sure!

Talking about daily life works pretty well (general chit chat - asking people how they’re feeling, what they’ve been doing, assuming you know something about their lives already there won’t be many ambiguities). online, I often share pictures as I go (they give points of reference). So I can say “mi pali e pan suwi” (i made sweet bread) and show a picture of a cake; my friend could say “ni li pona ala pona?” (is it good or not?) and I could reply appropriately. I could say if I plan to make it again, maybe talk about the ingredient composition slightly.

Commonly also, sharing toki pona memes/making jokes, finding deliberately silly ways to refer to things. (A running game I have with a friend is referring to lots of places as “tomo awen” (waiting house). Hospital? “tomo awen”, because most of your time there is waiting. Waiting in line at a supermarket? “tomo awen”. And right now, our homes are also “tomo awen”, because we can’t go out...).

One thing I’m looking forward to doing when it gets warm/we’re not quarantined anymore, is going to the zoo, walking around, and deciding how to describe all the different animals “soweli pi lawa sewi” (animal with a high head) for giraffe for instance. Going to a gallery or the like would also probably work pretty well - you can point at things, talk about how you feel about them. (It would be more about immediate experience than prior knowledge I guess). Any activity/situation with a lot of ready-to-hand context is likely to work.

Doing activities where you have a fixed frame of reference a language with limited vocabulary can work quite well. I played 2-player local coop of Wilmot’s Warehouse ( https://www.youtube.com/watch?v=TAcyPIJYOx4 ), where the sould of the game is categorising packages with various random/abstract designs and deciding where to put them in a warehouse. That would probably be a good exercise for any language, but it worked in toki pona.

I met up with someone I didn’t otherwise know and we talked about our professions, where we grew up, etc. (One cheat is that in Toki Pona’s 120 word count, borrowed words aren’t included - but there are conventions for transliterating words from other languages if you want to talk about English (Inli) or America (Mewika)).

You can go shopping and cook with someone - trying to describe what ingredients you’re looking for is I guess a game, and once you have them at home you can probably issue instructions with enough accuracy using Toki Pona’s vocabulary.

What’s difficult to talk about? Time and scheduling, especially under time pressure. Trying to clear up a scheduling confusion via txt messages with a friend was absolutely zero fun, especially when misunderstandings start creeping in that can’t be quickly rectified. Scheduling discussions have been the ones where I’ve hated Toki Pona the most.

Talking about technical matters doesn’t work - I can’t talk meaningful about maths in toki pona beyond the absolute vaguest of euphemisms - and while people have tried to state theorems/etc., it basically doesn’t work in my experience.

Talking without a concrete frame of reference can be hard. If I can’t see you, can’t share pictures with you, can’t use emoji, etc., the range of what I can communicate is severely limited. I can say I worked, I can say I’m feeling good, I can say what country I live in. I can talk about eating flat round bread with red paste on top (pizza), and that my girldfriend didn’t like it or whatever...which is still manageable chitchit I guess, but much more limited. (There are toki pona songs that work well at this level of speech though - e.g. https://www.youtube.com/watch?v=Bjlwov4JiD0 ).