Post: #1

like conversation starters and
keep making light jokes for the whole part.

Post: #2

Toastmasters.

Post: #3

Are you funny when you're around your boys? If so, do that. It's the fear and pressure you put on yourself to be impressive that stifles humor.

Post: #4

Why do you feel the need that you need to be funny in order to attract women?

Post: #5

Ask her what you call a bear without teeth. When she says I don't know or something of that sort, tell her it's called a gummy bear.

I guarantee the panties will be off post-haste.

Post: #6

King of Monkeys has it.
It's the same care free attitude as with your guys, but with chicks being mostly silly works because they're so infantile.

Post: #7

Witty + silly + lots of making up stories.

For example, say you are sitting in the park, and you see some couple on a bench across the way (but out of earshot).

You can make up a ridiculous story about them based on their body language.

Sometimes I'll jokingly just start running the dialogue of "lame guy voice" and then "whiney girl voice", making up what they are saying to each other. The key is timing and delivery, knowing exactly when to switch voices. Then as soon as something coincidental happens, like the guy throws his arms up in the air, I'm escalating in "his voice" something matching that. It's fun and looks like I already knew exactly who / what they are. Maybe they are having a fight because he wore those stupid sandals+socks out again (or whatever you pick on).

I might stay in that zone for all of one or two minutes, then change the subject, not laughing.

But that's something I'd do with my boys also.

With a girl it's emphasizing the "you and me vs. the world" bubble, thinking on my feet, creating entertainment.

It's not about "being funny", it's about being fun to hang out with in whatever way you bring the party / vibes / entertainment out of thin air.

--

Also another fun gambit is deadpanning ridiculous stuff to the people you encounter, with the girl.

For example, say you two walk into the cafe and a hostess greets you. You can say something ridiculous with a straight voice and face to the hostess like "Hey, do you have any tables that are great for eavesdropping? We aren't interesting enough on our own..." And then smile to show you're just fucking around.

Imagine that's an hour after my first park bench example -- so now you're recalling the previous fun bench antics, and dragging this new hostess into it. The hostess won't fully "get" it, but your girl will and now it's hilarious that you brought this hostess into an inside joke somehow.

I'm spitballing here, but it's not about being funny, it's about witty entertaining fucking around. This is congruent with me and how I joke around anyway.

If you're shy and don't have a certain kind of presence, you might have a totally different way of creating fun like this.