While Richie's parents may falter on occasion, it is never nearly as severe as the other parents of Derry, who demonstrate great neglect and abuse toward their children (i.e. She goes so far as to wish Richie had been born a girl so he would be able to better understand some of the things he does, demonstrating her desire to be a good mother to him. Richie's mother, Maggie, was kind and attempted to understand her son, but experienced some difficulty due to Richie's gender. While Richie's father did regard his son as a little silly, it's made clear that he cares about him and loves him dearly. Richie knew how to read his parents like 'well-worn and well-loved' books. Richie's father, Wentworth, was an intelligent man with a career in dentistry who would happily indulge Richie's interest in 'voices', going so far as to use some of his son's phrases himself. Richie is shown to have had a positive upbringing. Richie is known for his hobby of doing Voices and impersonations, although when he is younger most of them were awful and sounded the same. At some point in the book, Richie accidentally insults Henry Bowers and his gang out loud, resulting in him getting chased and almost beaten. Although Richie misbehaved a lot in school, he received good grades besides the grades in behavior. The other Losers often used the phrase 'Beep-beep' whenever they needed to silence him. He hated wearing the glasses, but found comfort in that one of his idols, Buddy Holly, was famous and also wore thick glasses. He wore thick black glasses and had huge front buck teeth which earned him the name 'Bucky Beaver' by others in his school, though he was later dubbed 'Trashmouth' by the Losers due to his foul language and loud mouth that often got him into trouble.

In the 2017/2019 adaptation, Richie is shown as the only one attending Stan’s bar mitzvah. He often teases the other Losers, especially Eddie and Bill, though it's generally mutual banter with Bill while he pokes fun at Eddie by referring to him as 'Eds', 'Eddie Spaghetti' and 'cute'.

He also thought Beverly was pretty, but perceived her as if she was the same as any other friend and even thought of her as “one of the boys”.

Like the others in the Losers' Club, he looked up to Bill and was cited as the one who 'understood Bill better than anyone'. As a child, his closest friends were Bill Denbrough, Eddie Kaspbrak, Beverly Marsh, Stan Uris, Mike Hanlon, and Ben Hanscom.

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