First date questions.

Light

• What does a really good Saturday look like for you? What would you add if money weren't a thing?
• Are you a morning person, a night person, or neither? What's the best hour of your day?
• What did you do last weekend? Was that a typical weekend or a good one?
• What's one small thing that always makes your day better?
• What's your go-to order at a coffee shop? Has it ever changed?

Curious

• What does a normal weekday look like for you, start to finish? Which part would you change if you could?
• What makes a day a good day for you? When did you last have one?
• Do you have any small rituals you keep, like a Sunday routine or a morning walk? How did that start?
• How do you usually wind down after a long week?
• What do you do when you have a free afternoon and no plans?

Deeper

• When you're stressed, what actually helps? And what do people do that doesn't help?
• What does taking care of yourself look like for you these days?

Light

• What's the best thing you've eaten this month? Where was it?
• What's a food you loved as a kid and still secretly love?
• If you could only eat one cuisine for a year, what would you pick?
• Are you a cook, a microwaver, or a takeout expert? What's your best dish?
• What's the most underrated restaurant around here?

Curious

• What's a meal you still remember years later? What made it so good: the food or the company?
• Is there a dish from your family that you'd want to learn to make?
• What's a food you hated and then changed your mind about?
• What would your perfect dinner party look like? Who'd be there?

Deeper

• Is there a food that tastes like home to you? What does home mean to you, then?

Light

• What's the best trip you've ever taken? What made it the best?
• Window or aisle? Do you sleep on planes?
• Where's somewhere you'd go back to tomorrow?
• Are you a beach holiday person or a city trip person?

Curious

• Where's the next place you really want to go? What's stopping you?
• Do you like a planned trip or figuring it out when you get there?
• What's a travel story that still makes you laugh?
• What's the most beautiful place you've seen in person?

Deeper

• Has a trip ever changed how you saw something?
• Is there somewhere you'd like to live for a year, just to see?

Light

• What do you do, and what do you actually do all day?
• What's the best part of your job? And the part you'd hand to someone else?
• What did you want to be when you were a kid? Any of that still there?

Curious

• How did you end up doing what you do?
• What are you working toward right now, at work or outside it?
• What's something you're learning at the moment? Why that?
• How do you keep work from taking over the rest of your life? Is that easy for you?
• If you could switch careers for one year, with no risk, what would you try?

Deeper

• What's something you're quietly proud of that most people don't know about?
• What would you do if you knew it would work out?
• What does success look like for you in five years, not just at work?

Light

• Where did you grow up? What was it like as a kid?
• Do you have siblings? Where are you in the lineup, and does it show?
• What were you like as a teenager?

Curious

• What's a favorite memory from when you were little?
• Who are you closest to in your family? What makes that relationship work?
• What's something your family always did that you thought everyone did?
• Which of your parents (or the people who raised you) are you more like?

Deeper

• What's something you learned growing up that you've kept? And something you've let go of?
• Is there a family tradition you'd like to carry on one day?

Light

• How did you meet your best friend?
• What would your friends say you're the one who always does?
• Are you more of a big group person or a one-on-one person? How do you recharge after a busy week?

Curious

• What do you value most in a friend?
• Who's someone who changed your life for the better?
• What's the best thing a friend has done for you?
• How do your friends know you're having a bad week?

Deeper

• What makes you feel appreciated? Is it words, time, little things, help?
• Have you ever had a friendship end? What did it teach you?

Light

• What do you do for fun when nobody's asking anything of you?
• What's a hobby you picked up and dropped? What made you stop?
• Do you have a guilty-pleasure hobby?

Curious

• What are you into right now that you could talk about for an hour? Go on, give me five minutes of it.
• Are you making anything at the moment: music, art, a garden, anything?
• What's a skill you'd love to learn this year?
• What's something you're surprisingly good at?
• Is there a hobby you'd like to try but haven't had the nerve?

Deeper

• When do you lose track of time?
• Do you give any of your time to a cause or community? How did you get involved?

Light

• What are you reading, watching or listening to right now?
• What's a song you'll never skip?
• What's a movie you can watch over and over?
• What was the first concert you ever went to?

Curious

• What's a book that stayed with you? Who would you give it to?
• Which song takes you straight back to a specific moment?
• What show or film do you recommend to everyone?
• Is there an artist or band you'd travel to see?

Deeper

• Has a book or film ever changed your mind about something?

Curious

• What's something you've changed your mind about in the last few years?
• What's the best advice you've ever been given? Did you take it?
• How do you make big decisions: list, gut, or ask everyone you know?
• What's a small habit that's made a big difference for you?
• What do you think you're good at that you used to be bad at?

Deeper

• What's a lesson you had to learn the hard way?
• What matters most to you right now?
• What's an experience that shaped who you are?
• What's something you're working on in yourself?
• What would the you of ten years ago be surprised about today?
• When do you feel most like yourself?

Light

• What's your favorite spot in this town? When do you usually go?
• City, suburbs, countryside: where do you feel best?
• What's the best thing about where you live right now?

Curious

• If you could live anywhere for a year, where would it be?
• What makes a place feel like home to you?
• Are you a pet person? Tell me about them, or the one you want.
• What's your ideal home look like: quiet, busy, full of plants, full of people?

Deeper

• Where do you see yourself settling, eventually, if you think about that?

Light

• What's your favorite holiday? What does it look like at your place?
• Big birthday or quiet birthday?
• What's the best party you've ever been to?

Curious

• What's a celebration you'll always remember?
• Are there traditions from your culture or family that you love? Which one would you want to share with someone?
• How do you like to celebrate when something good happens?

Deeper

• Is there a tradition you started yourself?

Light

• What's the most useless talent you have?
• What's a hill you'll die on that doesn't matter at all?
• If you had a free plane ticket for this weekend, where would you go?
• What's the last thing that made you laugh out loud?
• Would you rather have a personal chef or a personal driver?
• What's your karaoke song, even if you'd never sing it?
• Which fictional world would you most like to live in?
• What's the strangest job you've ever had?
• What's something everyone loves that you just don't get?
• What's your most controversial food opinion?

Curious

• If you could master one skill overnight, what would it be?
• What would your perfect day look like, start to finish, no limits?
• If you wrote a book, what would it be about?
• What's on your bucket list that would surprise people?
• If you won a small lottery, what's the first thing you'd do?

Light

• What's the best date you've ever been on (not counting this one)?
• What made you swipe right, or say yes to this?

Curious

• What do you like doing on a second date?
• What's something you've learned about yourself from dating?
• Do you like to take things slowly or see where things go?

Deeper

• What does a good relationship look like to you?
• What are you hoping to find, if you don't mind me asking?
• What makes you feel comfortable around someone new?