Whenever you go out on a first date with someone the butterflies are going to stir up in your stomach and you are going to worry about all kinds of things.

If you plan it right, conversation doesn’t have to be one of those things. Sometimes finding something smart or timely to say can be hard, even for the most experienced daters of us.

But, because we’ve all been there and we know that getting tongue-tied is not that hard when you are on a first date, here are 40 questions you can use to guide your conversation.

Mix and match and pull them out as you need to so you can learn about your date and have a great conversation too!

The essential 10 first date questions you MUST start with

1) Are you working on any personal projects right now?

This is an excellent question to break the ice and lift the mood. If they’re working on something they’re passionate about, they’ll be very happy to open up about it.

If you’re interested in what they’re saying, the conversation will be effortless. They’ll be glowing and feeling good and this will set the tone for a great date ahead.

2) What does a usual day look like for you?

It’s boring when you simply ask, “what do you do?”

By getting them to talk about what they actually do during the day, not only will learn what they really to do, their answer will be so much more interesting for them to talk about because it’s not a question they’d receive very often.

3) What’s the last book you read?

You’ll learn a lot from this question. What people choose to read in their free time says a lot about who they are and what they’re interested in.

Most people are usually happy to open up about this kind of stuff and it can lead the conversation down a fascinating path.

4) Is there anything you don’t eat?

This ones an easy question to ask, especially if you’re on a dinner date. People usually have a story about why they don’t eat certain foods.



If they tell you what food they don’t eat, follow up by asking them why and what happens to them when they eat it. It will probably lead to an interesting reason and discussion.

5) What’s been your best vacation ever?

People LOVE talking about holidays where they had ample fun. It reminds them of good times which will spark the feeling to a passionate high.

Ask questions about the holiday to really keep the fun conversation going.

6) What’s the most surprising thing that’s happened to you in the past week?

It’s pretty boring when you simply ask, “how has your week been?”

This will instead lead you down a path that’s pretty interesting as it will force them think on the spot about the most interesting or surprising thing that’s happened to them all week.

7) What’s the best advice anyone ever gave you?

This will bring up some fascinating topics and they’ll be very forthcoming in telling you why it’s great advice. And learning some wisdom never hurt anyone 😉

8) What are your closest friends like?

People love talking about their friends. After all, there’s reason they’ve chosen them as their good friends.

They’ll usually have funny stories about them too so probe them more on this question wherever you can.

9) What were you like as a kid?

This is a surprising question to ask and most people will be happy to open up about it. You’ll learn more about them and what they’re truly like as a person.



10) What’s your favorite TV show ever?

This is a great one because TV is an essential part of nearly everyone’s life. Most people have a TV show that they absolutely love so it will lead the conversation down a passionate path.

BONUS: 40 first date questions to ignite the spark

  1. Where did you go to school?
  2. Where do you call home?
  3. When was the last time you traveled?
  4. Where did you go?
  5. What was the best part of highschool?
  6. How long have been living in the area?
  7. Did you go to college?
  8. What is your favorite movie?
  9. What is the worst movie you’ve ever seen?
  10. Have you ever gone to the movies on your own?
  11. What part of town do you live in?
  12. What do you do for fun?
  13. What’s the best show on television right now?
  14. Do you like reading?
  15. What’s your favorite band?
  16. Have you ever dropped a class?
  17. Are you traveling soon?
  18. What do you like about your boss?
  19. Have you ever thought of starting a business?
  20. What is your favorite food?
  21. Did you have a nickname when you were a kid?
  22. Do you have any pets?
  23. Are you close with your family?
  24. If you could spend a day with anyone, who would it be?
  25. What’s one thing that drives you crazy about people?
  26. Do you like coffee or tea?
  27. Have you ever been to Disney World?
  28. If you could live anywhere, where would you live?
  29. Trump or Bust?
  30. What’s something on your bucketlist?
  31. When was the last time you checked something off your bucketlist?
  32. Do you prefer mornings or evenings?
  33. Do you like to cook?
  34. What’s the worst job you ever had?
  35. Do you like parties or small gatherings?
  36. Do you take work home with you?
  37. What’s the funniest joke you’ve ever heard?
  38. What’s your work look like this week?
  39. Did you enjoy your meal?
  40. When is your birthday?

How to use these questions for maximum effect

A couple bonding. Signs he respects you.

The trick to creating engaging conversation is to get a good give-and-take momentum going.

Ask questions, let your date ask you questions, and try to be as honest as possible. You don’t need to give away the farm, but if your date asks you questions like these and you’d like the answers in return, be sure to answer them as best you can.

In fact, think of how you might answer these questions yourself before you pose them to someone else. Don’t ask any questions you wouldn’t want to answer.

Be sure to ask probing questions to learn more about a particular area of someone’s life.

For example, you can bundle these questions together and learn more about your date. Start with questions such as, “how long have you lived here” and add on, “where did you live before”, and then try, “which one do you prefer?” And your conversation will flow naturally from there.

While you shouldn’t expect to learn everything about one another in one night, it is a good chance to get to know someone better.

And if you have more questions, it’s a great way to prompt them for another date. Saying things like, “I’d love to learn more about your job or hobbies” and then ask for a second date.

It doesn’t have to be complicated and we humans are really good at making things complicated. So keep it simple.

When you head out on a date, be sure to pace yourself. Don’t bombard your date with 40 questions right off the top!

If it’s a good date, you’ll likely get to more than 40 questions naturally, but don’t force it.

If the conversation isn’t flowing, it’s no one’s fault. You just might need some time to get to know each other’s rhythms and the best way to do that is talk, talk and talk some more.

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