How Not To Impress Your Date

Gentlemen, it is time that Pretty Lady administered a bit of Brutal Reality to your fond imaginations. The word on the street is that you are getting cocky.

Indeed, it has long seemed to Pretty Lady that as long as there are Rules, would-be clever boys will try to find a way around them. Worse, they address these Rules from a lawyer-like persepective, adhering to the letter but not the spirit of the law. Their goal is always to obtain double helpings of cake without having to pay for it. Sadly, boys, the ladies are seeing through you.

Thus it falls to Pretty Lady to inform you that when, on a date, you attempt to score double points by stating, "It is not my habit to pick up checks, but I will do so for you, just this once," you are not scoring any points at all. Obviously, in your mind, you believe that you are getting credit for both Enlightened Egalitarianism ('it is not my habit...') and Situational Generosity ('but I'll do so for you.')

Instead, you are coming off as a stingy, fatuous ass.

For what lady wishes to pursue further acquaintance with a gentleman whose notion of extravagant generosity is spotting her a couple of drinks, on spec? Visions immediately flood through her imagination--of working extra shifts at the co-op to pay for her half of the engagement ring, of phoning the office from the maternity ward to make certain her half of the rent is covered, labor pains or no.

She then thinks, "If this is as good as it gets, I am so out of here." Sometimes she thinks this even before the actual date.

So gentlemen: shut your traps, and pick up the check without calling attention to your action. The lady will notice. She's not an idiot.