The list runs from easy openers through the first months of dating to living together and the future. If you’ve only been seeing him a few weeks, stay with the openers and the questions about his world. If you’ve been together for years, go to the groups further down. Either way, start with an ordinary part of his week, such as a meal, a friend or something he’s looking forward to. You can stay with the easy questions for a whole evening.
Follow the detail he offers
If he mentions a childhood place, ask what he did there and who was with him. Avoid using each answer to check how closely he matches an ideal partner. Share your answer too, without expecting the same amount of detail in return.
Ask about his people before you meet them
Questions about his friends and family are easy to answer and useful later. If you know who taught him to cook or which friend he calls after a bad day, you’ll have something real to talk about when you meet them. Let him decide how much to tell you about a difficult relative.
When you’ve been together a while
After a year or two, it’s easy to assume you know his answers. Ask about this week rather than his life in general, and ask for a story from before you met. If his answer differs from what you expected, ask when that changed.
Before you move in together
Take one practical area at a time: chores, rent and bills, guests, time alone. Say which parts you’d want settled before the move and which can wait. Write down what you agree so neither of you remembers it differently later.
When the future comes up
If he asks where you see this going and you don’t know yet, say so. Questions about moving, marriage or children are worth asking once the answer would change something you’re deciding. Until then, “what do you want next year to look like?” is enough.
When he doesn’t want to answer
Accept the pass and change the subject. You don’t need to persuade him to share something private. For more on a life you already share, try questions to ask your partner.