AoC Toolbox | How to Keep the Conversation Going (Episode 562)

The Art of Charm Podcast – Questions to Keep a Conversation Going (Episode 562)

The Art of Charm Podcast – Questions to Keep a Conversation Going (Episode 562)

The Art of Charm (@TheArtofCharm) has ways of making you talk! If you want to know how to keep a conversation going and avoid the awkward calm that sometimes besets even the most animated of chats, you’ll want to dip into the toolbox for this one. [Image of awkward conversation captured by Kyle Taylor]

The Cheat Sheet:

  • The best conversationalists are the best listeners.
  • The best questions to keep a conversation going with a girl
  • What do you do when you run out of things to say in a conversation?
  • Learn how to lessen the crushing pressure of being interesting by focusing on being interested.
  • Understand how to stay tuned in to the conversation by picking up on often-ignored (but crucially important) nonverbal cues.
  • Banish meaningless small talk and learn how to ask questions that build rapport and natural conversation.
  • And so much more…


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Have you ever found yourself in a conversation that just…stops? It’s awkward for everybody involved. Wouldn’t you like to be the person who can rally against the dreary lulls and keep a conversation going under any circumstance?

In this toolbox episode of The Art of Charm, Johnny, AJ, and Jordan show us how to apply AoC skills to the problem so we never run out of things to say — and never have to endure awkward pauses in conversation again. Enjoy!

More About This Show

Conversation, like dancing, is an art that ideally requires two or more participants (Joan of Arc and Billy Idol may be the respective exceptions to this rule). But what happens when we’re the ones who stumble over words that fall clumsily out of our mouths and regularly leave our partner with an awkward interruption in the flow?

We get better at conversation — and that’s where this toolbox episode of The Art of Charm aims to help. We even give you some questions to start a conversation with a girl.

Running out of things to say in conversation is one of the biggest problems we hear about from people who write in asking for advice. They may know how to initiate a conversation, but it’s how to keep the conversation going that gives them the most difficulty. They get to a certain point where the discussion just hits a dead end and neither participant is quite sure how to proceed.

Most of us can sympathize, because it’s happened to all of us. We understand what it’s like to get that nervous lump in the throat and the sweaty palms of being on the hook for contributing to the discussion but coming up blank. It’s a lot like how we felt in elementary school when the teacher would call on us to answer a question and cold panic washed over us as we realized we hadn’t been paying enough attention to even know what the question was.

At its core, the cause is similar — we lapse in knowing how to keep the conversation going because, on some level, we haven’t been paying attention.

“This problem really presents itself because we’re not listening,” says AJ. And all of the conversation cues happen on a verbal and nonverbal level. So when I say listening, I don’t just mean with your ears — I also mean with your eyes. We’re not paying attention to people’s facial expressions and the emotion that is coming through what they’re saying. So that’s what we really want to focus on: how to become a better listener. Because the best conversationalists we’ve met in our lives are incredible listeners and they find those ways to relate to you in a relatively easy fashion.”

Johnny adds to this by using a sports analogy.

“We all like to think we’re very good listeners and if we hear the right thing that we can have a witty, snappy comeback,” he says. “And the girl or whoever we’re speaking with is going to think we’re the most hilarious and amazing person on the planet. And so we’re always focusing on trying to hit the home run. So we ask a question and then we get a pitch coming in. And we don’t like that answer. We don’t have anything zingy [or] witty to go with that. So we ask another question. And we don’t like that answer. So we’re just standing over the batter’s box waiting to swing and waiting for the perfect soft pitch coming over the middle that we can smack a home run with.

“The thing is, it’s getting out of the thinking of trying to smack a home run and getting into the thinking of just getting on base — just getting a grounder. Just move the conversation along. Quit looking for the home run.”

Listen to this episode of The Art of Charm in its entirety to learn how we use improv to get us out of the habit of waiting for the perfect pitch and being present enough in the moment to roll spontaneously with whatever comes our way, what the conversation formula is and how to make sure we’re giving as much as we’re getting when conversing with someone we don’t know very well, what kind of whiskies Johnny and AJ prefer, how to test what you should be sharing in conversations (versus what might just bore people), why questions are great conversation starters, how to instill conversations with an enthusiastic and emotional impact, what emotional bids are and how their recognition is imperative to forming strong conversations that build meaningful relationships, and lots more.


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