carries around a sock puppet named Mr. Buttons.
- Brianna says that her hand puppet, Miss Penelope, has a small crush on his sock puppet Mr. Buttons.
- Nikki says that he reminds her of a younger Brandon.
- He says that Mr. Buttons is an astronaut, with real moon dust, that he shows to Brianna/miss Penelope.
- When Mr. Buttons goes missing, Brianna insists he has been kidnapped by the tooth fairy.
- It is possible that Brianna and Oliver have a crush on each other.