Maybe a good way to chat up girls is to imagine one of her future kids is present. Because if you actually do get the girl, you'll wind up entertaining her and her kid together a lot anyway. Obviously the optimal age-level of the imaginary lad or lass will vary, because girls are basically bifunctional playground equipment for men and children. Traits you neg her for now, you'll be negging her kids plenty for later. May as well start, to prove the rugrats won't roll you.
In other words, every guy needs to be funny. It's a basic part of having a family and kids.
I suspect that unfunniness and pompous writing are rooted in the same personality flaw.
I guess the people who know best how to fix unfunniness are standup comedians and PUAs, because both are exposed to ruthless immediate negative feedback.
That's treating a symptom. Maybe faking it till you make it works for some. But I doubt unfunniness is a symptom that should be treated directly, because that ruins its potential as a metric for deeper personality change. Funniness is correlated with dominance. Laughter is a pretty honest, objective signal about your own status. It's hard to lie to yourself about whether someone's laughing at you or with you.
Flawed animal charisma impedes one's popularity and political capital, regardless of substantive contributions. Atomized upbringing engenders personality flaws in animals, including humans.
The first step is realizing there is a problem. Self-awareness is integral to humor and humility.
The second step is not obsessing about short-term immutable flaws. This is pre-verbal ape stuff. Using linguistic thoughts to directly fix it is a category error.
Linguistic thoughts can hobble an ape-mind that's perfectly competent when the linguistic mind is suppressed by e.g. alcohol. I go to great lengths to suppress mine. Cyborganize drains my thoughts, koans discipline them, and ABCS grounds them.
It was easy for me to tell there was nothing wrong with my ape-brain, because my problems started abruptly at puberty. I went from bookish-but-fun to Spockish focus. The testosterone rush dramatically boosted my deepsocket orbitofrontal-cortex's performance, and I couldn't psychically compensate back to the American neurotypical baseline that prevailed outside my nuclear family.
It was like suddenly going from strong legs and normal upper body, to huge upper body. I lost the coordination necessary for basic social interaction. I abruptly had the turbo-focus to start questioning everything I'd received, whenever a discrepancy arose. Skepticism was the correct reaction to my cuckservative churchian upbringing, but the busy signal was disastrous for my social performance.
Considering my words more carefully compounded the communication barrier created by my high IQ by increasing the reading level of my speech. (See what I mean?) Then I took my blue pill anti-Game and strode forth boldly to woo those luscious feral teenage coeds.
So I had issues to work through, but a stable childhood goes a long way. Presumably I know nothing about fixing issues outside my experience.