In It Chapter Two, when Richie is going through the Derry alone, he visits the old arcade and the park with the Paul Bunyan statue.
When Pennywise appears, he starts teasing Richie saying that
I know your secret, your dirty, little secret!
What was this secret?
The scene in the arcade might suggest that
Richie is gay
but I find it a bit hard to believe since there was no other indication for that, other than willing to share a token to play StreetFighter with another boy (who accused him rather to show-up in front of his cousin). Also in the book, Richie was divorced and was living a life of a celebrity, full of drugs and groupies.