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While the Inbox is a bit annoying (each message takes up a whole new slot, instead of filtering down and combining them), Cougar Life is where I had the most luck in talking to people, and actually connecting—and really, that's the biggest factor here.​​ More » Slightly more expensive than some other sites on this list ($15.55-29.95/month; free for cougars), and missing any sort of live-time chat options, this site does boast an eye-catching, slick layout with many fun features.More » There are a few similarities between higher-ranked Date ACougar and Cougar Fling: the pricing ($13.33-29.99/month), and oodles of search features, for starters.Cougar Fling does, however, a much better job of laying out the site and making it easy to use, yet has so few members—most of whom live in the US—that it's barely worth your while to sign up.In a nutshell, you buy a month-long membership and then will need additional credits to do anything of use on the site.The site is well laid out and modern, and it's likely the most well-known of the cougar dating sites because of ​its extensive media coverage (yet only has 500,000 members).More » As the only 100% free cougar dating site that I could find with enough members (800,000 ) for a potential match, Cougared got some major bonus points right off the bat.