17. Jenna Bentley and Ben Brown
When it comes to odd couples, nothing beats seeing a bikini vixen frolicking with a much older and completely unattractive sugar daddy.
Pictures of Jenna Bentley and millionaire Ben Brown made headlines a couple of years ago when they first emerged on the Internet. People who struggle to find a reasonable explanation are being silly. It is legal for a gifted Playboy model to hang out with whoever she wants.
Of course, it is love we are talking about here. The kind of love that conquers all differences and which is not shy to show itself to the world.
Well, technically speaking those are paparazzi photo and the two were supposed to be alone on that exotic beach. The same way blood attracts the sharks, an odd couple at work makes candid photographers lose their minds.