Nate Anglin

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How To Ask Unique Questions To Spark Memorable Conversations

We are overwhelmed with stupid conversations. 

"Hi, how are you?" 

"How's the weather." 

Shoot me!

They're easy to ask and make for a quick conversation. 

Get in, get out, my preferred introvert style. 

Nobody is interested in answering these questions. 

The weather is excellent, Nate. The Cumulus clouds were incredible yesterday. Do you see the pattern of the Cirrostratus, today? They were Magnificent.

I love teasing you winter people. 

It tickles my insides when I ask you, so, how's the weather and know you're going reply with a temperature I can't fathom living in.

I go into hypothermia at 60 degrees.

When people reply with their ridiculously cold temperature, I love to say, 

"wow, that's cold, and I thought today's high of 85 was going to be a tough day here in Florida. I may go to the beach if it gets warmer."

This leads to a decent conversation after a quick laugh. 

Instead, of how's the weather, what if I asked, "have you ever ran in the snow naked?"

Who's not curious about that? 

And if they did, why? What was the outcome? 

That would make a funny story. 

To have better conversations, we need to ask better questions. 

Here' a few ways you can ask better questions and my list of to ask strangers and spark memorable conversation. 

A few quick tips on asking unique questions

Ask positive questions only. This isn't a time for negativity. You don't want to walk up to a stranger and say, nice to meet you, has anyone you knew died from the Coronavirus? 

Asking different questions is to spark memorable conversations. Not be terrified of them. 

Actively listen when you ask a question, don't sit there twiddling your thumbs anticipating the next question. 

Be apart of the conversation. Smile, acknowledge them, and listen. 

Be open to what they say.  Stereotypes and negative judgment aren't allowed. Being shocked at their reply is permitted. 

If someone says, I live in a nudist colony, follow-up the answer with, wow, how did you end up there? Or, do you feel uncomfortable having your junk always wave in the wind? 

Be risky. Don't play your questions safely. The goal is to start meaningful conversations. With your risky questions, you still need to be respectful. Don't be a jerk. 

Follow-up the answer with more questions. Don't stop the conversation at their response. Dig deep into their reply. 

Here's a list of…

Questions I'm asking strangers

  1. What's the one food you can't stand to eat? 

  2. How many times do you wear that outfit before you wash it?

  3. What book have you recently read and got lost in? 

  4. If you could have dinner with anyone from history, who would it be? 

  5. If you could only speak one word today, what would you say? 

  6. What would be harder for you to give up: coffee or alcohol? 

  7. How many chickens would it take to kill an elephant?

  8. If you could lock up one person in a mental institution, who would it be?

  9. Would you rather live in a roller coaster park or a zoo?

  10. Would you rather hang glide or whitewater raft?

Let's start asking better questions and have more memorable conversations.