Wit comes from a sense of humor and knowledge in my opinion. The more you know the more you can interject some funny material into a conversation.

Say things without thinking. Eventually someone might think it is funny.

Ask yourself the question, what would bob_ do?

Mostly by knowing stuff. You need to be able to make connections to all kinds of things. Or rather, your mind has to do it automatically. Be playful. Go with the first thought and don’t stop to think. Or don’t stop to think and go with the first thought. Something like that.

It helps to be absent-minded, and to have a hard time paying attention. Then you mishear things and your responses are a little bit off. After a while you can say your are being witty and they just don’t get. They should pay attention. And you huff away. Eventually they’ll laugh instead of watching you huff.

Hang around with me. Just kidding!

Very interesting question. How does one become witty if one is not naturally?
Not sure about this but try to study again the different figures of speech ( metaphor, simile, hyperbole etc. ) I have a feeling every witty remark we hear comes in the form of one of them.

Next is you have to sit still, clear your mind so you can focus on using your powers of observation. Your mom’s wit may come naturally but for sure she notices things and she may or may not be aware she’s doing it because it’s in her subconscious. Her wit is spontaneous. You on the other hand wants to learn so that’s a challenge.

Lastly, read books, lots of them, especially about humor. Pick a classic, get a contemporary one as well. Also update yourself with the day to day global goings on in science, societies, politics, economy and entertainment world. That will expand your knowledge and perception making your mind a fertile ground for witty saplings sprouting into mighty gigantic oaks! Goodluck.

Pepper your speech up with a bunch of “fucks” and drink so much that you simply don’t care anymore whether someone thinks you are funny or not.

be prepared to cry yourself to sleep a lot

Make humorous comments, which relate somehow to something y’all were laughing about a minute, an hour, a day, a week, etc. ago

Make jokes which connect what someone just said to current events. Or well-known literature, or pop culture, or a in-joke.

It’s all about quickly and eloquently making and voicing the connections that others didn’t clock… watch some panel shows… British panel shows.

Hang around with @janbb . Not kidding.

Seriously. though, I think my wit is an almost unconscious part of my personality. It certainly comes out of a familiarity with literature and language, with history, with current events but I make verbal connections and “hear” funny things almost without thinking about them. It was also a defense mechanism and a way to get attention in a very intellectual family and with a sarcastic British husband. If you aren’t wired that way, it could be hard to develop. You could try making a note of what amuses you and see if you can make the same kinds of connections. However, if it isn’t a natural part of you, it can fall flat and you may want to just focus on the parts of your personality that are really you.

No, really, hang around with @janbb. =)

Let’s all hang around @janbb ! Party in the library!

WOOT! WOOT! Sangria in the stacks; cheese and crackers on the card catalogue: dumplings in the databases! PAAARTAY!

@janbb . . . the jewish part doesn’t hurt either. isn’t it a societal defense mechanism?

@Blondesjon I once told seazen my sense of humor was schmaltz on wry so you are probably right!

Read Oscar Wilde.

watch a lot of Bob Hope movies.
You’re not learning his lines, you are learning the style, timing, and out of the box humor.
He is the King.

@wundayatta gets a good theme going with absent-mindedness, I was going to say relax. @janbb says it’s unconscious. @mazingerz88 says sit still and work on the powers of observation. Takes all that. The monkeys in your head have to feel free and safe to jump around and throw things and grab things to make connections and you have the witness aspect of your attention available to watch them. And you simply cannot be afraid to be silly !

It helps to have a good sense of humour but more than that, be confident and don’t worry about making a fool of yourself. As @mowens said, eventually someone will find you funny. If you lack confidence, you will always be second-guessing yourself. Just let your mind free and if something amuses you, share it.

I have thrown a few well timed witty comebacks, evidenced to me by the acclaim of others.

Timing is important which comes from familiarity with information stored in my brain which comes from review after the fact and discussion with others. Habits that build this aspect are: being well read in books, well ‘watched’ in movies of all sorts, and being knowledgeable about whichever subject the audience understands.

Sense of humor is a part which is developed by understanding the audience in questions and getting a SENSE for what they will find humorous.

Intense life drama seems to play a role in wittiness as well, while allowing one to cathartically express leftover emotions. For instance: “ex-wife or ex-husband comments” “That’s what he/she said” comments.

Having all these factors on speed dial kind of naturally happens as one comes to terms with them, or is discussing/thinking about them in the process of coming to terms with them.

I never think.