There is no one-rule-fits-all when starting conversations with people. There are different types of conversationalists, each with their pros & cons. Previously we examined Still Waters.

The second talker type is “The Jester”.

The Jester is often very fun to make conversation with. They find the lighter side of any topics, they make you laugh, they are very entertaining.

And if they are making you laugh, it is probably because they are taking the conversation in unexpected directions. Which is a treat if you have been having stale conversations.

The problem Jesters can have is letting a conversation get serious.

Jesters have an instinct for getting the laugh out of a situation. As such, they resort to this pattern even when a conversation is starting to go deeper. But at this point a joke can be a roadblock to a deeper conversation.

It’s not intentional, but they use jokes as a conversation defense rather than answer questions in a way that may leave them vulnerable.

At this point it might seem helpful to give a sympathetic laugh. But if you are asking them a genuine question that they have deflected, come back to it. Pursue the answer.

Vulnerability is the key to conversations that build connections. Having a few laughs is a good path to building friendships, but the jokes will be a dead-end if you never connect on a deeper level.

Perhaps it is self-imposed, but Jesters rarely have people take them seriously. If you can be that person to take them to a serious place, you might be able to be a unique friend for them. And they will be a fun friend to have too.

For Jesters, the challenge they face is that when they are ready to say something sincerely, people are expecting it to be a lead up to a gag. It becomes the way friends perceive you.

If you are the Jester, do your best not to deflect the serious conversations. People already like you, you just need to let them in.

Joke around, have some laughs. But don’t let it be the only side of you that people get to interact with.


You yourself may be the Jester if:

  • You are always looking for the comical angle of a conversation.
  • You would rather avoid conversations getting deep. It may even make you nervous.
  • When you say something serious, people wait for the punchline.