40 First Date Questions That Are Foolproof

What are first dates for? Sometimes people think they’re just meant to have a good time but in reality, you’re supposed to be getting to know the other person on a deeper level. You’re supposed to be determining if they seem like someone you want to go on a second or possibly third date with.

You’re not supposed to just go out, kick butt at mini golf, and then walk away not learning anything new about a person. Yes, you should definitely make sure to keep the date light and fun, but you also need to remember that you’re supposed to be asking questions.

But you can’t just ask any questions, right? You don’t want to make it seem like an interview! That’s not fun for anyone. We’ve put together a list of first date question that are foolproof.

Getting to Know Them

You can’t just go into a date and fire off a bunch of different questions. You have to warm up a little bit and get them open to talking with you. These are the basic questions you should always be asking on the first date – if not before.

1. What do you do for fun?
2. What is the most fun you’ve ever had doing something?
3. What do you do for a living?
4. Do you enjoy your job or would you like to be doing something else?
5. What were you like as a kid?
6. Where are you originally from?
7. Why did you leave there OR (if they haven’t left) Do you plan to leave someday?
8. Do you prefer TV shows or a good movie?
9. What types of shows/movies do you like most?
10. Are you into music?
11. What type of music do you listen to?

Getting a Little Deeper

Now that you’ve hit a few surface-level questions, you should start asking more questions that will tell you about their personality and their qualities. These questions aim to tell you a lot about who they are without actually digging too deep to make it uncomfortable.

12. Have you read any good books lately?
13. Why do you like to read books?
14. Have you traveled anywhere cool lately?
15. Do you want to travel somewhere really cool soon?
16. Are you more of a cat person or a dog person?
17. If you were only allowed to eat one food for the rest of your life, what would it be?
18. Did you have any funny nicknames growing up?
19. Do you have a nickname right now that people use more than your real name?

Dig a Little and Get Comfortable

This is the good stuff. These questions will open the doors for a lot more meaningful conversations and it’ll tell you an awful lot about who they are. Just remember to tread lightly until it seems like they are really open to discussing these things.

20. Were you bullied as a kid? What for?
21. How big is your family?
22. Do you get along with your siblings well?
23. If you won the lottery, what would you do with the money?
24. If you could be someone else for a day, who would you be and why?
25. If you could meet someone, dead or alive, who would it be?
26. Do you have any crazy pet peeves?
27. Are you a coffee or a tea person?
28. Would you ever pack up all your belongings and just move somewhere else at the drop of a hat?

The Important Stuff

These are all of the things you should take away after a first date and think hard about. These characteristics can help you see just how compatible someone is with you and your long-term goals and dreams.

29. Are you a morning person or a night owl?
30. Do you cook often?
31. What’s the one thing you want to accomplish before you die?
32. How big is your friend group?
33. Where do you see yourself in 5 years?
34. If you had to describe yourself in three words, what would they be?
35. When is your birthday?
36. What’s one thing you wish you could improve upon in your life right now?

The Wind Up

Now it’s time to wind up the date and start asking the questions that’ll set you up for a second date – assuming everything went well. These are always questions to make sure you ask at the end of a date when you had a great time and want to do it again.

37. How’s work looking for you this week?
38. Are you doing anything fun this weekend?
39. Did you have a good time tonight?
40. When are we doing this again?

Tips for a Smooth Conversation

It’s easy to slip into “interview” mode when you’re talking with someone on a first date. You definitely want to get these questions answered, but you have to do so in a way that seems natural and fun. Nobody wants to go on a date expecting a fun time only to be interviewed like they’re applying for a job. These tips can help with that.

1. Read their body language.

Not everyone is open to talk about the really important stuff right away. You have to gauge their body language and see if they’re open to you or shying away from a specific topic.

2. Let the conversation wander if it wants to.

If you two start going off on a rant about a certain question you asked, let it go. Don’t feel forced to get back to asking questions if the conversation is going in a good, natural direction.

3. Don’t worry about getting through the list so much as listening to their answers.

There’s no point in asking so many questions if you’re not fully absorbing what they’re saying. You want to make sure to get some questions answered, but don’t just go through the list without actually hearing them.

First dates aren’t supposed to be difficult, but you also want to make sure you’re getting to know the person you’re with. These question will definitely help with that.

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