75 Creative First Date Questions to Ask Anyone

A couple asking each other dating questions while on a first date at a fair.

With every first date comes a flurry of excitement. Will you hit it off? Will sparks fly? What if he or she ends up being the one? But dates can also bring up nerves. What if you have no chemistry? What if there’s something in your teeth? What if you have nothing to say to each other? Fortunately, we can help with that last one using a few creative first date questions that will help you start a conversation with anyone.

Whether you met your date online, through friends, or out in the world, there are bound to be things you don’t know about him or her. So it’s important to ask some questions to get to know the person better. Even if you don’t turn out to be a perfect match, you can still enjoy the other person’s conversation and company.

So here they are—75 creative and thoughtful first date questions to keep in your back pocket:

Work
• Have you ever changed career paths?
• Do you have, or have you ever had, a mentor?
• How’d you get started in your career?
• Did you go to college? What was your major? Where did you go?
• If you could have any job aside from the one you have now, what would it be?
• Do you ever see yourself going back to school?
• Did you always want to do what you do now?
• What do you like about what you do?
• What’s your schedule usually like?
• Do you like your boss and coworkers?

Family
• Are you close to your family? Do they live nearby?
• Does your family have any special traditions?
• Do you have a big family?
• How did your parents meet?
• Where did your parents grow up?
• Where is your family from?
• What was the most memorable family trip you took as a kid?
• Is there anyone in your family you really look up to?
• What’s your favorite holiday tradition?
• Which family member are you most similar to?
• Which family member are you closest too?

Growing Up
• Where did you grow up?
• What were you like as a kid?
• Did you ever get in trouble in school? With your family?
• Where did you make your closest friends?
• What was your favorite age?
• What was your best year?
• Would you go back if you could?
• Did you play any sports as a kid?
• Did you play an instruments as a kid? 

Pop culture and entertainment
• What’s a book that you’d love to see be made into a movie?
• Do you listen to any podcasts?
• What actor would play you in the movie about your life?
• What TV show do you think was cancelled too early?
• What’s the last book your read?
• What’s the last show you got addicted to?
• What’s the last movie you saw?
• Any good movies you want to see that are out right now?
• What are you listening to right now?
• Who are your favorite artists or bands?

Hobbies
• What do you usually do on the weekends?
• What did you do last weekend?
• What’s the last trip you took?
• Do you have any trips planned?
• Whats your next adventure going to be?
• Have any special skills you could teach me or introduce me to?
• What’s something you’ve always wanted to try?
• What’s your hidden talent?

Dating 
• What made you ask me out/accept my invitation?
• How long have you been single?
• What was the longest relationship you ever had?
• Do you date a lot?
• Are you a dating pro or a novice?
• Do you have any dating horror stories?
• Have you ever tried online dating?
• Are most of your friends single, dating, or married?
• When was the last time you went on a date?

Grab bag
• What’s the last thing you Googled?
• What’s your spirit animal?
• What’s your perfect New Year’s Eve?
• What’s your favorite joke?
• What’s your guilty pleasure?
• What’s in your freezer right now?
• Ever get a tattoo?
• Do you cook a lot? Do you enjoy it?
• What are your favorite restaurants in the area?
• What’s your favorite drink? Are you a beer or wine person?
• Are you a coffee junkie?
• Are you a big social media person?

These first date questions are a great way to break the ice, settle into a date, or keep the conversation going when you feel like you’re out of things to talk about. But they also help you learn whether you’re interested in pursuing another date with someone. So as important as asking questions is, it’s equally important to listen to your date’s answers, and provide thoughtful opinions of your own. Don’t ask them all in one night! You don’t want the date to turn into an interview, but you do want to learn more about the other person. When you see an opportunity, ask a question.

Of course, not all of these first date questions will be appropriate for every situation. If your date seems uncomfortable talking about his or her family, no need to press the topic. If the conversation is steered toward dating history, and you feel comfortable asking about it, great! But if not, that’s fine too. Every date will be different.

The next time you’re on a date, work one or two of these dating questions into the conversation and see where it takes you!

Elizabeth Entenman

Freelance Writer

Elizabeth is a freelance writer, editor, and advertising copywriter in Brooklyn. Right now, she’s probably somewhere Instagramming her dogs.

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