Best Questions To Ask On a Date

30 Questions You NEED To Ask By The Third Date To Decide If There Should Be A Fourth

Just save everyone the time, take a risk and ask.


Seeing if you are compatible with someone is much harder than one would originally think. If you are an amicable enough person, getting along with people can be easy enough. You might get along with someone great but could never have a successful relationship with them.

Honestly, life is too short to be too scared to ask the hard questions. If you want to be dating this person, you should want to just dive right in, and get to know them. Some of these may seem like premature questions, and that you're concerned with scaring the person away—but I believe that if you are dating someone you should see a future with them, and why waste both of your guys' time if you aren't even on the same page?

This is something I have personally learned over the years since I am a pretty confrontational person. I will just go right in and ask someone a relatively intimate question, and if that person is uncomfortable, then right there I know we're probably not a good match. Even though everyone is different, communication is still very key in every relationship. Don't be afraid to ask some of the hard questions at the beginning of the relationship. If anything it will bring you both closer, or show you right off the bat that maybe you're not the best match.

Here are 30 of the best questions to ask on a date:

1. What's your best friends most redeeming quality?

2. If you had 24 hours to live, what would you do and who would you spend it with? 

3. What's the best piece of relationship advice that came from your parents/grandparents?

4. When was the last time you laughed so hard you couldn't breathe?

5. What what a big lesson you learned from your last relationship?

6. What does your ideal day look like?

7. Most awkward moment you had growing up?

8. What's a mistake you've made that later made you a better person?

9. Would you drop everything to go do something spontaneous and out of your comfort zone?

10. What's the most stupid thing you've done, that came with the best memories? 

11. What's your idea of a perfect date, start to finish?

12. If you're gonna drop a lot of money on something, what would it be on?

13. When/where do you feel most yourself?

14. What are you most scared for the future?

15. What are you most excited for in the future?

16. Do you see yourself having a family of your own one day?

17. How's your relationship with your family? 

18. What/who constantly drives you to be better? 

19. PDA? Yay or Nay? 

20. What's your dream job?

21. Are you alright with being uncomfortable?

22. Where's the craziest place you've done it?

23. How important is your alone time?

24. Where do you see yourself in 10 years?

25. Are you a morning or night time person?

26. Kids, love or hate?

28. If you could live anywhere, where would it be?

28. What's your biggest pet peeve?

29. What is the best time period in a person's life?

30. Dogs or cats? (This one's a deal breaker)

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