Much has been made of “The Cougar” in the last few years- websites, TV shows, Demi & Ashton.. well, you get the idea. Looking back, it’s really not a new idea that a mature younger man would gravitate towards an older woman who doesn’t care what kind of car he drives, who he’s friends with, or if he’s picking up the tab at the end of the night.

You see, the advantage to an older woman is that there is no superficial bullshit to deal with. She wants you to do one thing and do it well- that’s all that is expected of you. If you’re a busy guy (and you should be- that Azimut isn’t going to pay for itself) you can immediately see that there is a pretty big ROI in the Cougar market.

Well, as they say, we'll always have Paris. And the pool table.

Well, as they say, we'll always have Paris. And the pool table.

But most of the articles I see on this subject seem to be written in theory (or worse yet, by women themselves) and spew crap like “Take her somewhere exciting and expensive” or “brush up on current events” so for our younger readers I figured I’d lay out some simple ground rules from a weathered old Captain who has long since hung up his sails:

  • This isn’t a relationship. You don’t pick her up at 7, wine and dine, and then cross your fingers that she wasn’t just using you because she’s broke and couldn’t afford a meal. The only question after initial contact has been established should be “my place, or yours?”
  • You are a ghost. No contact with kids, family, her ex-husband, or otherwise. If you stay the night you better be up and out of there before anyone else in the house starts their day. Conversely, never -ever- ring a doorbell or feel like you can waltz in and plop your feet on the sofa unannounced. Follow the protocol she gives you.
  • Don’t freak out about dating other women. It’s an unwritten cougar rule that they will not approach you if you’re out in public with a younger woman. But that’s the key- younger. If you’re out with another cougar, god help you. Along the same lines, you can feel free to consider the agreement over if you spot her with another younger man.
  • Forget it. By sleeping with her, you’ve given up all rights to date her super-hot 22 year-old daughter. Sorry, it’s one of the rules of the road (and pretty sleazy too boot).

One last thing- if you manage to stay within those very simple boundaries, keep her happy in the sack while maintaining her public persona you’re probably going to find yourself on the mythical “referral” program for a long time to come. Unlike younger women, they have no problem sharing a good experience with their friends (and in more ways than one).

I just sort of fell into it.

Deuce, you the best he-bitch in my man stable. If I had two more manginas like you, I'd be a millionaire.

Happy sailing!

Black Swan