I suspect we're not taking about actual storytelling here as much as anecdotes that signal whether you will or will not agree with the rest of what's about to be said, but to answer the question as asked, imho good storytelling depends as much on the listener as the teller.

Some find joy to be infectious, they'll enjoy a story because the teller's eyes light up, and watching someone loving the shit out of something is itself a joyful experience.

Some will only enjoy a story if it's of direct positive relevance to them, regardless of who's telling it.

as a milennial who was very much alive and in school in 1995 (~5th grade for me), you may need to reimagine what a boomer is. my parents are boomers, lol.

Storytelling is about anticipation. Setting up the environment in which the narrative can unexpectedly take you somewhere.

When you next read anything, look at the mechanics of the process, what is revealed, when, how and why.

A lot of the time it comes down to how engaging the teller of the story is.

The same story could be told by two different people. One who's animated, emotionally engaged and who appears them self to be very interested, the other, who is the complete opposite of those things.

There are stories that I've found hilarious and/or engaging that upon reflection that were really just a load of pointless nonsense and vice versa stories that feel like they're boring and worthless at the time, but that upon reflection had real gold nuggets of information or wisdom.

This is why I'll always listen to others, I may end up no richer, but there's a chance that I will.

Bro you're off by like two generations haha. I'm I millennial and didn't have a cell phone till I was 17 or a smartphone till I was like 24.

But yeah sometimes I'll add that cause it's such an alien concept to kids. Like the story just doesn't make sense in modern context.

If someone starts the story by saying "I had a dream last night", I know it's going to be a long account of something totally nonsensical that I will be utterly uninterested in, that will not teach me anything of value, amaze me or amuse be in any way.

Depending on how much I care about not antagonizing that person, I might walk away without saying a word, lash out at them to shut them the hell up immediately, or politely listen while quietly escaping to my happy place in my mind while the torture lasts.

There are few things I hate more than people wasting my time telling me their dreams.