Having a good sense of humour makes you more enjoyable to be around. You might also do better at work (as long as you don't go overboard). If you were cursed with poor timing or a lack of the funnies, here's how you can develop your sense of humour.
Immerse Yourself in Humour
You learn more effectively when you immerse yourself in a subject (such as a language). Similarly, you can refine your sense of humour by immersing yourself in humour. Watch standup comedians. Listen to podcasts that amuse you. Read humorous books. There's a lot of funny out there!
For one thing, you might be able to actually copy the jokes and use them yourself. Benjamin Errett, author of Elements of Wit, says in an interview with Vice, "There are two types of people. Parrots and magpies. Some people just steal their lines, and repeat them. Others hunt out gold."
Although parroting is frowned upon in the professional standup comedy world (although it still happens regularly), there's no shame in regular folk parroting the pros, especially if you can use it as a stepping stone to evolve further. Even author Oscar Wilde was a parrot. Errett says in this interview with NPR:
He's an interesting case because a lot of what he's done was lifted and borrowed and recycled. You can even see in some of his most famous works, there are lines that reappear. So he was always honing and fine-tuning everything that he was doing. And one of the interesting things about him that I really find admirable is that he had this persona in sort of salon society in Victorian London as this guy who was a great talker, but what has he ever done? And he was sort of known in society - he was sort of a Kardashian of his time. But he went on to do works of great substance and lasting value.
If you're not particularly funny, you might start off as a parrot ("I heard something funny the other day…"). Immersing yourself in humour will definitely help you parrot away. However, if you want to evolve from parroting, don't just memorize or recite jokes. Pay attention to comedians' timing and delivery. Notice their facial expressions and body language. You don't have to replicate it, but you should notice it so you can use it in your own jokes.
Part of this process will be conscious, but your mirror neurons will probably pick up on certain cues and body language. For me, I find Aziz Ansari pretty funny (some folks prefer him in small dosages, but I could watch his standup for hours). I didn't even notice I was parroting his high-pitched voice until a friend pointed it out.
Be Witty, Not Silly
If you're looking to get wittier on the fly, as Errett highlights to the Wall Street Journal, your goal is to combine spontaneous creativity with ideas that delight. Sarcasm and stale jokes do have a certain funny appeal, but being witty goes beyond that.
The happy point is that if you don't feel like you're witty, you can develop wit. In that same interview with Vice, Errett says "George Bernard Shaw was originally a terrible speaker and about as sharp as a beach pebble, yet over time he worked on it and developed into one of the great wits of his day. Half the battle is accepting that you can learn it." In other words, you'll need to adopt a growth mindset.
The challenge of wit is in its spontaneity. You can hone your wit by regularly quipping with other people. If you know someone who takes being witty as seriously as you do, it might help to enlist them as a type of "witty" sparring partner.
If you're comfortable with it, you can also try your hand at wit in the real world (dinner parties, the office, the cafe, in the lift, family reunions). Part of this real world exposure is in exposing yourself to the spontaneity that wit requires. If you're new to it, or nervous or reserved about it, you might have trouble speaking up quickly enough to time it properly.
Silly humour can be a solid starting point for some audiences, but it can get old quickly. It also might make you look immature (which can be bad at work and in the eyes of some people). A lot of people laughed at Borat, not with him. (Plus, do you want to be known in the same context as Borat?) On the flip side, even bad comedy and silliness has its fans. Know your audience.
Learn What Amuses You
A lot of times, we say things purely to please others. We flatter friends or colleagues by praising a change they made. We bring up topics that we know others might be interested in. However, when it comes to being funny, don't tweak your sense of humour to cater to other people. Instead, start with what amuses you. Then, if you think the other person will also be amused with it, share it with them.
Will Wister writes at Quora:
When delivering comedy professionally or making friends laugh, it's important that you amuse yourself, and that you're not kow-towing to others with your humour. That's often deemed in the world of comedians to be the behaviour of a hack.
You'll be funniest when you find something amusing and delightful. That is the starting point, before you wonder about other people's opinions.
With that said, even though you're looking at your own sense of humour, you should definitely consider your audience and the situation. Even if a remark is absolutely tear-jerking, knee-slapping, hilarious, it can be considered in poor taste if you say it in the wrong situation. This type of observation and restraint is a whole other can of worms.
Think About Timing and Audience
You don't have to be funny all the time (or even on demand), so don't expect that of yourself. Don't let other people expect that of you. When you catch yourself trying to be funny, slow down.
Even if you're parroting, slow down when you're telling a joke. It's scary because you're probably thinking, "Don't mess up this punch line. Don't mess up this punch line. Don't mess up this punch line." Simply speak slower so you're not as likely to stutter. Try speaking at 60-70 per cent of your usual rate. Pause in between sentences. Gauge feedback on your attempts.
As writer Carol Burnett says, "Comedy is tragedy plus time." When you're considering your audience, make sure that enough time (but not too much) has passed and that no one is saddened or threatened by the tragedy. It helps if the tragedy only affected you. A study published in Social Psychological & Personality Science examines the "sweet spot" of timing:
Time creates a comedic sweet spot that occurs when the psychological distance from a tragedy is large enough to buffer people from threat (creating a benign violation) but not so large that the event becomes a purely benign, nonthreatening situation.
If you're about to tell a joke, there's no need to preamble or announce it. Just tell it. Be appropriate with subject matter. Even if you find something amusing, it doesn't help your cause -- to delight other people -- by offending a colleague or friend.
Once you say something to the world, it's out there. If it's about yourself, it can be perceived as self-deprecating and can be funny while offending as few people as possible. If you find something amusing, ask yourself -- will it offend someone? Is now an appropriate time to say it?
Know When to Let It Die, or Pull the Plug on Yourself
Few things are more cringeworthy than when someone tries to continue a bad story. Sometimes, it's not a fault with the story or joke. Maybe it's just not a good fit for the audience, or perhaps it's poor timing. Maybe you're not as comfortable telling it, so you can't deliver it properly. Either way, if you feel the joke floundering, just let it die. Better yet, just end it yourself.
Depending on the situation, you might be able to recover from it. Here's how comedian Mitch Hedberg once told a mediocre joke to his audience, and turned it around:
I didn't go to college, but if I did, I would have taken all my tests at a restaurant, 'cause the customer is always right. (reacting to meager applause) All right, all right. That joke's better than you acted. Perhaps it's not. Maybe it's dumb. It could be. I hear you, man. I'm not a fuckin', genius, for Christ's sake, you know? I'm just tryin' to tell some jokes. Shit, who the fuck are you? That track is number 14. It's called "Attitude."
You don't need to seize every single opportunity to be funny. If you're in the middle of a bad joke, just end it. "You know what, now that I'm telling it, it's not as funny as it sounded in my head" can be a bit of an awkward end and bruise your ego a little bit, but it saves everyone time and patience. In the long run, they will respect your taste. Let the joke slip away into the abyss.