In October 2010, Oprah was having a run-of-the-mill meeting with her producers when the man of her teenage dreams walked through the door. "Why don't you change clothes and we'll go across the street and get something to eat?" Jackie asks.
Oprah is floored. "Thank God Stedman's in Bermuda," Oprah jokes. "I can't believe I have no lipstick on when Jackie Jackson is here!"
Watch Jackie surprise Oprah