But this time, their talk about Lauren's life, career and commitment to cancer causes will be done in front of a sold-out crowd of arts patrons at Lincoln Center and a celebrity guest list expected to include Jerry Seinfeld, Martha Stewart, Tom Brokaw, Naomi Watts and Anna Wintour.
Proceeds from the event will benefit Lauren's cancer care center in East Harlem, along with Lincoln Center itself.
Produced by Tony Award winner Darren Bagert, the multimedia presentation reinforces the Upper West Side venue as a fashion-industry destination. It's where most of the city's designers - although not Lauren - present their seasonal collections at New York Fashion Week.
Meanwhile, Mayor Michael Bloomberg declared Monday as The Ralph Lauren Center for Cancer Care and Prevention Day.
Winfrey was expected to wear a custom-made gown by Lauren.
Back in May, Lauren told Winfrey during their televised interview that he considered becoming a baseball player, a basketball player, a cowboy, a dancer - even Batman - before settling on fashion as his livelihood. He said he was drawn to Batman because of "the ability to stay young, the ability to enjoy what you enjoyed when you were a kid, not to give up the hope and excitement."