30 Telling Questions To Ask On A First Date

A first date is all about getting to know the other person and seeing if in the long run they will make a good partner for you. Dates can go bad really quickly if no one has anything to talk about or if someone talks a bit too much. The most successful dates happen when both parties talk equally and really make an effort to listen in conversations. While deep and meaningful conversations are what makes a relationship last, remember this is your first date and to keep things playful and light. The most important rule on a first date is to be yourself because you will want someone who accepts you for you and not a character you put on. Here are 30 telling questions to ask on a first date that are sure to help you learn more about someone.

The big questions

Here are 8 questions that are a bit more in depth and will really help you get to know your date. Make sure to space out some of these questions because you don’t want to overwhelm them.

1. What do you do for fun?

You want to make sure your date has their own hobbies and interests. This is a great way to find out more about them but also find ways to relate to them. Let’s say Jim were to say, “I love to run during my free time”, then Pam could say, “I love running too, we should go for a jog together.”


2. Do you travel a lot?

If you are a big traveler this is an important one to ask. Do you want a partner who can’t wait to jet set with you or someone who can’t even get on a plane without complaining? This question is also a good way to indirectly find out about their finances. If your date saves their money well odds are they travel a lot. While money is not the most important thing it is good to get a grasp on the finances of a future partner.


3. Are you competitive?

This is one you might not think is important but will eventually come up. You would rather find out that your partner is super competitive on the first date then a month in when you bring them home for family game night and they scare your entire family with the amount of passion they all of a sudden have for Monopoly.


4. What do you do with your friends?

This is a sneaky way to make sure your date has a social life. While having a partner that wants to spend time with you is great it is important to make sure they aren’t smothering you. If Jim says, “My friends and I usually go bowling. My one friend Michael is an awful bowler.”, this is a good sign that he has social skills and not a loner. But if Jim says, “I am busy with work a lot and just look forward to having a glass of wine at home alone.”, this might be a red flag.


5. What do you believe in spiritually?

This is an obvious one but can be difficult to phrase correctly. Use the words “spiritual” and “faith” instead of “religion” because you don’t know what they believe in and you do not want to assume they associate themselves with a religion. This question also allows you to decide if you need someone that shares a faith with you or if you are open to being with someone that has different beliefs.


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6. Do you have any future plans?

Make sure to ask this question with a big smile on your face because this is a big one. You want to know what your date plans to do with their life. If they are pursuing a career make sure that they have time to fit you in. And if they seem like they are ready to settle down make sure that you are ready to start thinking about next steps in your life. While it is great to be in the present it is also important to make sure you and your date could have a happy future together.


7. Are you an introvert or extrovert?

This is an important question to figure out how you will communicate with your date. Will they need more space or want to text you all the time? If you are an extrovert dating someone similar may be good because you know how to communicate with them but it could also be tiring because there is little down time with two extroverts. And if you are an introvert it could get bland dating someone else who is introverted as well. This is definitely a big and complicated question that you should consider heavily.

8. What’s your family like?

Family dictates a lot about a person. By finding out about your date’s family you end up learning a lot about them. You learn about their back story, how they were raised, but also what role models they have, their parents. If you see this date leading to something long lasting make sure you remember all the details they tell you about their family. Later when they bring up their aunt and you ask, “Linda or Kimmy?”, they will know you have been listening to them and will definitely appreciate you.

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The background info

Here are 12 questions to get to know the cold hard facts about your date. While basic these are awesome questions to understand your possible partner’s background.

9. What school did you go to?

10. What do you do for work?

11.  Do you have any siblings?

12. Do you speak any other languages?

13. Where do you align politically?

This one could also be considered a “big question” depending on how passionate you are about politics. While you and your date do not need to share every political belief it is definitely good to have common ground on a few big topics like: gay marriage, women’s health, and healthcare.

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14. Do you have any pets?

15. How do you stay healthy?

16. Do you drink?

17. Do you smoke?

18. How often do you see your family?

19. How often do you attend your church/mosque/synagogue?

Ask this one only if it applies.

20. Are you comfortable with PDA?

(Public displays of affection)


Here are 10 questions to find out what your date enjoys. These are more fun and lighthearted. If you are running out of things to talk about these are definitely a good way to spark a conversation.

21. What is your favorite book?

22. What is your favorite tv show?

23. What is your favorite movie?

24. What sports do you watch?

25. Do you prefer beer, wine, or hard liquor?

26. Do you prefer staying in or going out?

27. What’s your favorite place you have visited?

28. Do you prefer museums, theater, or opera?

29. Whats your favorite thing to wear on a date?

30. Would you choose winter, spring, summer, or autumn?


What are your favorite telling questions to ask on a first date? Comment below!
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Comments, Questions & Rants

Isabella Southwick

Isabella was born and raised in San Francisco but will be a member of the class of 2021 at the University of Kansas. She is majoring in political science and hopes to pursue a career in policy. She hopes to rush a sorority and cheer on the Jayhawks at every game.