Do Your Conversations Fall Flat? Do a 180 by Fostering Intimacy.

Learning Objective: Who doesn't want to have better conversations? Rather than hitting a "banal ball back and forth", as comedian Pete Holmes says, learn the key techniques that will elevate your conversation skills and help you to be a better friend, networker, and maybe even fall in love.

Communication Listening
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Rise Above Banal Conversation

Bill Moyers once said that a benefit of being a journalist is learning in public. This relies on two important skills: An ability to ask good questions and the willingness to listen. Many of us want to be heard, but fewer want to spend time hearing what others have to say. Engaging in intimate, personal conversations requires that both parties truly listen to each other. Fortunately, that is a skill anyone can attain with patience and practice. A set of predetermined questions also helps, which we’ll provide in this Deep Dive. 

As Pete Holmes, comedian, actor, and host of the podcast You Made It Weird, says in his Big Think Edge lesson just below, implementing a safe space where the person you’re talking with is comfortable discussing anything on their mind is essential for creating the conditions for a great conversation. This happens when you practice non-judgment—the willingness to listen without prejudice—at the outset of the talk. By allowing the other person’s mind to roam freely, the chances of really getting to know them is possible. 

A free-roaming conversation does not imply that there are no boundaries, however. Understanding and establishing what the other person is unwilling to discuss is equally relevant. Of course, as Holmes mentions, there are ways of opening someone up without being manipulative. Artful interruption pushes the conversation forward, forcing the other person to abandon auto-pilot mode and truly think about their response. The result is a richer discussion in which both parties have an opportunity to learn something about the other. 

Some of us are natural talkers; others take prodding to pull out details. This is true in relationships and friendships, when speaking with strangers or with a person you’ve known for years. In every situation, the art of listening is paramount. The 36 questions that follow are perfect for acquiring this important skill. 

Being a good conversationalist requires listening more than speaking, which is a skill we can all practice to achieve better relationships⁠—or even fall in love.

More content in the full Deep Dive:

36 Questions Designed to Help You Fall in Love With Anyone

The Art of Active Listening

Co-Create a Better Relationship

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