Cindy, before her makeover

5 of 12
Cindy, a 44-year-old mom, says she hasn't changed her look in almost a decade. Not only are her clothes from last century, so is her hairstyle. She admits that she's been sporting the same French hair roll since the '90s. Plus, she sleeps in her makeup every night.

"What are your pores saying to you?" Oprah asks.

Tim thinks it's time for the real Cindy to shine through her foundation. "I saw you yesterday without any makeup, and you looked fabulous," he tells her. "[You're] naturally gorgeous."