Instagram/Oprah Winfrey & Paul McCa Celebrity Oprah Winfrey reveals her teenage dream to marry Paul McCartney. She shares the story of her Beatles fandom and the one wish that didn't come true. April 9, 2026 AceShowbiz - Oprah Winfrey, the iconic entertainment figure and philanthropist, recently opened up about a lifelong dream she once held - marrying her teenage crush, Paul McCartney. In an engaging conversation on The Late Show With Stephen Colbert, Oprah Winfrey reflected on how she has been fortunate to see many of her dreams come true, except for that one special wish.