Dating Older Women

Dating an older woman is a beautiful encounter in which wisdom and exuberance trade their best portions in a shabby Motel 6.

Just The Facts

  1. Some people find the term "cougar" offensive and would prefer the original nomenclature: "cradle-robbing harlot."
  2. The most famous movie about dating older women is "The Graduate." Its entire soundtrack sounds like a tea commercial.

The Gist

Cougars have become quite popular since the film American Pie minted the acronym "M.I.L.F." (Matronly Individual Looking Fetching). While young men have always sought no-strings sex with ladies who can pay for their own meal, older women only recently took advantage, or at least stopped doing it covertly.

Mummy issues
Although cougars still tend to lie about their age.

Discrimination wasn't holding older women back; most 21-year-old guys would have sex with a bandsaw if it was on the pill. No, it was only this decade that everyone realized how boring The Graduate is, liberating our minds of its message that the only way older women can be sexy is as villains.

Here's to you, Mrs. Robinson
Make no mistake; evil is sexy.

After that dam broke, social disapproval could no longer protect our young men from sexy senior seductresses. Anyone who's witnessed Spring Break knows when women decide to cut loose, they behave the way men only do in a particularly large prison riot. If Andy Dick daubed PCP off Michael Vick's nightstand with his flapping knife wound, things still wouldn't get as raucous as an eight-woman bachelorette party at P.J. McSwagger's, route 10, Wilmington, DE. Those dames treat wait staff the way a Viking Berserker treats skulls.

Those are real Norse swears
You won't believe your eyes... are now jelly in the back of your head!

So at some point, sucking the life out of the young was yanked from the list of activities society frowns on women for doing while congratulating middle-aged men in Camaros.

Don't expect a relationship with your cougar. Some folks may hit it off, start a family, and be cursed by the Lord for their hubris with birth-defected children, but most understand the beauty is it can't last. To put it another way -- if you thought your ex-girlfriend's wedding was awkward, imagine what it's like if you've performed a three-knuckle merengue in the bride's Sunday school teacher.

Caring for your cougar

A Word of Caution

They're goddamn crazy.

On a scale of one to Lunacy, most cougars are "Bicycle Made of Babies."

We're not slagging them. Dates with older women can be really fun. We're just saying don't let them get your home address. If you can't protect yourself, you'd get safer kicks doing surgery at home to save money. The only thing comparable to a cougar for insanity, health-risk and awesometicity is the White Castle chicken ring.

I love you, Chicken Rings

Where to Meet Older Women

  • The comments section at the end of this article usually has some helpful spam.
  • At work - are you a pool boy or pizza delivery guy? Good news! As long as you can't break a $50, you're getting paid in SexBux! Just remember it's good form to shout "NNNOOOO!" when her cuckolded husband walks in on you two and shoots himself. The lunge to stop him is just for show, though.
  • Divorce court - Preying on the emotionally vulnerable can actually be good for them. Look at it this way: that's what they're telling themselves about you.
  • Cougar Night - Speed-dating for cougars saves time, but why pretend? Just have everyone trade notarized bills of health from the STD clinic.
  • Cougar Cruise - "There are already single cruises and seniors' cruises, so why not combine them?" an unscrupulous travel agent once asked as lightning crashed outside his laboratory. If the boat doesn't capsize from all the no-strings sex, we suggest the yacht be named "The Old Woman & The Sea." We also suggest its bulkheads be painted Purell.

Ben Franklin On (or Under) Older Women

Should you date a cougar? Why don't you let Ben Franklin answer that question? He was not only our wisest Founding Father, he was also our smoothest playboy. When Franklin fathered a whoreson bastard, that child grew up to be governor. When he issued legitimate progeny, a jealous God claimed the glorious baby for Himself.


Through invisible beings which we call angels.

At an age when most men's grandchildren would be dead of old age, he was fighting other suitors and gout with both hands to dip his wick in Parisian tallow, and that was when France had the only women in the world who bathed (once a month, same as now). He was also a master of electricity, the nanotech of the Enlightenment.

Although normally he'd be wearing a fur cap.

All this buildup is so you understand Ben had his pick at all walks of life. And who did he prefer? The Case for An Older Woman answers that rhetorical question. For a dude who preached equality, morality and temperance, he sure could craft a sexist screed. No wonder he was famous for his Maxims.

Kool Ale man!
And for palling around with Kool-Ale Man

Brendan McGinley hands out free comics in New York, and his girlfriend is of legal drinking age.