The Great Date Experiment

“There is no such thing as a worthless conversation, provided you know what to listen for. And questions are the breath of life for a conversation.” ~ James Nathan Miller

I was fired up last Friday evening. My husband and I were sitting down together, enjoying a glass of wine, and sharing our days with each other. “I had the best day ever,” I exclaimed. When he asked why, and I started recounting my day filled with various meetings, I had a realization. It was a very full day starting with a breakfast meeting, a lunch meeting, an afternoon coffee meeting with several business calls in between (and no, I certainly wasn’t hungry after all of that!). I had driven all over town, and multitasked to get things done and keep focused. But, here it was, Friday evening after a long week, and I was totally energized.

My realization is that my day has been so energizing because it was filled with really great conversations. While none of my meetings were with any of my BFF’s, but rather all with colleagues and/or acquaintances, in every one of them we were able to get beyond talking about the weather, or how fast the year was passing, and instead get into really good conversations about life, our plans, our goals, our troubles, our fears. Instead of simply talking what we wanted to accomplish this year, we talked about our grandest dreams for our lives. Instead of just talking about what our kids were doing, we talked about what our kids are becoming. Instead of answering “fine” to the “how are you” question, we allowed our protective walls to come down and our vulnerability to surface. The conversations were honest. They made us connect. And, I left each one of those conversations energized, as opposed to sapped and drained.

Do you ever leave conversations, either with a good friend, a first date, or a casual colleague, and feel as if the conversation was pained and difficult? Do you feel like it never “clicked” and the two of you never connected? It’s draining, isn’t it? I did have a couple of these experiences lately (one with a good friend, and another with a professional colleague), and I couldn’t wait to escape.

Yes, escape is the best word I can come up with to describe that feeling of “I just need to get out of here right now as this isn’t going anywhere … I’m wasting my time … this surface conversation is going to drive me crazy!” I do (usually) try to rescue conversations when I feel them going this way, but sometimes they are unsalvageable. That’s when I start looking at my watch and tapping my toes. I begin to fidget and I know it’s time to leave.

My single friends who are in the dating world right now roll their eyes and laugh! They tell me they are, unfortunately, very familiar with feeling that need to “escape” from dull conversations. They know the “energy” that a great date with great conversation can bring. They know that feeling of dread that comes just a few minutes into a date when they realize that “it’s going to be a L-O-N-G dinner!”

What are you bringing to your dates? Are you bringing real conversation and dialogue? Or, can you be accused of sticking to mundane and safe topics, and not letting that wall of vulnerability and honesty come down? Do your dates leave feeling energized? Do they leave feeling like they just had a great conversation, or are they dull?

Here’s the Great Date Experiment: Next time you are out with someone on a date, instead of talking about the weather, or what he or she did that day, or what he or she has planned for tomorrow, or what sports his or her kids are playing this season, or how the Patriots won the Superbowl, try asking broader and deeper questions. Sure, get that basic Q&A out of the way, but then jump right in.

Ask things like:

  • What have you always wanted to try, but never been brave enough to do?
  • Tell me about the personalities of your kids.
  • If money were no object, what would you do for a living?
  • What keeps you up at night?
  • What do you want to be remembered for?
  • What is one of your favorite memories from your childhood?
  • If you could travel anywhere in the world, where would you go and why?
  • Tell me about the best book you have ever read.

“Conversation about the weather is the last refuge of the unimaginative.” ~ Oscar Wilde

Finally, be interested and be sincere. You may find you have absolutely nothing in common with this person. You may decide there is no need for you to have additional dates, and that’s OK. But, I can promise you that the date will be that much more interesting and energizing because you are sure to have learned something more than how your date hated the rain that day because it messed up his golf game!

What about you? What other questions do you ask to start a great conversation?

Monique-Honaman-2013-HRLT2About the Author:

Author Monique A. Honaman wrote “The High Road Has Less Traffic: honest advice on the path through love and divorce” (2010) in response to a need for a book that provided honest, real, and raw advice about how to survive and thrive through one of life’s toughest journeys, and “The High Road Has Less Traffic … and a better view” (2013) to provide perspectives on love, marriage, divorce and everything in between. The books are available on Learn more at

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