How do you deepen a conversation? originally appeared on Quora -- the knowledge sharing network where compelling questions are answered by people with unique insights.

Answer by Dan Chang, former shy guy, founder of TheFriendFormula.com, on Quora:

How do you deepen a conversation?

It's really simple. All you have to do is ask (and answer) a series of questions that get increasingly more personal.

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Over time, as two people share more personal information, they build a connection. The typical progression goes like this:

Cliches --> Facts --> Opinions --> Feelings

That's it. It's powerful stuff, though.

Several studies have shown that deepening conversations actually makes people like you more and stay your friend.

But most people tend to keep their conversations on the same level, and get stuck at cliches and facts. Like talking about the weather. Or the news. Or whatever they're comfortable with.

The key is really focusing on the transition from facts to opinions and feelings.

In other words, focus on moving from WHAT to WHY.

Get really good at asking questions.

Most people ask generic questions like "How are you?" or "What do you do?" and then they get a generic response. Specific questions will get more specific answers and move you away from cliches and facts and into the deeper stuff. This helps open up even reserved people because they see that you actually care.

So let's break it down.

Instead of asking the generic "How are you?", ask something just a little more specific, like "How's your day going so far?"

From there, continue asking specific questions to really understand their day:

  • What's going well? What isn't?
  • Doing anything fun?
  • Any plans for tonight?

And from there the conversation can go into a whole range of topics. I find people end up talking a lot about their jobs or their families.

In any case, continue asking questions that really draw on their opinions and feelings:

  • What's that like? It must be so exciting.
  • What's your favorite spot to eat around here?
  • Do you enjoy that?
  • Are you attracted to me? (Just kidding, don't do that!)

Here's to deeper, more meaningful conversations.

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