The best questions to ask on a second date go one step deeper than first-date small talk. Start by following up on something they told you last time, then mix fun questions with a few about values and future plans. Share your own answers too, so it feels like a conversation, not an interview.
Below are 40 questions in four groups, plus tips for following up. If you want lighter openers, our sister site has a list of first date conversation starters. This list picks up where that one leaves off.
On a first date you cover the basics: work, where you grew up, what you do for fun. On a second date you already have material to work with, and a little more trust. That makes it a good time to go a bit deeper, gradually.
Research supports going step by step. The "36 Questions for Increasing Closeness" come from a 1997 study by Arthur Aron and colleagues and are shared by the Greater Good Science Center at UC Berkeley. The questions are grouped into sets that get more personal as they go, with partners taking turns answering. Greater Good says strangers who did this felt closer than pairs who asked small-talk questions, and notes that both people should be comfortable sharing first. The Gottman Institute makes a similar point about its date questions: some are good to ask now, and some are better saved for further down the road.
Nothing shows you were listening like remembering something from last time. Fill in the blanks:
"Last time you mentioned ___. How did that turn out?"
"Did you ever finish ___?"
"You said you wanted to try ___. Have you been yet?"
"I've been thinking about what you said about ___. How did you get into that?"
"How was the rest of your week after we hung out?"
What's the best thing you've eaten this year?
What's a hobby you dropped that you'd love to pick back up?
What's your most controversial food opinion?
What's the best concert or live show you've ever been to?
What's the most "you" thing you own?
What's a small thing that always makes your day better?
What were you like in high school?
What's a movie or show you can quote from memory?
What's the best trip you've taken, and what made it great?
Are you a planner, or a "see where the day takes us" person?
Would you like to be famous? In what way?
What's something you're weirdly good at?
Question 11 is one of the 36 Questions, from the first and lightest set.
These help you learn what matters to someone. Ask one or two, not all of them, and share your own answers. The first four come from the Gottman Institute's list of questions for dating partners, based on the book Eight Dates. The next three come from the 36 Questions (number 7 slightly adapted).
What does trust mean to you?
What does family mean to you?
How did you like to play as a child?
What's the most recent adventurous thing you did?
What do you value most in a friendship?
Is there something you've dreamed of doing for a long time? Why haven't you done it?
What's the greatest accomplishment of your life so far?
Who has had the biggest influence on who you are?
What's something you've changed your mind about in the last few years?
How do you recharge when life gets busy?
What's a cause or issue you care about?
What makes a place feel like home to you?
What's one goal you're working toward this year?
How do you feel about your work now, and how do you see it changing in the future?
Where do you want to travel in the next few years?
Is there a city you could see yourself living in someday?
What does a really good year look like for you?
What's on your bucket list that might surprise people?
Do you see yourself staying in this area long term?
What's a tradition you want to keep, or start?
What are you hoping to find in dating right now?
What would you do with a whole month off?
What's something you'd like to try on a future date?
Question 2 is also from the Gottman Institute's list. Question 11 doubles as a gentle way to plan date three.
Follow up more than you switch topics. Harvard Business School researchers found that people who asked more questions, especially follow-ups, were better liked, and in their speed-dating data the top third of question-askers got the most second dates.
Don't fire off a list. The same researchers warn that a barrage of questions without sharing anything yourself can seem guarded or even invasive.
Take turns. The 36 Questions work by both people answering. Do the same: answer your own question after they do.
Match their depth. If they give a short answer to a values question, keep it light and come back to it another time.
Follow the energy. When a topic lights them up, stay there. That's worth more than getting through a list.
Remember for next time. Their answers are your best ideas for a third date.
Second dates are a good time to go deeper, not all the way. Hold off on:
Detailed questions about past relationships
Exact income, debt or savings
Painful family history, unless they bring it up
"Where is this going?" pressure
It's fine to say what you're generally looking for, like something serious or something casual, if that matters to you. Being clear early is kind.
Follow up on what you learned last time, then mix fun topics with a few about values and plans.
Pick an activity that gives you something to talk about, open with a callback question, and share your own stories too.
Keep it light if it comes up. Detailed relationship history can wait until you know each other better.
There's no set number. Aim for a back-and-forth where you ask, listen, follow up and share in turn.
SecondYes: Second Date Planner helps with the plan around the conversation. For adults who have already met, it builds three date plans from your mood, budget, area and availability, and puts up to three options in one private link that the other person opens in a web browser. It needs no account, and your plans and history stay on your device.
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36 Questions for Increasing Closeness (Greater Good in Action, UC Berkeley)
Getting to Know You: Questions to Ask Your Dating Partner (The Gottman Institute)