Never have a boring date again: Ask powerful questions!

“We make our world significant by the courage of our questions and the depth of our answers” —Carl Sagan

Genuine curiosity is as SEXY as it is RARE. 

When was the last time you sat with someone who made you feel deeply SEEN? Unless you are extremely lucky, true empathy is not a common occurrence. 

As small children, we were naturally curious. We constantly asked questions of our parents, because we were not afraid of looking stupid, inadequate, or being rejected… yet.

Then a tragedy happened. As we became socialized and went to school, we learned to curb our natural curiosity. Asking the “wrong” questions at the “wrong” moment became a punishable offense both by adults and by our peers. Perhaps we got made fun of for asking so-called “dumb questions”; perhaps we got scolded because we spoke too much. Either way, we might have realized that we would be rewarded more for staying quiet than for asking questions. So, naturally, we shut down our true selves—our curious selves. 

Fast-forward to adulthood. We sit down at a cafe for a first date.  We start asking the typical, “How are you?—I’m fine”, “What do you do?—I’m an engineer. What about you?”

Snore. Why does this date feel so boring? This person seems cool enough, but we are clueless as to how to move this conversation beyond the surface.

Let’s start with the bad news: There will be many more boring dates in your future if you do nothing.

Now, rejoice for the good news: You can transform your next dates (and relationships!) into fun and engaging ones by re-harnessing the exuberant quality you were born with: GENUINE CURIOSITY!

The book “Ask Powerful Questions: Create conversations that matter” by Will Wise & Chad Littlefield is a wonderful place to learn about the secrets of meaningful conversations and deep connection. It’s definitely worth a thorough read! In the meantime, here’s some of that wisdom applied to how you can start elevating the quality of your dates today.

1.     Come to your date with the intention of curiosity. Put aside any expectation or self-consciousness. Set the clear intention to simply be curious—to take a tour into this person’s psyche, as if it were an exotic landscape. Do not try to figure out if they’re “the one”; this will take you away from the present moment. Instead, explore who they truly are. Bring your childlike curiosity to task, and shelf any worry about what they think of you, whether you want to see them again, or what will happen next. Simply focus on creating a space of trust, openness, and connection.

2.     Ask powerful, open-ended questions. Open-ended questions require your date to think in a fresh way rather than regurgitating a fact they already know—which is why they bring you right into the present experience. This is the space where REAL CONNECTION can happen! Here are some ways to turn close-ended questions into open-ended ones:

—> Ask questions that start with What and How.

Questions that start with Is/Are, When, Who, and Where are likely to elicit short, factual answers like yes or no, the name of a person, a date, a time, or a place. They do not invite personal reflection or creativity: instead, they keep conversations locked in the dry landscape of rehashed information. 

Consider the difference between, “When did you become a nurse?”, vs. “What compelled you to become a nurse?” The first question can be quickly answered with a number, say 10 years ago. It does nothing to lead the conversation into a territory of deep meaning. The second question, on the other hand, goes to the core of what motivated a person to choose a career in nursing, and is much more likely to result in an authentic moment of emotional intimacy. 

Here is another example. Consider the difference between “Where did you go to college?”, vs. “How did your college experience impact who you are now?” The first question is surface-level, while the second one requires introspection. Practice turning your typical first-date questions into open-ended ones, then watch your conversations transform.

Here is a cheat sheet of more open-ended date questions (many of which sourced from Will Wise & Chad Littlefield’s website):

-       What has been the highlight of your week (or month/year) so far?

-       What would you say are your top 3 values in life?

-       What is one of your favorite topics of conversation?

-       What are your hopes for what the future holds for you?

-       What has been your greatest accomplishment so far?

-       What is a talent or skill you have always wanted?

-       What is a goal you plan on accomplishing this year?

-       What is one thing you want to accomplish in your lifetime?

-       What is one thing life is teaching you right now?

-       How did you learn your most important lessons in life?

-       What is the hardest thing you’ve ever done? 

-       What is one thing or situation that scares you?

-       What is your dream?

-       Who are the most important people in your life, and why?

3.     Practice deep listening. Once you ask a powerful question, give the person your undivided attention as well as ample space to think and respond. Resist the temptation to interrupt, interject, or turn the conversation back to yourself. Let your conversation partner express themselves fully before asking a follow-up question or moving the conversation in a different direction.

Deep listening is a gift as much as it is a rare occurrence: it is the state of being that allows us to make another human being feel seen. In the words of theologian William Stringfellow, it is a primitive act of love. Deep listening is foundational to creating deep bonds of trust and intimacy, and conversations that leave us better than they found us.

If your date does not return the favor and starts dominating the conversation, tell them all about your newfound interest in creating meaningful communication, and excitedly invite them to practice asking powerful questions with you ;) They might thank you!

In conclusion, remember that your communication skills are more important now than ever, in the time of Covid-19 and shelter-in-place. Without physical contact to rely on, the success of your phone or videocall dates depends almost exclusively on your conversational abilities.

Furthermore, this skillset will serve you in every area of your life, from friendships, to business connections, to family relationships. This is also how we can each create a world based on empathy, connection, and understanding. There is literally no reason not to do this!

Please let me know how these tips work for you. If you’d like more personalized support, check out my coaching offerings and book a free 30-min consultation with me!

Warmly,

Marie xo