The Key to Starting Amazing Conversations

I admire people who have the ability to ask good questions.

One time I was talking to a girl I had just met.  Out of no where she asked, “Are you in love?.” I paused. It was a much better question than asking, “Are you married?” or “Are you seeing anyone?.” Instead of a simple yes or no, her question made me to think.

So what’s a good question?

One that causes people to want to engage. Generic questions like, “How are you?” don’t really get a good conversation going. Most of the time when people ask how I’m doing, I reply with a simple, “I’m good!.” I know this, yet I continue to ask people the same. It’s a reflex, just like saying “hi.”

Whenever I remember to, I like to practice asking good questions. Some examples of questions I like:

“What’s your favorite part about your job?”

“What was the most profound moment of your trip?”

“What’s your favorite thing about your significant other?”

I also enjoy “How much…?” or “Would you rather?” questions.  These kind of questions are funny, make you think, and create bonding opportunity.

“How much would someone have to pay you to jump into a non heated pool right now and then take a cab home?” (asked in freezing weather).

“Would you rather eat a handful of dust from the vacuum cleaner or a wad of hair?”

Think about what kind of questions you can randomly ask to get a good conversation going.

This Post Has 3 Comments

  1. Alexandra

    Hey it’s me! 🙂 hehe.

    Always love your posts CC.

    Question: would you rather fight a hundred duck-sized horses. Or a horsed-sized duck?

  2. Christine C.

    Yes! I love that photo of you Alex.

    Hm. Both are pretty creepy. I’ll go with a hundred duck-sized horses. Then at least I can kick them.

  3. Margot

    …a handful of dust from the vacuum cleaner. 😉

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