nathanael.ink

A: You know they say winky-faces in texting is the leading cause of male insecurity

B: Hahaha WHAAAT

If anything, I would assume the opposite to some degree. 

A: Haha 😉

a winky-face to me says: the context in which these words were said does not immediately reflect the way I meant them.

The ambiguity leaves the positive or negative element up to me. So it constantly conforms to my presupposed concept of myself, of how people “ought” to see me
Thusly its negative

B: Incorrect analysis, my friend. Winky faces are necessary to insinuate facetious jesting which could otherwise not be registered by the recipient.   

A: Exactly though. To be a facetious jest, it assumes it’s inappropriate. Thus not appropriate in the context it would otherwise be considered appropriate in. So I’m left wondering how to frame the jest, what to make of it. One could be meaning anything as subtle as slightly more light hearted then perhaps the words would be read OR as extreme as meaning the complete opposite of what was said. And there is no clarification of the winky-face. No rules for which it ought to be engaged it.
Know what I mean 😉

B: I think it is then up to the recipient to decipher, which I don’t think is as complicated or grueling as you seem to insinuate.  if I were to say “go jump of a cliff! 😉 ” I should certainly hope that you know I am in no way actually suggesting such a thing. If I say “it’s not too late! 😉 ” it is sincere, though playful.. Suggesting that you really could do such a thing, if you wanted.  Duh. 😉
Also, where do you come to the conclusion that jesting is inappropriate?! I don’t approve such nonsense.

A: fa·ce·tious /fəˈsēSHəs/

Adjective. Treating serious issues with deliberately inappropriate humor; flippant.

B: The Bible says “course” jesting, which then I would assume harsh/foul/inappropriate-ness.
NOT!! Where are you obtaining such ridiculousness ?
fa·ce·tious /fəˈsēSHəs/

Adjective. Amusing; humorous. Lacking serious intent.

Oh, the battle over words.

A: Hey giiirl. You said it. Not me.
Take it up with merrium webster

B: Merriam * 😛

A: Well played 😉