it has been SOOOO long since i did one of these but i felt like wasting my time today and kinda wanted to put the :B to rest (unlikely) so here is every emoticon john(/june) has used in canon homestuck (not including epilogues)
general takeaways are: there is legitimately no canon instance where they have used :B as an emoticon, people dont use emoticons enough in general when writing them, and omg this kid uses so many frowns ):