What Are Good Third Date Questions?

The best questions on a third date are about what she wants, what she has loved, and what the two of you are like together. Ask one, say your own answer, and let the talk wander. Skip the biography questions you covered on the first date. She will not mind going deeper by now. She will mind being interviewed.

On the first date you traded facts: where you grew up, what you do, how many siblings. By the third, she knows those. A question like "so what do you do again?" tells her you were not listening.

The talk can now move from facts to feelings, and My sorting of topics shows why this matters. He sorts every topic into one of three groups. Third party topics are about neither of you. Some topics are about one of you alone. Others are about the two of you together. Facts and lists are mostly third party. They build friendship. The topics that build attraction sit closer to you and her.

coach lists dreams and aspirations among the best topics. They show who a person is becoming, and she has to picture a future while she answers. Try these:

• "What would you do with a year off and no money worries?"
• "What is something you want to be doing in five years that you are not doing now?"
• "What was the best stretch of your life so far, and what made it good?"

Then answer the same question yourself. A man who asks and never offers his own answer sounds like an interview. A man who trades answers sounds like a date.

These are the ones that make a third date feel different. They are light, a little flirtatious, and they put you in the same scene:

• "What did you think of me when we first met? Be honest."
• "Which part of the last two dates would you do again?"
• "If I planned the next one without telling you, what should I avoid?"

The first one is risky and it works, because it is playful. If she says "I thought you were a bit nervous," laugh and agree. Her honesty is worth more than a polished answer.

My example is travel. Listing the countries you have been to goes nowhere. Telling the story of the bus that broke down, and how you felt, goes somewhere. The same holds for her answers, so ask for the story.

• "What is the best trip you have ever taken, and what went wrong on it?"
• "What is a small thing you did that turned out to matter a lot?"
• "Who is the funniest person you know, and what is their best story?"

Funny stories about her friends and family tell you who she is. coach says personal anecdotes are among the strongest topics, because she is having a conversation with you that she could not have with anyone else.

The quickest fix for a stale question is to answer it before she does. My version: instead of "where are you from?", say "you seem like you grew up in a small town." You give her something to push against, and you show you have been paying attention.

On a third date, try: "You strike me as someone who keeps a plan and then throws it away for something better. Am I right?" She will correct you, and the correction is the conversation.

• Her past relationships. coach calls this a minefield: it can go well and it can sour the night, and if she raises it herself, keep it light.
• Where this is going, in the middle of dinner. If you want to know, say it lightly later and let her answer in her own time.
• Heavy political or religious debates, which coach tells men to keep off dates.
• Anything about how many people she has seen. It is none of your business yet, and it makes her feel judged.

My warning about questions is that three boring ones in a row usually end the conversation. So do not walk in with a list. Carry three good questions, ask the one that fits, and spend the rest of the evening reacting to what she says. If the evening is going well, you may not need any of them.