Anyone who uses cocky funny through an entire interaction: every sentence out of their mouths being cocky funny lines is a fool.
David D even says don't use it like that, calling it a spice to the conversation. There are moments when it's appropriate to throw out a sarcastic remark that's lined with humor.
When I first got into the game like many guys the first book I read was double your dating. I went out doing it and offending people at first until I learned how to properly calibrate the technique and where it's best implemented.
I also had some natural charisma since I was a really random dude back then so it fit in well with my personality. I was just in the wuss area in terms of women and dating, and getting that monkey off my shoulder was one of the best things that happened to me in my life. Even though I offended a few people learning how to properly utilize the skill.
"If you want to make an omelet you have to break a few eggs."
For me it's all in the delivery. I'll often pause for a few moments right before the cocky "I can't believe you just said that" part. Often to the lead up I'll be talking about stuff that leads them to think I will say something different so the cocky part has surprise shock value. Anyone familiar with comedic formula knows what I'm talking about.
Anyone on here who says that "this won't work for you because you're not naturally funny" is spitting bullshit. Most people laugh at shit that isn't of the funny variety. It's more surprise, awkwardness, anger etc. Just get a book about comedy and read through it and you will be able to use this technique.
A few places I whip out Cocky-Funny-No-Jutsu
She makes a sarcastic remark towards me, or says something really stupid.
She asks me a silly question. I'll answer it with a cocky funny line. If she presses after the bs response I gave her, then I will answer her honestly.
If she asks me a normal question. I sporadically alternate cocky funny responses vs honest ones.
I see something that I don't like about her reality. I point it out in a cocky funny way.
I don't talk about permanent insecurities, but with humor you honestly can talk about anything. You have comedians talking about racist shit all of the time, masking it with humor. They talk about presidents, diseases,beating kids, choking and raping women, wars, death, anything! Some comedians piss me off. That's what they aim for a ton of the time.
You just tailor the shit to the audience. If you understand the woman who you are dealing with then the use of cocky-funny is limitless.