50 Deep Questions To Ask Your Best Friend (To Get To Know Her Better)

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50 Deep Questions To Ask Your Best Friend (To Get To Know Her Better)

Your best friend is your partner in crime. She’s the one you know will be the Thelma to your Louise, and the Butch Cassidy to your Sundance Kid.

She’s your confidante, your ride-or-die, and the one who acts as an absorbent shoulder when that one guy breaks your heart.

You love her to pieces and know how to be a good friend to her, but even if you’ve known her for years, you might not know everything about her.

The more you know about your best friend, the more you will love her. It helps you two bond and can make a huge difference in the way you see one another. That’s just the way friendship goes!

Even if you’ve been friends since grade school, I’m willing to bet that these deep questions will help you know your BFF better.

So, here are 50 questions to ask your best friend that will strengthen your bond and bring you closer together.

RELATED: 100 Inspiring Friendship Quotes To Show Your Best Friends How Much You Love Them

1. Who was the worst boyfriend you ever had, in your opinion?

2. What’s your all-time favorite song?

3. What are you most afraid of?

4. Did you ever experience something paranormal? If so, what did you see?

5. If you could have dinner with any famous historical figure, who would it be and why?

6. What do you think is your biggest accomplishment today?

7. What did you first think when we met? Did you think we’d be friends this long?

8. If you could have the perfect day, what would it look like?

9. If you could have a “life redo,” what would you do differently knowing what you do now?

10. What was the greatest prank you’ve played on someone?

11. What’s your least favorite food, and why?

12. What do you think is my biggest fashion mistake?

13. Is there a smell that reminds you of me?

14. What are the first three laws you’d try to pass if you became president?

15. Which friend of yours impresses you the most? You’re not allowed to say me.

16. How do you comfort yourself after a terrible, horrible, no good, very bad day?

RELATED: How To Be A Good Friend & Create Friendships With An Unbreakable Bond

17. If you could be an animal, what would you be?

18. If you could hang out with any celebrity, dead or alive, on a regular basis, who would it be?

19. What do you think life will be like when we’re 85?

20. If we met earlier, do you think we’d still want to be friends? Or, do you think we’d be way too different?

21. Do you believe in reincarnation? Why or why not?

22. What was your favorite memory that you had at school?

23. Which family member do you feel closest to?

24. What was your most embarrassing memory?

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25. Let’s say you lived in a fantasy world. What mythical being do you think you’d be born as?

26. What superpower would you want to have?

27. Did you ever send someone a gift that they clearly hated? What happened?

28. Do you have a go-to dinner recipe you swear by when you want something tasty but impressive? What is it?

29. Which cartoon characters did you love as a kid? Which ones did you hate, and why?

30. Did you ever drop acid or have a hallucinogenic trip? What was it like?

31. Has anyone ever mistaken you for someone else, only to do something they regretted because of it?

32. If you could pick an age to stop aging at, what age would you want to stay? Why?

33. What’s the weirdest thing you’ve ever bet on? Did you win the bet?

34. What would you do if your significant other didn’t want to work anymore, and expected you to support them?

RELATED: 10 Signs You Have A Truly Genuine Friendship

35. Do you have any recurring dreams?

36. If past lives exist, what do you think your past life was?

37. What’s a little-known skill you have?

38. If you could live anyone’s life for a week, who would it be?

39. What’s a skill you’ve always wished you had, but never quite managed to get a hang of?

40. Is there a cartoon character you can really relate to? Who is it, and why?

41. What time period would you live in, if you could live in any time?

42. You just found out that you’re a distant relative to royalty, and you now have a royal title. What title would you want, and what country would you want to represent?

43. What’s your opinion on couples’ costumes, for costume parties? Do you think it’s overkill, or adorable?

44. What emotion do you feel you experience the most?

45. What’s the one aspect of a guy’s personality that is either an immediate turn-on, or turn-off?

46. So far this year, what do you think was your best moment?

47. Were there any careers that you almost pursued, only to change your mind at the last minute or just have it not pan out? What happened? Do you regret it?

48. If you could do anything for the rest of your life, what would it be and why?

49. Do you have any advice for me that you’ve been wanting to tell me, but haven’t gotten around to saying it quite yet?

50. Who’s your favorite reality TV star?

RELATED: I'm Closer To My Best Friend Than I Am To My Partner Of 15 Years

Ossiana Tepfenhart is a writer based out of Red Bank, New Jersey. She writes primarily about lifestyle, food, finance, and relationships. You can follow her Twitter.