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Is it possible to teach yourself how to be funny?
And if so, how?
psychology
advice
Compesh is a question and answer (and debate) website, so before you make a debate, you better learn what an assertion is. I suppose you already know what a question is, and that you've typed it in the box. ;)
An assertion, is basically a statement you can make, that is either true or false.
Richer people have better health.
The question for that would be, Do richer people have better health?
And don't forget to make your assertion, match your question.
Also that there's different types of humour, makes it even more difficult. The humour I have is surprisingly cynical and outlandish. Another funny person will be good at satire or knowing what actions to do at what times. As funny people you meet aren't funny in the same way, it would be extremely difficult for you to learn from both of them at once if you tried. There are no examples for you to really learn off. At least with overcoming shyness and positivity, we know many people who are like that to compare off and get a standard.
Update
I've read Will Wister's answer, and he suggests that people should enter situations where they are supposed to be funny, such as practising to be a comedian, or being a writer.Why do you have to practise performing a role that is challenging? Why not make the most of the environment you have around you.
Could you be funny around other people in conversation, or even here, on Quora?
I've got a board on Quora called Funny Answers, and if you look at it, you'll find that I've posted the most funny answers on this site.
Funny Answers
If you really want to be funny, you should make the most of what's around you; so that your humour feels natural and not contrived. You should adapt the way you think to give a slant, so that you become a funnier person in your own right, rather than to try to do an art that you're not ready for yet.
We all have abilities to do certain things, but we have to learn the techniques before we can become skilled at it.
2019 Update
There are four elements to telling a good joke.