For those who don’t know, the ” cocky and funny ” approach deals with being humorous and challenging at the verbal level. Some swear by this approach however, the challenge is that not everyone can be funny. Learning humor takes a great deal of work, and timing skill. Learning to be cocky or challenging is another specialized skill the involves innuendo, double entendre, and especially subtlety. I believe this last area is where you’re finding the challenge.

You see, younger women aren’t as intuitive as older women. This is simply a matter of experience. Most women in their 20’s soak this up because they are challenged by even the coarsest humor. As women get older, they expect much more subtle, evocative interchange. Think “stand-up philosopher” rather than “stand-up comedian”.

The fact is that the cocky/funny approach WILL work on older women, however you have to refine it dramatically. You have to be topical, timely and have great finesse in giving it. It is for this reason that I generally recommend against using this unless a guy is already a student of human behavior.


As I’ve mentioned before, I don’t generally recommend the ” cocky and funny ” approach as most guys really aren’t funny. Further learning how to do this takes some real work, and is difficult to target because you have to really size up the woman you’re dealing with.

That said, it isn’t impossible to learn. Here’s how it works:

First, being “cocky” is a matter of degree. If you’re too cocky, you look like a jerk. If you’re not cocky enough, you look insecure. It is a very fine line. That’s one of the reasons why so many guys try to add humor to their cockiness. It tends to “soften” it a bit, letting them take it slightly farther than they could otherwise. But believe me, humor isn’t an absolute necessity.

Further, once you start this, you have to keep it up. If you let your guard down, or she “slips by” you’re going to have a hell of a time regaining control. You’ve always got to keep in mind that women are better at this game than you are. Thus, don’t drop your guard.

So, here’s how this works: think about “busting her chops”; that is, challenging her and calling her on every detail. For example, you and she start talking, you attitude should be that you control the situation – not her. You can say things to her like, “Yeah, you’re cute, but I’m used to dating much younger women”, or “Gee, what an interesting color for a dress”. The point here is that you’re not complimenting her, you’re challenging her.

She may come back with something like, “Are you saying you like the color of my dress or not?” You’ll respond with, “Well, I’m not sure yet, let me look at it on you for awhile.” The point is to keep her guessing. She may ask you direct questions like, “What do you do for a living?” Your answer should be vague. Don’t say, “Oh, I’m a lab tech” or something equally boring. Say, “Oh, I work with chemicals, like the ones in your hair dye.” By the way, you want to do all of this with a straight face.

You can also ask her “directed” questions like, “So, what do you do for a living?” If she comes back with something that sounds high-falutin’ you can bust her again. Let’s say she says, “Oh, I’m a corporate attorney with a large law firm in the city.” You can shoot back, “Oh, that’s nice. And what do you want to do when you grow up?” The key here is to be absolutely serious. Don’t let on that you’re making a joke, or she’ll instantly sense weakness on your part and just think you’re being a jackass.

Likewise, if she comes back with something that is less impressive, don’t bust her – she may be sensitive about it! For example, if she says, well, I’m working my way through school as a waitress”, don’t bust her here. If you do, she’ll just be offended – not challenged.

This approach is somewhat complicated and takes time to perfect. I feel there are much easier ways to approach women, especially if you’re already funny anyway.

Dr. Dennis W. Neder the author of Being a Man in a Woman’s World. Got a love, relationship or man/woman question ? I answer all letters. You can write to me at [email protected] for answers.Back to Dennis’s Columns