When someone is telling a story or about to tell a story, what part makes you think it's going to be interesting or boring?
Whenever someone has to highlight the fact that when they're telling a story from 30 years ago or longer, that they 'didn't have smartphones'. Like yeah, I don't expect someone from 1995 to have such a device and the closest things you've got were PDAs.
I just know it's going to be some old boomer like story that'll bore me.
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.
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.
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.
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.
That's because it's almost always a poor retelling.
When someone talks about their dreams, they're biased; to them, it's already profound. But to you, it sounds like a disconnected infodump because, well, it usually is.
I was in an apocalypse, then met Stu, he's 6 foot 4 and had 730 quadrillion molecules in his body, then Gandhi sold me to Justin Trudeau. Woke up in a cold sweat. (add 200 words of filler)
Is this a testament to the importance of writing skill, or insurmountable bias? I suppose a hobbyist writer would have a better chance at keeping one compelled.
Here's my favorite example of better dream storytelling: tumblr