The #1 Dating Skill!

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To say that a person feels listened to means a lot more than their ideas get heard.

It’s a sign of respect. It makes people feel valued.”

Deborah Tannan, Author, You Just Don’t Understand: Women and Men in Conversation



After my divorce, following almost twenty-five years of marriage, I never planned to date. But in her endearing, sassy way, my 18-year-old daughter was my first encourager. “C’mom, mom,” she said. “You need to find someone to love you before you get too old!”

I had been having weekly conversations with a therapist about how to be open to the possibility of my life looking different. But dating…not so much. Why was I afraid, he asked?

Why? Because it had been YEARS. To say I was rusty was an understatement.  I could scarcely remember what you did on a date.

And then my therapist said the words that got me thinking:

“What you do on a date is what you do every day: you talk and you listen. Wash, rinse, and repeat.”

And, he went on: “You are an excellent conversationalist because you make others feel cared for.”

Now, he had me curious. “How do I do that?”

“Easy,” he answered. “You ask questions, and you pay attention to the answers. Being able to listen with interest is the only dating skill you’ll ever need. The rest will fall into place.”


Surprising both my daughter and me, I have been on a LOT of dates since my divorce five years ago. How many? Let’s just say double the number of years I have been alive! And that number puts me squarely above the half century mark.

I have met both wonderful and not so wonderful men, made memories, had iconic New York City experiences, but most of all LISTENED. My curiosity about the men I have dated is sincere.

Here are three listening tips to have the best dating conversations:

  • Ask questions that allow your date’s story to unfold and expand. One of the most commonplace kick starter questions we all ask is what a person does for a living. But then ask the next question after that: How did you get started? And then ask the next question after that: What do you love about what you do?
  • Listen to what’s being said, as well as what’s not being said. Let’s say your date works in a family business. Let’s also say your date indicates he joined that family business right out of college. Ask him if there was another path he thought about taking. And then listen to the response. It’s called “listening between the lines”.
  • Reference what you have learned from listening to move the conversation forward. Being able to build on what you hear requires your complete attention. You must be fully present in order to take the information that is shared, and add to it.


One of the best compliments I have ever received came from Sam, one of the 15 men whose stories I tell in my book Mom…You Just Need to Get Laid: The Adventures of Dating after Divorce. After our first date, he called me to say thanks and to ask me out again.

“You know what I like most about you,” he asked. “You make talking fun!”

Sam went on to tell me that he was usually reticent to offer details about his life or to engage in a deep conversation on a date. “With you, it’s different. I don’t feel judged,” Sam told me.

Fear of what someone else will think is often what keeps us from speaking up, or being ourselves. When you listen unconditionally and without judgment, you allow the speaker to trust you.

I wish for you many interesting conversations, where you listen and are listened to. Dating will be much more rewarding if you value being a good listener. It’s offering the best part of you to open up the best part of your date.

As always, I’d love to know if this advice resonates with you. Write to me with your comments and questions at



  • Kate Somerset

    Kate Somerset is an author pen name for the book “Mom…You Just Need to Get Laid: The Adventures of Dating After Divorce”. Following a divorce after 24 years of marriage, and thirty years of being deeply rooted in professional and volunteer roles in Texas, Kate took a chance on a new life in New York City. She immediately fell in love with Manhattan and the many opportunities it offers. Kate’s book about 15 true dating experiences in New York City is an honest, humorous, and inspirational look on how to give yourself and romance a second chance. One of the most universal struggles faced by all of us – building effective social connections – is the focus of Kate’s monthly column for The Three Tomatoes. Published by Brooklyn Writer’s Press, the book and Ebook are available on Amazon. An audiobook produced by The Three Tomatoes is on Amazon and Audible. Learn more about Kate at

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