Like Cornflakes said, it's very difficult to get your true intentions across over text. I prefer to keep texting and instant messaging to a minimum for this reason. These kid of interactions can very easily drop you into the friend zone.
You obviously need to portray confidence when talking, not just with women but with men as well. You can't be a stuttering pile of nerves! From my understanding, correct me if I'm wrong, the concept of cocky funny is to be able to portray that confidence but in a joking way. The joking style of the delivery stops you sounding arrogant. Let's be honest, who wants to be around somebody who is arrogant? Certainly not me. You need to remember that all though you're trying to be the centre of her attention, relationships are a two way thing. She needs to be able to get a word in a feel like she is part of it. After all, everyone's favourite subject, themselves.
Obviously, take my words with a pinch of salt as I am no expert. Hope the advice helps though.
I like your post and.. yea i really never text much anymore cause it does seem like you slip in the friend zone having often contact