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
- Some people find the term "cougar" offensive and would prefer the original nomenclature: "cradle-robbing harlot."
- 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.

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.

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.

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.

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.

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.

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.






For those who need help figuring it out, a cougar is a type of cat, they are females who have pussies, a word that was used to talk about cats, like p***y cat, and they prowl, like a cat, for younger men. Considering men call themselves lions and tigers it's only fair women get their own big cat reference.
Replyyou dont gag at courtney cox ;) everrrrrr
ReplyWho invented the term Cougar, by the way? Why not Saber tooth? I was thinking T-Regina as Regina is Latin for Queen (Rex is King in Latin).
ReplyGo ahead and call any woman a lizard. I f*****g dare you.
I must ask this: why are they called cougars? Why not, say, camels?? Or rhinos?? :)
Reply"Dude, I'm so going to bang that rhino!"
Just doesn't have the same ring to it...
If you imagine the charators in the graduate holding glasses of tea. It is like a tea comercial.
ReplyMILF? I thought that meant Mother I'd Like (to) Fuck.
ReplyOh, and the ONLY good thing about dating _REALLY_ older women? You can do it any time of the month, dudes!
Haha. Gross.
That was the joke.
The first part was the joke, not the menopause part.
Slagging? Didn't know the term was in use your end of the planet. A+.
ReplyChrist I'm patronising.
Matronly Individuals Looking Fetching
ReplyGold. Pure gold. I'm... definitely stealing that one.
"She's crazy, like a bicycle made of babies."
ReplyI am blown away by the sheer awesomeness of that sentence.
"Some people find the term "cougar" offensive and would prefer the original nomenclature: "cradle-robbing harlot." That's f****n hilarious. Oh and the part where he said the comments section usually has helpful spam for where to meet cougars- classic
Welp, I've always perfered younger men, even when I a girl in school. My current boyfriend is 4 years younger than me, which isn't a huge difference (24/ almost 28). Cougars usually border on already being mothers and in their 30's, so I'm all good. ;)
ReplyNot really. The preferred age gap usually grows as you get older. By your logic, a "future" cougar at your age would be hitting on 4 yr-olds. But whatever you want to tell yourself.
nicely done.
ReplyYou haven't seen nicely done yet.
Goddammit, CRACKED. That last picture hurt my eyes.
ReplyCourtney Cox is definitely the hottest MILF ever.
No way dude, definitely Jennifer Aniston :D
that was amazing! i love the talking chicken rings...!
ReplyAh, Cougars. The emotionally wrecked 20-somethings of the early 90's in their latest incarnation. It should be interesting to see these "Cougars" as they morph into actual senior citizens. I'm going to buy stock in mood-pill related companies. That alone should bankrupt Obamacare.
ReplyAh, Trolls. Able to work politically charged rantings into any subject.
It's an understandable mistake, since Courteney only plays a cougar (She's older than her husband, but only by seven years), Demi really is a Cougar, hooking up with 25 year-old Ashton Kutcher whe she was 40.
ReplyDude, that's not Demi Moore. That's the hilariously awesomely named Courtney Cox.
Reply"If the boat doesn't capsize from all the no-strings sex, we suggest the yacht be named "The Old Woman & The Sea."
ReplyWouldn't a better name be "The Old Woman & the Seamen?"
Won't salt on their slimy bits kill them ? Oh sh*t, sorry that was a different article :-/
ReplyIm guessing its from the 5 hardest animals to kill?
'never hit an older woman with more than half your normal force'.... uhh funny but not funny. like, not funny.
ReplyIt's funny because it's funny and also funny.
Crazy women that bang younger men are cougars. Crazy men that date younger women are either rock stars or cult leaders. (same thing really)
Reply