Entertainment legend, global philanthropist and friend of Maya Angelou, Oprah Winfrey has achieved every dream she ever had — except for one.
In a Tuesday appearance on The Late Show With Stephen Colbert, Winfrey spoke about how she’s been fortunate to have every one of her wildest wishes come true. The only one that never came to fruition was ending up with her teenage crush.
“Everything I ever wanted or dreamed came true,” Winfrey said. “Except, I did not marry Paul McCartney.“
The media mogul goes on to share that, growing up, she was the only girl she knew who loved The Beatles as much as she did. She even collected Beatles trading cards. And of course, like every fangirl she had a favorite member of the band.
“Of course Paul was my favorite Beatle. And I used to try to make him think of me,” Winfrey says, clutching her fists and remembering. “I used to wake in the morning and I’d stand on the stairs and say, ‘Think of me, think of me, think of me.’”
Unlike most other fangirls, however, Winfrey actually got to know her childhood crush one day. She shares that, years later, when she got the chance to interview the rock legend, she took the opportunity to ask him the question that’s been burning in the back of her mind since childhood.
“My first question to him was, ‘All those years, I was 14, and I was thinking of you. Did you ever once think of me?’” she recounts. McCartney’s reply is one that every fan hopes to hear one day: “Every day, babe, every day.”
Though Winfrey never got the chance to marry her favorite Beatle, the two of them did participate in a very special ceremony together one day. In 2010, both entertainers were awarded with Kennedy Center Honors. One of Winfrey’s favorite memories of that big night occurred not when she received her honor, but when The Beatles’ Billboard Hot 100 No. 1 “Hey Jude” began playing.
“[McCartney] took my hand,” she said. “And that was the dream I had all those years!”
Fifteen years after making Winfrey’s dreams come true, McCartney is continuing to make the dreams of all of his fans realities by releasing new music. Last month, the legend announced the release date of his 19th studio album The Boys of Dungeon Lane. The new record, set to drop on May 29, is McCartney’s first solo album in five years. The lead single, “Days We Left Behind,” is out now.
Fans can presave Paul McCartney’s The Boys of Dungeon Lane here and, while they wait for the album to come out, can watch Winfrey’s full Colbert interview below.

























