It started with a single word: "Vintage." When Deon Cole sat down with The Breakfast Club in late 2024 to promote his Netflix special OK, Mister, he had no idea that a casual comment about his dating preferences would turn into one of the most talked-about celebrity "ships" of the year. He was busy explaining his love for "vintage women"—specifically women over 40 who have their lives together—when the legendary Stephanie Mills basically manifested herself into the room.
The clip went nuclear. You've probably seen it. Stephanie Mills, the voice behind "Home" and a legitimate R&B icon, walked through that door like she owned the building. She didn't just say hi; she planted three very real, very unscripted kisses on a visibly stunned Deon Cole.
Since then, the internet has been obsessed. People are asking if they’re dating, if they’re "endgame," or if it was just a masterclass in chaotic energy. Honestly, the reality is a mix of mutual respect, playful flirting, and a lesson in how to handle a legend.
The "Vintage" Comment That Started It All
Deon Cole has never been shy about his preference for mature women. He’s 53 now, but he’s been vocal for years about how younger women often lack the "wisdom and experience" he’s looking for. During that fateful interview, he described older women as "vintage," clarifying that it wasn't a diss but a high compliment. He likened them to a classic car—refined, valuable, and better than the new models.
Then, the universe peaked.
DJ Envy poked fun at the timing, shouting, "Miss Mills heard vintage and walked right in!" The chemistry was instantaneous. Stephanie Mills, at 67, looked incredible and exuded the kind of "main character energy" that most influencers would kill for. When she greeted Deon, the comedian—who usually has a comeback for everything—lost his ability to speak. He was genuinely flustered.
💡 You might also like: Birth Date of Pope Francis: Why Dec 17 Still Matters for the Church
Breaking Down the Kiss
It wasn't a "polite" Hollywood air-kiss. It was three distinct, warm kisses. For a few days, social media was convinced we were looking at the newest power couple in Black Hollywood. But let’s look at the facts. Stephanie Mills has always been a firecracker. She’s a woman who knows her worth and isn't afraid to take up space.
In subsequent interviews, including a sit-down with VladTV, Deon doubled down on his admiration. He agreed with the description of her as a "spinner" (a term for petite, fit women) and recounted the moment with a mix of awe and humor. He didn't shy away from the physical contact; he embraced it.
Is There a Secret Romance?
Whenever two high-profile Black celebrities show even a hint of affection, the "dating rumors" machine starts spinning at 1,000 RPM. In this case, the fans were rooting for it. There’s something deeply satisfying about seeing a comedic heavyweight like Deon Cole paired with a vocal powerhouse like Stephanie Mills.
However, as we move through 2025 and into early 2026, the "relationship" seems to be more of a legendary friendship fueled by a viral moment. Neither has confirmed a serious romantic involvement. Instead, they’ve used the momentum to celebrate one another.
Deon has continued his streak of success, hosting the 56th NAACP Image Awards in early 2025 to rave reviews. Meanwhile, Stephanie Mills remains active on the touring circuit, proving that her voice hasn't lost a single note of its power since her Broadway days in The Wiz.
📖 Related: Kanye West Black Head Mask: Why Ye Stopped Showing His Face
- The Age Gap: At roughly 14 years apart, they actually fit Deon's "vintage" criteria perfectly.
- The Vibe: They share a specific kind of Chicago/East Coast grit and humor.
- The Public Perception: Fans have dubbed them the couple they "didn't know they needed."
Why This Connection Matters
This isn't just about a funny interview clip. The Stephanie Mills and Deon Cole interaction tapped into a larger cultural conversation about ageism in Hollywood. For a long time, women in the industry were treated as if they had an expiration date once they hit 40.
By calling Stephanie Mills "vintage" and treating her like the ultimate prize, Deon Cole flipped the script. And by walking in and owning the room, Mills reminded everyone that a legendary career and undeniable confidence are the ultimate aphrodisiacs.
It was a win for "grown folks." It wasn't messy, it wasn't a "clout chase" for a TikTok trend, and it wasn't forced. It was just two people at the top of their respective games showing out.
The VladTV Follow-up
When Deon spoke to Vlad, he touched on the "spinner" comment. It's a bit of "guy talk" that some found cringey, but in the context of their interaction, it was clearly meant as a testament to Mills' timelessness. Deon noted that he’s dated women much older than himself in the past, citing the wisdom they bring to the table as a major draw. He’s basically the unofficial spokesperson for the "Age is Just a Number" club.
What’s Actually Happening Now?
If you’re looking for wedding bells, you might want to hold your breath. As of early 2026, Deon is focused on his skyrocketing career—juggling stand-up tours, acting roles, and hosting gigs. Stephanie Mills is focused on her legacy and her son, whom she frequently speaks about with immense pride.
👉 See also: Nicole Kidman with bangs: Why the actress just brought back her most iconic look
But they remain "tapped in." They follow each other, support each other's projects, and occasionally drop a comment on social media that sends fans back into a frenzy. It's a "flirt-ship" for the ages.
Most people get it wrong by assuming every viral kiss equals a marriage license. Sometimes, it’s just two icons recognizing each other's light. Stephanie Mills didn't need Deon Cole to validate her, and Deon didn't need a viral stunt to sell tickets. That’s what made it feel authentic. It was a "real recognize real" moment that happened to involve some very public smooching.
Insights for the Fans
If you're following this story, don't look for a formal "we're dating" Instagram post. That’s not their style. Instead, watch how they speak about age and attraction in their work.
- Watch the OK, Mister Special: You can see Deon's mindset on relationships there. It explains why he reacted the way he did to Mills.
- Listen to the Music: If you only know Stephanie Mills from the memes, go back to the Whatcha Gonna Do with My Lovin' era. You’ll understand why Deon was starstruck.
- Follow the Interviews: Both are incredibly candid. They don't have PR teams filtering every word, which is why we get gems like the "vintage" conversation in the first place.
Whether they are a couple or just "industry besties," the impact is the same. They’ve given us a blueprint for how to age with grace, humor, and a little bit of swagger.
To stay updated on their actual projects, check out Deon's latest tour dates or Stephanie's performance schedule. They are both more active now than they’ve been in years, proving that the "vintage" label is actually a badge of honor.