How to Ask a Gentleman Out

So, why would you want to?

Pretty Lady believes, truly, in the interconnectedness of all things. If any lady is considering asking a gentleman out, and feels a strong compulsion to do so, then go ahead, by all means. Your gesture will undoubtedly perpetrate reactions far beyond your ken. You may very well give the gentleman the necessary courage and self-confidence to pursue the woman of his dreams.

This woman will not, of course, be you. So long as you understand that.

Really, girls, if a man has met you, and spoken with you--been subject to the indefatigable brilliance of your presence, in other words--and has not yet had the wit to ask you of his own accord, what could be the reason for this? Pretty Lady can think of several.

1) He is married or otherwise attached.
2) He is perverted or gay.
3) He is the type of arrogant twerp who waits for women to come to him, then uses their initiative as an excuse to avoid any emotional, practical and financial responsibilities which might arise from the liason.
4) He is (unaccountably) Not Interested.
5) He is shy.

Can anyone out there think of other options? I will be happy to entertain them; these are the major ones which occur to me at the moment.

So then, presuming we have most of our bases covered--in which of these circumstances would a lady taking the initiative be a desirable thing? Obviously, asking a man out in cases 1-4 will only lead to extended misery, humiliation and heartbreak. Under all of these circumstances, the gentleman is to be greatly commended for restraining himself. Why would any sane lady want to force the issue?

But then, there is always option 5, which is not to be ignored.

Pretty Lady is not precisely an expert on bashfulness in men, but she DOES have a brother. She rarely discusses her brother in public, out of deep respect for his privacy. In this case, however, and with all suitable cloakings in anonymity and altering of salient details, her brother may serve as Exhibit A--the Bashful but Highly Desirable Man.

Well, of course he's desirable, he's Pretty Lady's brother, with all the genetic superiority of looks, intelligence and character which this implies. Pretty Lady could go on for days about the excellence of her brother, but his characteristics are already too well-known in private circles to require comment. In fact, her brother requires more protection than advertisement--since the age of thirteen he has been plagued by the more aggressive and clueless brand of female, throwing herself at his head. In his quiet discrimination he has kindly and politely parried these overtures, only occasionally with discreet telephone screenings by watchful female relatives.

Unfortunately for the women, however, Pretty Lady's brother is shy. He is also a bit of a workaholic; what with his undemanding Buddha nature and 80-hour workweeks, he may very well remain single for the next twenty years or so. This would be a tragedy for the advancement of the species. That is why Pretty Lady is breaking silence now; in the interests solely of the redemption of mankind, she will offer a bit of advice on how to ask her brother out.

The correct phrase is, "Yo! Dude. Why don't you take a break already, and come mountain-biking with me this weekend."

Note the salient characteristics of this phrase; its seeming casualness, confidence, lack of emotional pressure, and activity-oriented content. One can imagine the type of lady who could effectively deliver it--one who is comfortable with herself, one who knows my brother well, one who can take yes or no for an answer without any significant adjustment of ego-identity.

Should this lady be so fortunate as to receive an answer in the affirmative, she must continue to comport herself along these sportsmanlike lines. Her behavior must be calculated to help my brother feel at ease in her company. Warm, confident smiles, casual jokes, wide-ranging interest in both sporty and intellectual pursuits, a palpable lack of emotional pressure or fractious tantrums are all a must. Also a considerable amount of patience, and detachment from outcome. In fact, the lady must outmatch my brother's Buddha nature, in order to have a chance of success with him.

Pretty Lady is exhausted, just thinking about it.