How to write a short story
Deep Dives
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O. Henry
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Assortative mating
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My opinion is that a short story should start right away with some kind of desire. Right away, from the very first line. There’s no need to be coy.
“Ellie wanted to marry a wealthy man.”
Then, as you’re writing the story, you think, What would be an extremely boring way to tell this story? And you don’t tell it the boring way. You subvert the boring-story expectation and do something different instead.
For instance, if Ellie was some upper-middle-class girl who’d gotten tired of the career treadmill and decided to go ‘trad’ then that would be extremely boring, so I won’t write it that way. Instead I’ll do something different:
Ellie wanted to marry a wealthy man, but she couldn’t find any. She lived in SF, and everyone here was supposedly so rich, but all the guys she matched with online were townies, like her, still lived with their parents, worked at Best Buy. What about these guys who drove Teslas? Or even just those expensive e-bikes—she’d looked up some of these bikes. They could cost $6,000. The guys on these e-bikes wouldn’t even look at her!
So now it’s a story about a lower-middle-class girl who’s trying to crack the code on these nerdy engineer types. Which seems pretty funny. Like, that’s a good story right there. At each stage, you just think, “What do readers expect?” And then you don’t do that thing.
Also, pretty early on, you should introduce some other characters and create a milieu.
Ellie was part of a Discord server where girls traded tips on how to catch classy guys. This forum had its own lingo. And in this Discord there was a lot of debate on who to go for. Some people said you needed to look for Safe Bets—guys who were in a business where someday they’d make a lot of money. Like someone who was in med school. Other people said no, you needed a Sure Thing. That was somebody who already had money.
The girls in this forum spent a lot of time psychoanalyzing these guys and figuring out what they wanted from a woman. They had developed this whole ideology that actually these high-earning guys were tired of these career women, who were ugly, sort of frigid, poorly-dressed. Really they were attracted to girls like Ellie: traditional, hot, feminine girls. But they felt punished by society
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