Oprah Winfrey, a name that has long been associated with generosity, wisdom, and inspiration, is now facing criticism for what many are calling a tone-deaf response during a recent viral TikTok moment. The clip, which quickly spread across social media, showed the media mogul interacting with a fan, Colin Drummond, in a conversation that struck many viewers as deeply out of touch with everyday financial realities.
Drummond had approached Winfrey, expressing his desire to find a meaningful gift for his ailing mother. Winfrey, famous for her annual “Favorite Things” list, suggested a high-end jewelry box that had recently been featured in her collection. “That jewelry box that I had on ‘Favorite Things,’ you know, is a wonderful thing,” she told Drummond, according to reporting from the New York Post. However, Drummond quickly responded, “It’s too costly for me.”
That’s when the conversation took a turn. Oprah replied, “No, it’s not—it’s really not,” seemingly dismissing his concern. Drummond, who works for TMZ, clarified that the jewelry box cost over $100, and he was searching for something more affordable and sentimental. “Less than $100,” Oprah said, visibly surprised. Drummond then explained that his mother preferred heartfelt gifts rather than expensive ones.
“Oh,” Oprah responded, “Well, then this is the ideal gift for your mom,” suggesting he make a list of the top ten reasons he loves his mother and create a heartfelt card. While the suggestion itself was kind and thoughtful, many social media users couldn’t ignore the way she had initially reacted to the idea that $100 might be too much for someone to spend.
One commenter wrote, “The judgment when he said $100 was too expensive,” capturing the sentiment of many viewers. Another sarcastically added, “Oh, are you poor? I have a better gift idea for you.” Others mocked her reaction, saying things like, “She was shocked to learn that $100 was too much. Do they even make things that cost less than $100?”
The online response was swift and unforgiving, with people accusing Winfrey of being out of touch with the financial struggles many Americans face. “She’s lived in her own world for so long where money isn’t an issue that she’s lost touch with reality,” one critic said. Another added, “Oprah spends over $100 on every meal. She has no sense of what real people go through.”
Much of the backlash stems from the public’s growing frustration with wealthy celebrities who, knowingly or unknowingly, seem disconnected from the average person’s experience. Oprah, whose estimated net worth stands at $2.6 billion, lives an incredibly luxurious life far removed from everyday concerns like gift budgets and price tags. Her primary residence, an estate in Montecito, California, is named “The Promised Land” and spans multiple properties she purchased over time to expand her private paradise. The main house features a chef’s kitchen, ten fireplaces, a large dining room, six bedrooms, and fourteen bathrooms.
As reported by Vogue, she even had a separate house constructed on her property solely for reading the New York Times while sipping tea. In addition to her Montecito estate, Oprah owns homes in Hawaii, Florida, New Jersey, Nashville, and Chicago—each offering its own luxury and privacy.
Her lavish lifestyle also includes private air travel. Back in 2015, Oprah purchased a $75 million private jet, citing a moment at the airport when a fan asked for a hug as the tipping point. The jet now allows her to travel between her many homes in comfort and privacy. While there’s nothing inherently wrong with enjoying wealth, her recent interaction highlights the gap between that lifestyle and the struggles of the average person trying to afford basic items or meaningful gifts for loved ones.
Many Americans, especially those in the middle class, are growing increasingly wary of celebrities who appear out of touch while continuing to publicly express political opinions or dispense life advice. Oprah has built an empire on empathy, storytelling, and connection, but this recent incident serves as a reminder that even the most admired public figures can miss the mark when they forget the daily challenges many people face.
Whether this moment becomes just a passing controversy or a more lasting reflection point for Winfrey remains to be seen. But one thing is clear: in a time when financial insecurity is very real for millions, even well-meant advice can come off as insensitive when it lacks awareness of what life is like for those outside the celebrity bubble.
