When an attractive woman has asked me a question, I have always assumed genuine interest.
This assumption is as far from the truth as possible-- the last thing she wants to do is listen to you ramble about God knows what. Honestly, who cares what you just did 3 hours ago? Chances are, you're not that interesting, and telling her exactly why can not possibly contribute to your best interests.
The solution? Say as little as possible. Be stoic. Give nothing away that could turn her away. The results?
1.) maintain an air of mystery
2.) let her do what she loves to do: talk about herself.
If she asks you how you're doing, a simple "fine" will suffice. Insert witty comment if you're confident you can pull it off. Next, simply do like girls do: ask her the question back and keep asking follow-ups until her verbal train leaves the station. At that point, just relax and phase in and out of consciousness (or actually pay attention: your choice). Congratulations, you're a great listener.
The only issue here is that you may get tied into a conversation about something you care nothing about. Shoes, for example-- avoid shoes at all costs. There is a fine line between good listener and the friend zone, from which you have little hope of escaping (addressed in a future post). Once you have incited a dialogue about pumps, you've certainly taken a wrong turn. Learn as much as you can about her past, her good friends, and her family, but avoid pointless, shallow banter.
The goal is to figure out what she is thinking and how she regards the world around her, while maintaing a wall-like presence. The questions should always be, "what does this tell me about her?", and if any red flags come up, "should I run for the hills?"
If you find yourself cornered and have to talk about yourself, keep it simple, interesting, and keep her involved in your story. In fact, take any opportunity you have to stop talking and let her tell you of a similar experience she may have had. Unless you lead a life of endless philantropy or have recently toured the continent with your alternative rock band, she will not only lose interest, but you will also miss out on a chance to learn what she is thinking.
When she is doing the talking, you are giving nothing away about yourself and can only stand to learn what is going through her mind. But start talking, and she has this luxury.
Unless you have told her exactly what you have been doing all day, she may, in fact, assume that you have been dishing out soup to the homeless for four or five hours. You might be a nice guy, but you might also have four motorcycles and enjoy riding off into the desert at 2 in the morning when you're feeling sleepless.
Boring or not, just keep your mouth shut and you don't have to be.