How to Ask a Lady Out

Pretty Lady had to chastise the Pundit, once upon a time, not so long ago, whilst the Pundit was still single and actively chasing females on Nerve.com. He complained to her, "I get chatting with a woman, and everything seems to be going fine until I give her my phone number. Then things just trail off."

Hello? Pretty Lady was momentarily speechless.

The Pundit, she thought, had little excuse for this. Pretty Lady met the Pundit once upon a time on Nerve.com, in fact, and he was one of the very few gentlemen she accepted into her inner circle. The Pundit is a Real Man, a mature and intelligent soul, and he knows how to treat a lady. The fact that Pretty Lady did not marry him herself in no way reflects upon his qualities as a mate; they simply didn't suit. Like a true gentleman, once his amorous overtures were regretfully declined, he gracefully continued to be her friend and champion, and she in turn was one of the first to embrace his lovely bride. This is how civilized people behave.

This is why she was so shocked. "Once you give them your phone number?" she inquired.

"Yes, I don't want to ask for theirs, lest they think I'm stalking them," the Pundit replied. "That way they can decide whether to call me or not."

Gentlemen, I respect your delicacy, but listen to me: never do that. Please.

The poor Pundit was falling into a trap made of false liberalism. His motives were pure; unfortunately, too many of the motives of those who went before him were not. Thus I had to explain to him what these women already knew; that a man who gives a woman his phone number is generally either 1) insecure, submissive, passive-aggressive and pathetic; or 2) an arrogant user who sows phone numbers as seeds for booty calls. In effect, such a man is saying, "I don't want to get entangled, but if you want sex with no strings, give a buzz and I'll oblige you. If I'm free."

So what's an honest gentleman to do, in this confusing day and age?

The method is very simple. When you meet an attractive lady, either online or in person, get a piece of contact information. This could be a phone number, an email address, a Blackberry text-messaging thingamajiggy, whatever. In our society this cannot anymore be construed as 'stalking'; gracious, anyone who knows Pretty Lady can Google up her entire life story in six seconds. Relax already.

Then you wait a decent period of time. The minimum should be two days, preferably three; the maximum a week and a half. More time and the lady may well have forgotten who you are; less and she will assume you have no life. The only exception to this rule is if you met Pretty Lady on New Years' Eve and are leaving for Ecuador for three months on January 2, and want to be sure she remembers you upon your return. (Craig, darling, the sushi was wonderful.)

When you contact the lady, via phone or email, a few simple rules must be observed. Keep it short, casual and friendly; ask her to do something which will engage her interest but not impart an undue amount of pressure. Invite her for coffee, or biking in the park, or to hear a garage band made up of your own acquaintances. This first meeting is for the purposes of discovering whether the two of you have enough in common to make it through a dinner date. Pretty Lady can attest to the fact that there is nothing more draining than sitting through a two-hour meal with an individual who has not cracked a book since 1987.

On this first short date, do: pay for the coffee. Listen. Ask reasonably intelligent questions. Show up clean, sober and dressed. Depart gracefully after an hour, two at most, twenty minutes if the lady is a psychotic nightmare. Kiss her on the cheek, in a non-invasive way.

Do not: whine. Insist on going dutch. Show up in yesterday's sweat-stained farming clothes. Talk endlessly about yourself without letting her get a word in edgewise. Ignore her cross-legged, tight-lipped body language and offer to jump into her lap. Pretend to be an insane person because you think it is funny. Slobber on her face. (These things have all actually happened to Pretty Lady.)

You cannot possibly get into trouble if you follow these rules. If there is instantly, obviously no chemistry, you have not wasted a lot of time and the price of a meal; if there is, you surge confidently ahead and ask her out for the works. If she's a cool girl and you do not suit, you have made a friend--and girls have friends, too. Since you followed the above rules, you will surely come recommended. At the price of a cup of coffee, this is an incredible bargain.

Coming up next: How to Ask a Gentleman Out (or not).