On the premiere episode of Dating Naked, two daring singles, Joe and Wee Wee, each go on three romantic, adventurous, tropical dates in the hopes of making a lasting connection. But if they want to find love, they'll have to bare it all! Joe and Wee Wee will try their hand at body painting, boogie-boarding, sea tubing, bird-watching and even zorbing in a giant hamster ball. Relationships will be forged and feelings may get hurt...and they'll do it all completely naked.