Will it come off as manipulative to play a game of “How would you feel if I dated/slept with ____”? We’re getting started with poly again and he isn’t very good about communicating his needs, but I need to know his boundaries.

This one will be short and sweet:

1.) If you’re worried about whether something seems manipulative, it probably is. That kind of conversation isn’t necessarily manipulative (and should happen in any healthy poly relationship) - but if you’re doing it to trick, wheedle, coerce, etc. - then there’s a problem.

2.) If he’s not very good at communicating his needs, he’s not ready to be in a poly relationship. The onus is not on you to cajole him into communicating his needs and boundaries. If you’re this worried about how to have this basic conversation, the relationship is not ready to be opened up.

This issue here is not how to word specific questions - it’s the fact that you can’t have a clear, open, honest conversation about needs and boundaries. That needs to be solved, not patched over.