Do you ever use them cross-generationally? I had a friend a dozen years my junior stop talking to me because I used a winking face when I wanted to make it clear I was kidding and he thought I was flirting with him. Never mind that we'd been friends for years and there had never, ever been a hint of interest between us. He insisted I should have known that's what it "always" means, never mind that I was using emoticons in AIM when he was in diapers.
This doesn't feel much different than words. There was a whole ordeal at Microsoft when an intern said an event was going to be "lit" and a bunch of older generation folk assumed that meant drugs.
Language changes all the time, emoji are just part of that.
This wasn't cheeky so much as self-deprecating enough that it was important to clarify I didn't actually mean it seriously. It would've sounded pretty dark otherwise.
