31 Scarily Deep Questions You May Be Intimidated To Ask Your Partner (But Should Anyway)


Relationships can be tricky…I know, I know. Not only a Scrubs quote but also the most OBVIOUS statement to make ever. The thing about dating in the 20-teens is that it can be really difficult to REALLY get to know someone.

We’ve done it to ourselves.

Between Google, Social Media, Find Friends, Subtweeting and Subtexting, we’ve gotten to a place where we think we’re forming deep, long lasting connections, but oftentimes they’re actually superficial. We should be striving to make connections beyond emojis and lols, beyond what we can say in 140 characters or less, beyond what pops up when we type someone’s name into a search engine to see what we can find.

The next time you’re out with that person you say you want to get to know better, ask them something deep, something real. See what kind of a conversation happens. And if you don’t know where to start, maybe these 31 questions will help.


1. How many times did you change your mind about your career before you figured out what you really wanted to do?

2. Who are you closer with, your mom or your dad? Why do you think that is?

3. Who was the first person you ever loved?

4. What are five words you instinctually use to describe yourself?

5. What scares you the most about the future?

6. Do you think you’d make a good parent? Why or why not?

7. If/when you do become a parent, what is something you will take away from the way your parents raised you?

8. And what is something that you absolutely WON’T take away from the way you were raised?

9. Do you believe in heaven? Why or why not?

10. What is something you compromised on in a relationship that you wish you hadn’t?

11. What is something you refused to compromise about in a relationship that you wish you would have?

12. How would your best friends describe you?

13. What would your friends who you’ve grown apart from say about you?

14. Do you think love is something you can’t control, or something you choose to do?

15. Have you every cheated on someone?

16. What is your biggest fear about the future?

17. What makes you excited to get up in the morning?

18. What keeps you up at night?

19. What do you consider to be your biggest failure?

20. How do you handle your stress?

21. What holds you back from chasing things you really want?

22. What is something that scares you about yourself?

23. Which do you think is more important in a relationship, sexual compatibility or emotional compatibility?

24. Describe your worst/hardest break up.

25. Do you think we stay in love with some people forever?

26. Do you believe in staying friends with your exes? Why or why not?

27. Have you ever had to remove toxic people from your life? How did you do it?

28. Where do you go when you’re sad?

29. What is one of your biggest regrets?

30. Do you think we only get one soulmate in life, or several?

31. Do you think if younger you met you today, they’d be proud of who you are? Thought Catalog Logo Mark

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