I don't think it's a common expression. It seems quite specific. Most people who don't know about the Pennywise character from 'It' would be confused by this phrase. It's really something that would be used within the context of discussing that particular fictional character and its related stories.
You need to familiarize yourself with the rules and mechanics of the game. Start by reading the instructions carefully and maybe watch some tutorials online.
It could mean that Pennywise, perhaps referring to the character from 'It', has a repetitive or unchanging story. Maybe it implies that the actions, motives or the general narrative around Pennywise are always the same.
They can start by simply reading it. Look for fanfic platforms like Archive of Our Own or FanFiction.net. Once they find a new pennywise fanfic, they can leave comments to share their thoughts, especially if they are an old reader with a different perspective. They can also join fanfic - related forums or groups dedicated to Pennywise to discuss the new fanfics with other fans.
One idea could be a story where an old reader of Pennywise stories discovers a new fanfic that reimagines Pennywise in a modern, more complex way. For example, the new fanfic might explore Pennywise's origins in a different dimension or with a different set of motives. Another idea could be a crossover in the fanfic where the old Pennywise from the original stories meets the new interpretation, leading to a clash or an unexpected alliance.
This phrase implies monotony. Say there's a workplace where the boss always gives the same unachievable targets, and the employees always have the same struggle to meet them. It's a pattern that doesn't change, so we use'same old story' to describe this unchanging and often tiresome state of affairs.
Pennywise is a malevolent clown from the horror novel 'It' by Stephen King. It preys on children and resurfaces every 27 years to terrorize the town of Derry.
One way is to step out of your comfort zone. If it's a personal 'same old story' like always choosing the wrong type of friends, be brave and make new connections in different social circles.
Pennywise is purely fictional. It was made up by the author for the purpose of scaring and thrilling readers/viewers. There's no real-life basis for this character.