A good way of getting the conversation flowing in interesting & creative directions is to play a conversation game.
Awkward Silence have invented a conversation game called “The Last Time”.
The concept is simple. Ask whoever you are with when the last time they did something was, and get an insight into their life.
“When was the last time you felt excited?”
“When was the last time you apologised to someone?”
“When was the last time you went on a water slide?”
“When was the last time you lied?”
“When was the last time you made a new friend?”
“When was the last time you did something for the first time?”
“When was the last time you cried?”
Obviously don’t just answer with a day or time, get the story accompanying it.
A variation on this is asking about first times.
"When was the first time you drove a car?"
"When was the first time you kissed someone?"
"What was your first impression of me?"
"What was the first time you left the country?"
Once the creative juices get flowing, you will learn quite a lot about each other.
Try something more than mere courtesy. Taking a comment beyond what is expected demonstrates sincerity.
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If you aren’t listening, the conversation doesn’t evolve. It’s just two people saying things they each already know at each other.
Some things are good for us to hear, even if they are things we already know.