I come across as very arrogant often. I have problems finding difference between being arrogant and cocky/funny.
Here are two text examples with girls that I already had sex with:
1) Texting her next day after the evening of "watching game of thrones".
Me: Lets have sex only once per game of thrones episode..

I want to watch 3rd seasson some time.
Her: Haha, ok, "till the end" once. .. what about everything else??

// (we had sex with penetration once last night, but lots of oral)
Me: Haha, so you are saying it stays 5 min GoT, 2 hours of sex ratio?
Her: Something like that. Than we can restart episode and actually watch it

Me: That sound familiar..

Lets test our discipline. Next time we watch 10 mins, without sex!

Her: Put crocs on and there will be no problems

Me: I'm so good looking in crocs, that you wouldn't even press play ..
...
2)
Her: How's the studying going?
Me: Well, I'll probably pass.. Right now I'll make myself hot warm bath.

Are you partying?
Her: I really want to join you in bath!

No, I was shopping and I'm way too tired ..
Me: (sending top less photo with my 6-packs) Look what you are missing

Bought anything?
...
I would be very thankful if someone analysed these two conversations, backed with some theory and why does it work that way.
What kind of reply would you expect? (I can post how conversations continued.)
Thank you for reply!