Tag Archives: asking a woman out

you want tips? okay then: tips on the lost art of impressing a woman


The last post was a story. You wanted tips? Okay, then. Tips you get. I’m happy to oblige as we are living in an age of an ongoing courtesy crisis. These are basic and simple concepts, yet seem so beyond the grasp of many moderns. Because the situation is so bleak, it’s not that hard to impress a woman these days. Some basic guidelines:

♦ If you are interested in a woman, ask her out somewhere specific. As you are inviting her to be your guest, you pay. This is not sexist or backward. In fact, it is gender neutral. When asking someone to be your guest, man or woman, etiquette dictates that you pay. Ask her somewhere specific, and somewhere you enjoy. Dinner, theater, a concert, coffee, whatever—an activity that you enjoy and would like your chosen company to enjoy. If she does not, you will learn something valuable. Do not ask her if she wants to hang out. She is not your buddy and shouldn’t be treated as such.

♦ If she says no but seemed regretful and open to future plans, give it a week and ask her to do something else. A third time is pushing it. A forth time is out of the question. Respect no. She doesn’t have to give a you a reason. If she states that she’s taken, or declines for any other reason, no need for embarrassment or weirdness. Smile gently, say, “What a pity,” and make a graceful exit. She’ll wonder what she was missing.

♦ When asking a woman out, call her. Maybe email her. Do not text her. Do not text a woman, in fact, until you are married to her.

♦ When with a woman, do not, under any circumstance, engage in cell phone performance art. Do not touch your cell phone/iphone/gadget for any reason. Most especially, do not engage in conversation with someone else while she has to look away and pretend not to be embarrassed by your rudeness. Having a theatrical conversation with someone else to prove your popularity, worth, or importance (cell phone performance art) proves the opposite to any woman of substance. You will lose her.

♦ Be kind. Call when you say you will call. Do not be too eager, but do not be aloof. If you don’t want a woman who plays games, don’t play games yourself.

♦ Do not dump your psychological problems on a woman as a matter of introduction, and do not encourage her to dump on you. A bit of mystery goes a long way in romance. (Thank you, Judith Martin.)

♦ Mystery along the lines of unmentioned wives, children, allegedly monogamous relationships and the ilk (i.e. lies) squelch romance and are unacceptable.

♦ Do not flirt with or check out other women (or men) while you are with her.

♦ Do not speak unkindly to or about others. She will wonder not if, but when, she is next.

♦ Do not behave as if something is owed you on the third date, or at any other time. Where this third date idea came from is beyond my realm of comprehension. Behave as if you’ve never heard of it yourself. If things are meant to progress, let them progress naturally between adults, and not on some bizarre sex-in-the-city timeline.

Well, that’s it from the top of my head. Rereading the list, it applies to all genders and orientations. Tips for the courteous pursuer, if you like.

Comments/discussion/anything I’ve left out is more than welcome.