I understand where the question is coming from. The fact that women are generally not as funny as men has been beaten to death. It's absolutely true in my experience. More guys are generally trying to look for ways to be funny, and the ceiling for humor has historically been way higher for men than women. There's just little incentive for a pretty woman to develop her funny muscle.
What's funny is normally unexpected. You gotta think differently. Girls generally don't push boundaries enough to be considered hilarious. They can get me to chuckle and laugh unintentionally, sure, but to truly surprise me and catch me off guard,
intentionally?
Very rare.
I've only met one two girls who were legitimately funny, but was only in a relationship with one. I'll oblige the OP and describe what she said and did. Two times stood out.
1. This was in the early stages of a long-term relationship. Area code score 7.5-1-7.5. Very proper, always nicely dressed and well-kept. Also very smart, A-type. Juicy titties and ass. Decent trophy, if I may say so myself.
We were in my new car, one of the first few rides I had given her, although we'd been together for a few months. We were getting back from a dancing outing, but it was still daylight. Basically, she was in a good mood, endorphins rushing from the dancing, car, and the dicking she was about to get as soon as we got to my place.
I proceed to put on some music from my iPod. An uptempo Portuguese song comes up. She starts singing gibberish in whatever Portuguese sounds like to a person who only knows English, which always got a chuckle from me. Kind of like the way a little girl might sing to songs on the radio.
So she's 'singing' incoherently as I'm driving. She then takes her perky C-cup tits out, in broad daylight, and cups them and shakes them while near screaming Portuguese gibberish. I almost drove onto oncoming traffic from simultaneously laughing and ogling that prime juicy sweater meat.
Humor recognized.
2. We were at a party with some of her coworkers. The topic somehow steered to Louis CK and his no-holds-barred stand-up. I told them I thought he went too far with one joke, and proceeded to tell them about the bit he does where he walks into a room to find his
four year old daughter on the floor maniacally gaping her vagina (30 second clip).
The whole group chuckled, which was unexpected, so I guess the joke was funnier than I thought.
Anyway, one night a few weeks after the party, we had just got done banging. She gets up to go get some water on a table across the bed. I watch her and take in her juicy titties and ass in the dim lighting. I say, basking in the afterglow of a good nut,
"Goddamn you look good."
She looks at me. Doesn't even crack a smile. She then hunches over, sticks her tongue out, and eyes bulging starts screaming 'Aaaahhhh!!!!' and, you guessed it, gaping her pussy. Never had she been more beautiful.
Humor
really recognized.
_______
Girls can be funny, but it's rare. This girl grew up in a big city where her cute looks were... pedestrian. She also grew up with a
hilarious and really quirky father and older brother. I still laugh with and at girls all the time, I enjoy their flighty company. But let's face reality... I have tried to sit through female stand-up, the likes of Sarah Silverman, Wanda Sykes, Chelsea Peretti, Lisa fucking Lampanelli... and I always regret my decision. They're simply not on par with the heavyweights.
My favorite female stand-up is actually Maria Bamford:
WB multiple times. She does a lot of voices, so the role play would be great.
Otherwise, Patrice said it best.
Women rarely get men to emotionally invest in them because of their humor. Just leave that to us ugly motherfuckers.