I'm looking at this and this for basic text emoticons, and some of the standard graphical ones we use today aren't really easily done in text, and don't seem easy to do in monochrome without the use of gradients.
I'm wondering if one could offer some suggestions how to potentially convert the following standard emojis to something monochrome (and gradientless, i.e. basic vector).
You'll notice on the Wiki link that many of these have close variants that are doable in plain ascii, but I selected the ones that I thought would be harder. Specifically, the long tears, the hearts, the blushing, the subtle happy eyes. I am in particular wondering about for small resolution, like what you see when you paste an emoji here for example: ☺️. Maybe a little bit larger, that's pretty small. It's the gradients mostly that make it seem difficult, as well as the intricate detail in some of them.
If I try to draw the first one in monochrome it looks like a clown :'(