37 First-Date Questions to Ask When You Find Yourself Tongue-Tied

Updated 06/01/19
couple holding hands together
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First dates can be totally enjoyable, a so-so experience, or can leave you wishing you were anywhere else. (Remember that one time when your date handed you cash at the end of the night saying you could "get the points?") And just as every first meeting ranges from sweet to bizarre, so, too, do the first-date questions.

If you’re going on a first date, you may be a bit nervous about what you’re going to discuss. After all, what if there’s an awkward silence? What if the conversation lags? What should you even talk about?

By asking the right questions, you can share about yourself and learn valuable information about your date—things that will help you determine if you want to continue dating or not.

We asked around to see the questions our friends and co-workers have asked, been asked, and wished they'd never heard altogether. Ranging from corny to sincere to just a little bit strange, we've rounded up some of our favorite first-date questions. Scroll through, and keep some in your back pocket as conversation starters, and vow you'll never use the others.

Travel Questions

If you’re on a first date, talking about travel is a great way to keep the conversation moving and the sparks flying. After all, this gives you both the opportunity to share stories about your past trips, vacation experiences and favorite travel buddies, but you can also discuss your ideal travel destinations and the places that are at the top of your must-see list.

1. Have you ever traveled solo? How was it?

2. If you could live anywhere in the world, where would it be?

3. What are the five top travel destinations on your bucket list?

4. Is there a city you'd consider your home away from home?

5. What's the weirdest thing you've ever witnessed on public transportation?

Questions About Their Interests and Taste

Important questions to ask on a first date pertain to your date’s interests and preferences. Do they practice yoga, go hiking, or play tennis? Are they in a band or love to hit up local karaoke bars? By asking about your date's free-time activities and general interests, you can learn about their priorities as well as share about your own passions and pursuits.

6. How do you spend your Saturday nights?

7. What's the last book you read, and what did you think of it?

8. Sweet or savory?

9. If you could meet anyone, dead or alive, who would you meet?

10. Astrology: yes or no?

11. Aliens—are they real?

12. Paperback or e-reader?

13. What would your death row meal be?

14. What Starburst flavor would you be?

15. What time do you usually go to bed?

16. Breakfast, lunch, dinner, or brunch?

17. If you could have any superpower, what would it be?

18. Lounge on the beach or hit the slopes?

19. What bands/songs would make up the soundtrack of your life?

Questions About Their Career and Life Goals

When it comes to asking questions about your date’s profession and dreams, it’s important to ask a question that paints you as a positive person. In fact, since there are some people who don’t totally enjoy what they do, this approach can keep the conversation happy and upbeat, even if your date isn’t totally enamored with his or her work or work environment, but still has goals.

20. Where do you see yourself in five years?

21. What's one thing that scares you?

22. What's one thing you want to do before you die?

23. How would you like to be remembered?

Questions About Their (and Your) Past

If you want to dig a little deeper and open the door to share about the past, be prepared to share about your own. Questions ranging from your love life to your childhood can give you both an opportunity to share funny stories and interesting anecdotes about your life, and help you to better see where the other person is coming from.

24. How long was your last serious relationship?

25. What was/is your parents' relationship like? Would you aspire for your relationship to be like theirs? Why or why not?

26. If you were going to describe your love life using a book or movie, which would you choose?

27. Theoretically, if you had a past life, what were you doing in said past life?

28. Do you like your name? Did you like it when you were growing up?

29. If your friends were going to describe you using one word, what would it be?

30. What was your favorite childhood party theme?

31. What’s your favorite restaurant in your city?

32. How many siblings do you have? Are you close to your family?

33. What was the first concert you ever went to?

34. What were you like in high school?

35. What was your biggest childhood fear?

36. What is your favorite childhood memory?

37. Is your heart one that needs to be cracked or melted?

Do you have a favorite first-date question you like to ask? Up next: relationship compatibility based on zodaic signs.

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