How do you play the arranged marriage angle without it feeling flat?

New to this one. The setup is Kai inheriting everything on the condition of an anonymous arranged marriage his father set up, and the opening frames it as purely transactional, no names exchanged yet. I tried playing it cold and matching his 'nothing more than a transaction' framing but the conversation just stalled out fast. Is there a better way to open that actually gets some movement out of him, or does it stay businesslike for a while by design?