CCC,
Throughout my life my main advantage with women has by far been my sense of humor, and I have been told by many people that I am one of the funniest people they have ever met. However, a really good sense of humor is very hard to learn naturally if you aren't already inclined to be amusing.
I have never had the problem of not being funny, but I can offer you some advice that I have noticed from observing other's reactions to me and other funny people as well as other's reactions to people who aren't viewed as funny.
To me, and I personally believe universally, humor is all about timing and delivery. Take this example;
One time I was walking with one of my friends with zero sense of humor and a girl we both knew to lunch. I said something that could be interpreted in both a platonic and a sexual way to the girl about my roommate and my friend tried to point this out in a humorous way, but failed because he delivered his comment a couple seconds too late and murmured it under his breath quickly rather than openly stating it. He also make the mistake of laughing a little to loudly at himself. All three of these things killed the joke that would have been funny if he had jumped on the opportunity immediately, spoken up, and simply smirked and let the "audience" he was aiming the joke at laugh instead.
I actually tested this out one time on my same friend, when someone said something that was begging for a witty retort, and the kid muttered one under his breath, I said the exact thing he had said that no one had heard over him and everyone bugged the fuck out. Basically the keys to general funniness are;
1. Time it right,
2. Speak up,
and,
3. Don't laugh harder than people laugh at your joke/comment.
However, that is just generally being funny. Being witty with a girl one on one, in my opinion, is about pointing out small, amusing things at appropriate places in the conversation and poking fun at them or putting a humorous spin on them with a bit of sarcasm.
Your goal should be to have a sort of tongue-in-cheek view on everything except what she is deeply passionate about and what you are. I find a lot of deep diving success with framing myself as a devil my care type of dude who isn't serious about anything and is able to find humor in everything, until I suddenly show a hint of seriousness at something I am truly passionate about and use that spark of passion to pique her interest in me, eventually drawing out her inner hopes and dreams so I can move the conversation to a more serious place that she never expected it to get to.
The trick is maintaining the sexual frame while coming off as a humorous, carefree individual; the key is to rather than come off as a clown, come off as slightly, edgily jaded with dryer humor, while still keeping the mood light (you don't want to depress your date, just let her know that there is something a little deeper to you that shapes and defines your "merrily cynical" worldview.
Hope this helps,
Jay
