The Date Itself
Women realize that this is the twenty-first century and we (the general population, at any rate) realize that we are lightyears beyond women's lib. We won the vote, we broke that glass ceiling, we can do it.
Still it is, on occasion, nice to be taken to dinner. I mean "little woman doesn't pay for anything, no no, the bill's on me, and would you like dessert" dinner. We understand that equality between the sexes was fought for and subsequently won. We appreciate the Suffragettes very much here in the present. However, it is an extreme aphrodisiac to be pampered like a princess. Particularly on the first date. Make a good impression.
That's right, Gents. At least offer to pay for dinner/her movie ticket/drinks. She will let you know if she feels the need to pay her share for the evening. Let her decide whether or not the two of you are going Dutch.
Do not order anything for her. We are adults here (hopefully you are not taking a minor out) and women know what they want. At least insofar as to what they would like to imbibe. The only time you should speak to the waitstaff/bartender on your date's behalf is if she has left the table or has expressed consent for you to relay her drinking or dining choices.
No McDonald's. No Burger King, no Taco Bell. This is not acceptable unless the two of you are already in an at least semi-steady relationship. Or if you're in somewhat of a rush to catch the nine o'clock show.
On that note, let her pick the movie. I don't care if you don't like Ryan Reynolds or romcoms. If she wants to see it, apparently she does like these things. Or she's testing her boundaries with you. Suck it up, buttercup. You want this date to end well, do you not? Besides, you might just (gasp!) find yourself liking the flick. If not, then maybe you can choose the next time.
Do not compare her to your mother.
Do not compare her to past dates or previous girlfriends. Ever. This makes for a seriously awkward situation.
Do not prattle on about yourself for hours on end. Especially if she seems to be feigning polite interest. If you sense that she is mere seconds from rolling her eyes and pretending that she has a phone call to end your monologue, then she probably is.
Don't ask if you're boring her. She will probably, for the sake of civility, say something along the lines of "Oh, no! Do go on!" and give you a hopeful smile. Hopeful because she really wants the subject to change but may be too nice to say so.
Poor thing. Not every girl can be brutally honest. Particularly when she's trying to make a good impression.
Talk about her. And if you ask questions, then listen! There is (nearly) nothing more aggravating than having to repeat yourself several times in one sitting. Really, it indicates that he opposite party involved in the exchange is not paying attention and thus must find you dreadfully dull. If you don't want to know, then don't ask.
Because she will probably tell you.