How to Woo Women: or, a Post I Never Thought I'd Write but I'm Up Late and Distracted

Well, I have decided to bust out of this slow as glass life of mine and ask someone out. I don't want a girlfriend but I would like to do a little dating.

I spent a couple of hours lying awake tonight and while I was staring at the ceiling in between tosses and turns, I began to toy with the idea and try to pick apart, as I do, my motives. I came to the conclusion that the main idea is that I want to date, I see a prospect and it is therefore reasonable to take my chance.

Here is my guide to wooing women*: Enjoy and good luck!

Step One: Scout discreetly for gossip as to her likely disposition. This is tricky. Asking her best friend is usually not a good idea because her best friend is approximately 64 times more likely to let the cat out of the bag than any other acquaintance. If you're after a girl in your Greek class (and I usually am - I highly recommend it) then female classmates are a good bet.

Step Two: If the gossip seems propitious, invite her to join in a group outing. During the outing, be sure to sit next to her and find the occasional aside to whisper to her. It's best if you can make her laugh but it's enough if you can find a time to exchange glances. If all goes well, proceed to Step Three**.
If her response seems lacking, consider leaving well enough alone, or repeat Step Two in case she was just nervous.
If it all falls flat, it's probably best just to let go and return to Step One with a new woman in mind. Alternatively, throw caution to the wind and skip ahead to Step Five or Six.

Step Three: Step Two having gone well, invite her to have a drink or coffee with you. This gives you a chance to demonstrate your interest subtly by opening doors, fetching the drinks or even treating her, if finances allow. If she seems a little flustered by the attention, this is a good sign. If she doesn't but begins to flirt a little, this is a good sign. If she seems sullen or confused, then use your discretion about proceeding to Step Four; it may be time to jump ship.
Alternatively, proceed directly to Step Five or Six.

Step Four: Invite her on another group outing. Pay the same extra attention to her quietly in front of the group. If she takes it as her due, this is a good sign. If she beats you to the punch, this is an even better sign. If she seems flustered, this is not a bad sign. If she seems eager for you not to do what you're doing, return to Step One - it's a lost cause.

Step Five: Plan the date. I prefer arts events, especially opera. Picking a date that will not require you to make conversation throughout is a very good idea. Time spent together not in conversation allows each of you to try out being around each other without too much pressure. I do not recommend a dinner date for the first date unless you are a loquacious extrovert. The main thing is to take her somewhere where you feel at ease and where you think you can make her feel at ease.
The main event of the date should always be followed by a drink or wandering walk home or similar. Give yourself a chance to take hold of her hand before the night is over.
(Nota bene: Planning to do anything more than hand holding is likely to backfire.)

Step Six: Consult the bird omens carefully and then ask her to a coffee or drink with you. Show the same attentions as in Step Two or, if applicable, receive her attentions gracefully. About 40 minutes into the conversation, it's time to broach the subject. Depending on her experience with dating women, this can range from a simple and direct "May I ask you out sometime?" to a still direct but less aggressive inquiry along the lines of "How do you feel about women?" or if it seems very touch and go, a low key "I've really enjoyed spending time with you this last couple of weeks." Whichever option you choose, be sure to lead in gracefully***. Compliments are a great idea.
If you get a yes, or she beats you to the punch, proceed to Step Seven. If you get a no, bow out as smoothly as you are able and return to Step One with a new woman in mind.
However you plan to get through Step Six, be sure to arrive with an actual date, time, event and transportation plan in mind.

Step Seven: Spend some time making sure that you have decent underwear and some of whatever she likes to drink in your freshly cleaned home with new sheets on the bed. You'll feel better during the date knowing that your home is tidy. (I do, anyway, but it now occurs to me that this might be little odd. I wonder.) It is at least as important to insure that none of the clothes you plan to wear have holes in them, unless of course, having holes in your clothes is what you do. If you need a haircut, get one now.

Step Eight: The date itself. Relax and enjoy. You have successfully wooed a woman, or, possibly, gotten yourself wooed. Either way, take a moment to rest on your laurels, but only a moment, mind. It's time to repeat Step Six, with appropriate variation until you call it quits or move in together or get married.


*If you have your eye on a butch woman, you will need an entirely different approach focused on enticing her into asking you out. Instinct and sneaking in glances and casual physical contact works best for this.

** If you're involved in one of those wonderful and suffocating lesbian things where you're still more or less glued to your ex, now is the time to give her a warning finely balanced in directness and vagueness. It's only fair.

***Gracefully is good but if you're a nervous person (are not we all to a variable extent?) and the only way you can get the words out is to be abrupt, then just go for it, blurt it out. If she likes you, she'll think it's charming. If not, you're better off without her.

I'm starting Step One tomorrow. Wish me luck.