Drew Carey and Megan Martinez (5/15)

Out of the celebrities who have dated adult stars, Drew Carey, host of The Price Is Right, has had one of the most successful relationships. After Drew broke up with his fiancée Nicole Jaracz in 2012, he and Megan Martinez met on the adult webcam site Myfreecams.com. After sending her some gifts he met her in person in Las Vegas at the Adult Video News Awards. He soon flew her and her nine-year-old son out to his Hollywood mansion, then bought the two of them a home and started paying for everything in their lives. Drew intends to stay with her, but will not marry her until her webcam career is over, as he does not want other people seeing his wife naked. He is often referred to as her sugar daddy, which makes sense seeing as he is worth $165 million!