I think it depends on the kind of sense of humor you have and the overall frame you are projecting. If you're more the dorky/self deprecating type then certainly it won't work, although she would laugh and enjoy but will also friendzone you in the process. However, if you're being dominant/cocky/alpha and using humor along with it, then that combination can certainly be deadly. Humor certainly is a way to display how you are in control of the things around you and how it's all too easy for you. Almost all the successul business/high ranking professional types cats I've met had one thing in common - a great sense of humor and an ability to crack jokes frequently.
Game is a necessary evil