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dont care whether or not anyone will laugh, then say exactly what you are thinking. .also dont laugh at any of youre own jokes. you dont get to laugh at anything you say until someone eltes does. it dosent matter how funny it is. ...thats my rule..

I completely disagree. I always laugh at what I say, that said I have a ridiculous laugh so I get away with a lot more then most people. It is actually contagious according to everyone around me.
The art of being funny is simply an unexpected ending. Think about it any good story you laugh at has an unexpected ending. So when you comment about something it should be unexpected.
I like your earrings but I am always distracted by bright lights and shining objects.
Man what are you the creepy girl here?
Ooooh awkward moment, gotta love the silence.
Being overly animated is also a good way to do things, of course you have to find out works with your specific persona. I am a goofy guy and so I can get away with certain things.
Borrow from movies, TV, stand ups, etc. There are all sorts of great quotes that you can use plus if she knows the movie or show you can already relate, and if not you can convince her you guys need to watch it together.
Stating the truth with a twisted blown up style. Question statements with a over exaggerated truthful outside take on their statement. Hard to explain. It is very situational. Over analyze their actions in a goofy way.
Oh so your saying you'd rather leave your mom at home than take her to dinner with your friends, she gave birth to you(obviously you must be very playful).
So what your really trying to say.... restate in a unexpected way.
Go buy a book, there are some that teach you how to be funny.