lookism bros, give me your texting rizz tips

[Mr Looks]

do you ever just not know what to say though? and then you begin thinking about the right thing to say, but then you start overthinking and before you know it, you dont know what sounds natural or not anymore

There is no right and wrong, just say the first thing that comes to your mind. You are not shaekspeare; don't try to be literature mogger, words are just a tool to convey feelings.
Imho what you say doesn't matter in the slightest, it's all about being confidently playful and having fun
But be dignified and serious when it comes to things that hurt her