20 Questions

How many of you have played 20 Questions? It’s a simple game of deductive reasoning that I’m sure most of you have heard of. One person chooses a subject/object and the other person has 20 yes/no questions to ask to figure it out.

It is NOT what this post is about, however. Because, why make sense when I can confuse you with a title and then go on to a loosely related topic?

brown ostrich
If this is you right now, I understand. I’m irritated with me too. 😉
Photo by Adriaan Greyling on Pexels.com

Friday night, I was chatting with a colleague who has transitioned into the friend zone. To be more specific, she and I are quickly becoming long-distance besties. She lives in Mexico. I….do not. We’d had a long work week and so decided to shift from work banter to sharing some virtual drinks and playing a game. We tried to play Rummikub with my mom online – to no avail. So, I suggested 20 Questions and asked her if she wanted to play the real game or one that I made up and which was purely designed to be nosy. She chose the latter because….bestie (duh).

What followed was a “brief” 3.5 hour WhatsApp chat that was the most candid and heartfelt interaction with a human being that I have had in a long time. We were actually only able to get in 16 questions before I had to call it quits because I’m old. That’s not true but I do like to go to bed early and honestly, I wanted to save some questions so we could chat more later.

We talked about heartbreak, loss, love, fears…you name it. There was no hesitation or embarrassment. Just two friends in a lightning round of “let’s get to know each other”. It was fabulous. I was surprised with her willingness to share such personal details about her life but I don’t know why that came as a surprise. The universe brought us together and we often joke about being each other’s spirit animals. We are opposite sides of the same coin. She’s the peso to my penny, you might say. It makes sense that we’d be so willing to share our hopes, dreams, and disappointments. That’s what friends do.

I guess because I spent so many years keeping people at arms length, it can still be jolting (in a good way) when I forge a real connection. I am so grateful for these moments…these friendships. All of it.

So, I thought I’d share some of the questions we asked each other as well as some I’d still like to ask to round out the…

Top 20 Questions to Ask a Friend

  1. What embarrasses you most or has been your most embarrassing moment?
  2. What was your best/worst experience with alcohol?
  3. What’s your biggest fear?
  4. What’s your biggest fear that has come true?
  5. Who’s the last person that made you cry and why?
  6. What’s one thing that most people don’t know about you?
  7. When do you get frustrated with me? Or, what frustrates you about me?
  8. Do you believe in aliens or ghosts? Why/Why not?
  9. What three words would your friends use to describe you?
  10. Do you believe in soulmates?
  11. What are your phobias?
  12. What do you regret the most?
  13. Why did your last relationship end?
  14. What are you worried about right now?
  15. Who is your hero?
  16. What is your proudest accomplishment?
  17. What is your favorite book/movie/song?
  18. If you could go back in time and change one thing, what would it be?
  19. What’s your favorite childhood memory?
  20. What’s the most unusual thing you’ve ever eaten?

I’m sure there are HUNDREDS more that would be great to add to this list. What questions would you ask your BFF or a friend you’re trying to get to know better? Gimme all ya got! 😉


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