Don't Wear the Pants*
First of all, if your name is something boring and respectable, adopt some kooky nickname, like... Mookie. That will be her first whiff of your utter manliness. Once that's settled, do everything you can to make her the man in this situation. Go ahead and ask her out to dinner, but when she accepts, twist it around so that she was somehow the one to ask you out. The key here is mixed messages. Tell her you'll make the arrangements, but by that you mean you'll give her some options. When she expresses confidence in your ability to plan the date, ask what kind of food she likes -- but when she answers you, don't just select a restaurant like some kind of patriarchal dictator! Give her some choices anyway. Whatever you do, don't make a decision. What if something goes wrong? You want to make sure it's her fault. If the whole business of planning the date takes fewer than three days, you're doing it wrong. This is best achieved by conducting the entire conversation through texting. (Bonus points for using ellipses to end every... single... message...)
Shame Her Into It
The goal here is to show the woman what a problem she is, in order to present yourself as a solution. Just watch how Felix does it. (Pro tip: Pay attention to his exquisite use of filler.)
"Blah blah blah how old are you? Blah blah blah you're single right?" Now step it up a notch: "Blah blah blah I know it's hard, being a single woman in this society..." (Show how understanding you are by offering your sympathy -- nay, empathy -- for how pathetic she is. Trust me, she will be shocked.) "...blah blah especially getting older..." (Never mind that you are just as single, and older than she is, and not a woman at all. Having a vagina is practically a disability -- one that you are totally qualified to represent because blah blah.) "...blah blah social status..." (Remember, "marital status" is synonymous with "social status," so choose the latter for the sake of clarity.) At this point, if she's not falling for you -- she never will.
*Figuratively speaking, I mean. If you're chasing women without wearing pants, this lesson is too advanced for you.