15 Hollywood’s Hottest Cougars

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3) Jennifer Lopez

J-Lo has a pretty rocky romantic history full of divorces and broken engagements (Ben Affleck, anyone?). But maybe it’s just because she was dating men that were too close to her in age? You know, men who weren’t nearly young enough to appreciate the type of woman that she is. Case in point: After separating from ex-husband Marc Anthony, she began dating one of her backup dancers, Casper Smart. And Smart is 18 years J-Lo’s junior, young enough to be her son!

But don’t bank on this starlet continuing this trend of dating much younger people – J-Lo has stated that dating men significantly younger than her makes her feel insecure. You know what makes us feel insecure? Lopez’s choice of movie roles. Sometimes we forget that this is the same cougar that starred in Anaconda, Gigli, Monster in Law and Maid in Manhattan.

So while J-Lo dating young allegedly makes her feel insecure, you’ve got to believe that it also allows her to date people that won’t judge her by her so-so Hollywood career. Casper Smart was only a wee boy at the age of 18 when Gigli was released for God’s sakes!