Cocky/Funny help

I feel that the person I am (Black, masculine, BLACK ) makes it good for me to use the cocky/funny technique. But I haven't quite got it down yet, its my 3rd day on the forum and I'm trying to grasp all of this. Some questions i have about Cocky/Funny

1. Whats the difference between cocky/funny and arrogant/annoying? And is there a fine like between cocky/funny and arrogant/annoying?

2. How often should i use cocky/funny? Everytime she sets herself up for it, or sparringly just when i need to spice things up?

3. How can i use cocky/funny effectively in a convo? I seem to always do it somehow like this (real txt convo):

Girl: Is it weird for you to text me and my sister at the same time?

Me: Mm honestly not really. Is it weird texting me knowing your sister is too? Cuz if theres competition i can always just stop texting one of you

Girl: Lol no I dont care. She wants me to stop texting you. She HATES that I talk to you.

Note: Girl is two years older than I am, girls sister is my age.

Did I get a good reply out of the girl? What should I of said? I feel like i know how to use it but not to the right effectiveness. I see people using it in a sexual way or in a way that builds rapport or in a way that makes the girl open up more and moves the "relationship status" further down the line. Thanks to whichever PUA replies to this

1. the difference is the reaction ,if the female laughs then your doing it right, but if she has that look of digust in her face, its time to ease on the cocky and funny a little bit , the line actually varies depending on the girl, some can take jokes others with low self esteem cant
2.be playful with it, cocky and funny is meant to spark attraction, but dont over do it cause that makes you look full of yourself and it makes you look like a clown
3.cocky and funny can be used any time but dont use it when the female is in an emotion state, thats when cocky and funny is a big no no, great text example, wouldnt change a thing it looks like the girl is falling back and giving her sister a chance

sexual cocky and funny is usually innuendo like "I need help when I pee, my doc said I shouldnt do any heavy lifting" its gets a laugh here and there but I wouldnt recommend it