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.
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.
Well, there's a new type of coffee blend that combines Ethiopian beans with a rare Indonesian variety. It has a unique flavor profile that's both fruity and earthy at the same time. It's been making waves in the coffee connoisseur circles lately.
There's a new app that uses augmented reality to let you see how furniture would look in your home before you buy it. It's super handy and has made shopping for home decor a lot more fun and less of a gamble.
When we hear 'it's the same old story', it implies a sense of boredom or predictability. Say in a workplace, if the boss always gives the same unachievable deadlines and blames the employees in the same way, that's the same old story. It can be used to express exasperation about a situation that refuses to change and keeps repeating itself in an annoying fashion.
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.