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.
Who are your special people, the ones who will be there for you in both good times & bad?
Are you interacting through text, messenger & email rather than vocally? Is that even a bad thing?
Food should always taste better than it looks. Likewise, people should always be more interesting than they appear.
How we start a conversation often decides its trajectory. So maybe you should rethink how you greet people.
Even when you can't solve a friend's problem, talking about it helps.
Conversation will make or break a first date. How can you take the pressure off of thinking of things to talk about?
Do you use your words to make a positive impact or a negative one? Have you listened to yourself lately?
What should you talk about when you know a conversation is only going to be brief?
If you want to have a rewarding conversation with someone, never ask this question.
There is a reason we are social. It's to be known.