May 7, 2024

7 Cougars Who Came Before ‘Awkward”s Jenna Hamilton

For high school seniors, afternoons are reserved for coffee dates with pals, some pick-up basketball down the street or, if you’re Jenna Hamilton, taking the virginity of the sophomore class’ music prodigy. Sorry for partying…?

On last week’s “Awkwardepisode, J-Town, who’s been trying to resist the 10th grader who charmed her on New Year’s Eve, gave in to her temptation and enjoyed an afternoon delight with Owen…only to find out minutes later that he was a virgin. Jenna was totally caught off guard — and a bit sickened by the fact that she suddenly felt like a shameless cougar.

Sure, sleeping with Owen may not have been her finest moment, but Jenna isn’t the first lady to enjoy a fling with a younger guy. Below are seven ladies who did just that. Some channeled their inner cougar on the big and small screens, while others did it in real life — but they all serve as proof that Palos Hills’ favorite blogger should be proud of her prey:


Jules Cobb

On “Cougar Town,” Courteney Cox’s character found the love of her life in the comparably aged Grayson, but before the couple’s love story began, Jules was queen of the jungle. Teaching her dates to kiss was just part of the usual routine, but she didn’t mind!


Stifler’s mom

Stifler'sMomGetty Images

Not only is the “American Pie” character the single origin of the term MILF, Stifler’s mom proved she was a cougar when she seduced one of her son’s friends, Paul Finch, and made his after-prom party one he’d never forget. As her famous line goes: “I got some scotch. Aged 18 years. The way I like it.”


Taylor Swift

TSwiftGotcha Images/Splash News

John Mayer was 13 years Taylor Swift’s senior when the two music stars dated between 2009 and 2010, but T. Swift proved she could rob the cradle too when she was linked to Robert F. Kennedy’s grandson Conor, who’s a good four years younger.


Rachel Green

The silver spoon-fed “Friends” character ultimately wound up with Ross, a scientist who was a couple years her senior. But in the middle of the show, Jennifer Aniston’s character shacked up with Tag, whom she’d hired to be her assistant. Tag’s hobbies included riding on scooters and giving thumbs-up.


Samantha Jones

To be fair, the “Sex and the City” character dated dinosaurs and zygotes alike, but the fortysomething PR executive had a particular eye for twentysomething dopes. Still, peek inside any trendy Manhattan restaurant, and you’ll see plenty of the same.


Jennifer Lopez

JLoCasperXavier Collin/Celebrity Monitor/Splash News

She and Casper Smart broke up in June, but for two years, J. Lo enjoyed the company of her former backup dancer — who’s nearly two decades her junior. LOVE KNOWS NO BOUNDS, OK?!


Mrs. Robinson

The cougar of all cougars, Mrs. Robinson went after her friends’ 20-year-old son in the classic 1967 movie “The Graduate.” Does it look like she felt a hint of shame for her seduction, Jenna? LIVE YOUR LIFE.

About the author  ⁄ Matthew Scott Donnelly

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