It's a delicate balance between being polite (toeing your partner's comfort zone), provocative (so they actually have to think about the answer), and funny or i

It's a delicate balance between being polite (toeing your partner's comfort zone), provocative (so they actually have to think about the answer), and funny or interesting (catch them off guard, be entertained). When you're starting out you'll accidentally dip too far off either of these scales, but you can just apologise and calmly change tactic. Eventually you'll intuitively "feel" the conversation. And remember, some people are just too prudish, boring, or disinterested to be good conversationalists — feel free to politely "thank you" out of a conversation.