90 Questions to Ask on a First Date

First dates come with their own set of challenges, especially when it comes to conversation. You want to be engaging, ask the right questions, and, most importantly, enjoy yourself.

It’s about finding that sweet spot where the conversation just flows.

To make things easier, I’ll share some questions designed to spark genuine conversations, ensuring you both have a wonderful time getting to know each other. Ready to impress and have some fun? Let’s get started!

Getting to Know Each Other

1. What do you enjoy doing in your free time?
2. What’s your favorite book or movie?
3. How do you like to spend your weekends?
4. Do you prefer the city or the countryside?
5. What’s something interesting about your hometown?
6. What’s your favorite way to relax?
7. Do you have any pets?
8. What’s your favorite type of music?
9. Do you enjoy cooking?
10. What’s your favorite season of the year and why?

Shared Interests and Hobbies

1. What hobbies are you passionate about?
2. Do you enjoy any sports?
3. What kind of outdoor activities do you like?
4. Are you into any arts or crafts?
5. Have you picked up any new hobbies recently?
6. Do you play any musical instruments?
7. Are you a fan of any particular TV shows?
8. Do you like reading? If so, what are your favorite genres?
9. Do you enjoy gaming, and if so, what games do you play?
10. What’s your go-to activity for fun?

Family and Background

1. Do you have any siblings?
2. What was your favorite family tradition growing up?
3. Where did you grow up?
4. Do you come from a big or small family?
5. Are you close to your family?
6. What’s the best advice your parents gave you?
7. Do you have any family holiday traditions?
8. What language(s) does your family speak at home?
9. Do you have any fun family stories or memories?
10. Did you have any childhood pets?

Life Goals and Values

1. What are your top priorities in life?
2. Where do you see yourself in five years?
3. What does success mean to you?
4. Do you have any personal goals you’re working towards?
5. What motivates you each day?
6. How do you handle challenges or setbacks?
7. What’s a cause you feel passionate about?
8. Do you have any life philosophies you live by?
9. What kind of legacy do you want to leave?
10. How important is work-life balance to you?

Fun and Lighthearted Questions

1. What would you do if you won the lottery?
2. What’s the silliest thing you’ve ever done?
3. If you could have any superpower, what would it be?
4. What’s your favorite joke or funny story?
5. What’s the most adventurous thing you’ve ever done?
6. If you could travel anywhere, where would you go first?
7. Do you have any funny nicknames?
8. What’s your go-to karaoke song?
9. If you could meet any celebrity, who would it be?
10. What’s your favorite way to procrastinate?

Work and Career

1. What do you do for work?
2. How did you choose your career?
3. Do you enjoy what you do?
4. What’s the best part of your job?
5. What’s the most challenging part of your job?
6. Do you work with a close-knit team?
7. What’s a typical day at work like for you?
8. Are you working on any exciting projects at work?
9. What’s your dream job?
10. How do you balance work and personal life?

Travel and Experiences

1. What’s the best trip you’ve ever taken?
2. Do you prefer beach vacations or city adventures?
3. Have you ever traveled solo?
4. Where’s the next place on your travel bucket list?
5. What’s the most unique place you’ve visited?
6. Do you enjoy road trips?
7. Have you ever experienced culture shock?
8. What’s your favorite travel memory?
9. Do you like trying new foods when traveling?
10. What’s the longest flight you’ve ever taken?

Entertainment Choices

1. What’s your all-time favorite movie?
2. Do you have a favorite TV show you’re binge-watching?
3. What kind of music do you listen to?
4. Who’s your favorite band or artist?
5. Do you prefer watching movies at home or in a theater?
6. Have you been to any concerts recently?
7. Do you like going to live theater or musicals?
8. What genre of books do you enjoy?
9. Do you listen to podcasts? If so, which ones?
10. What’s the last book you read?

Food and Drink Preferences

1. What’s your favorite type of cuisine?
2. Do you like to cook or prefer dining out?
3. What’s your favorite restaurant?
4. Do you have a go-to comfort food?
5. Are you a coffee or tea person?
6. What’s your favorite dessert?
7. Do you enjoy trying new foods?
8. What’s your favorite drink, alcoholic or non-alcoholic?
9. Do you have any food allergies or dislikes?
10. Are you adventurous with food, or do you stick to what you know?