Oh man I knew someone would ask me this one. :X After thinking about it, this is what I came up with, lol. Craig seems like the type to me to not make a big deal out of it… like just dropping it over breakfast or something.
If it was the other way around, I think Tweek would know that Craig would get really angry/annoyed by a public proposal, so he’d want to do something more private while still trying to make it vaguely romantic, like trying to cook a nice dinner or something… but he picks dishes that are too ambitious and he flubs the meal… Craig eats it anyway because he’ll eat anything… and he has absolutely no idea what’s going on until Tweek pops the question. Then he promptly chokes.
I’m not sure how gay couples usually approach this, engagement rings aren’t typically a thing for guys… I don’t think Craig would bother getting jewelry if he proposed but Tweek might buy Craig a nice watch or something.