If you were glued to VH1 in 2006, you remember the chaos. The clock necklaces. The spitting incident. The nicknames that sounded like something off a dollar-store snack menu. But mostly, people remember the finale of the very first season when Flavor Flav overlooked the fan-favorite Tiffany "New York" Pollard to pick the soft-spoken Flavour of Love winner, Nicole Woodard—better known to the world as "Hoopz."
It was a massive TV moment.
Honestly, it felt like the entire world stopped for a second when Flav uttered those words. New York was the villain we loved to hate, the ratings goldmine, and the woman who seemed destined to take the crown. Then there was Hoopz. She was athletic, she stayed out of the petty drama (mostly), and she genuinely seemed to have a connection with a man who wore a Viking hat to dinner.
People still argue about whether she was the "right" choice. Did Flav actually like her, or was it a strategic move to subvert expectations?
The Hoopz Factor: Why She Won Season One
When we look back at the first season, Hoopz wasn't the loudest person in the room. That’s probably why she won. While New York was busy reinventing the reality TV villain archetype, Nicole was busy being approachable. She played the game differently.
She wasn't just a contestant; she was a competitor.
You’ve got to remember the context of 2006. Reality TV was still in its "Wild West" phase. Production wasn't as polished as it is now. Flav was looking for someone who could balance out his high-energy, often erratic persona. Hoopz offered a level of chill that the other finalists simply didn't have. She was the "girl next door" if the girl next door had a killer vertical jump and could hold her own in a house full of aspiring starlets.
The chemistry was weird. It was definitely weird. But it worked for the cameras.
But here’s the thing that most people forget about the Flavour of Love winner: the relationship lasted about as long as a commercial break. By the time the reunion special aired, the spark was gone. Actually, it wasn't just gone; it had been extinguished by the cold water of reality. Hoopz admitted later that there wasn't a deep romantic connection after the cameras stopped rolling.
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It was a "show-mance" in the purest sense.
Life After the Clock: More Than Just a Reality Star
Most people win a reality show and vanish. They do a few club appearances, maybe a "Where Are They Now" segment, and then they're back to a 9-to-5. Nicole Woodard refused to follow that script.
She leveraged that win into a legitimate career.
First, she didn't just stay in the "Flavor" universe. While New York went on to star in roughly five thousand spin-offs, Hoopz moved toward fitness and acting. She popped up in movies like Ghetto Stories and Master P's No Limit Chronicles. She wasn't trying to be the next Meryl Streep, but she was working.
Then came I Love Money.
If you want to talk about dominance, look at her run on that show. She entered a house full of VH1 "all-stars" and basically ran circles around them. She won the $250,000 grand prize, proving that her title as the Flavour of Love winner wasn't a fluke based on looks or luck. She was a tactical beast. She understood the mechanics of social engineering and physical challenges better than anyone else on the roster.
She became the queen of the "Celebreality" era.
The Shaquille O'Neal Era and the Public Eye
For a while, Nicole was more famous for her dating life than her reality TV wins. Her relationship with NBA legend Shaquille O'Neal was tabloid fodder for years.
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They were an unlikely pair.
The height difference alone—Hoopz is 5'2" and Shaq is 7'1"—made for some iconic, if slightly surreal, paparazzi photos. They were engaged for a bit. They lived in his massive mansion in Sudbury, Massachusetts. For a moment, it looked like the former reality star was going to become the wife of one of the greatest basketball players in history.
It didn't last.
The breakup in 2012 was messy, at least according to the rumors. There were reports of public arguments and a dramatic exit from the mansion. Nicole didn't lean into the drama, though. She didn't write a tell-all book or go on a press tour to bash her ex. She just... moved on. That's a recurring theme with her. She hits a peak, the situation changes, and she pivots without looking back.
What the Flavour of Love Winner Is Doing in 2026
So, where is she now? If you check her social media today, you won't see much about Flavor Flav. You won't see many throwbacks to the mansion in Encino.
Nicole Woodard has rebranded herself as a fitness mogul and a lifestyle influencer.
She’s heavily involved in the "Hoopz" brand, focusing on health, wellness, and female empowerment. She’s also a producer. She realized early on that the real money isn't in front of the camera—it’s behind the scenes owning the content. She has spent the last decade building a portfolio that has nothing to do with 15 minutes of fame.
She’s an entrepreneur.
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She’s also been vocal about the mental toll of early reality TV. She’s talked about how young women were often manipulated by editors to look "crazy" for the sake of a storyline. As the first Flavour of Love winner, she saw the blueprint being created in real-time. She’s used her platform to advocate for better treatment of reality stars, acknowledging that while the show gave her a start, it also came with a lot of baggage.
Why the Win Still Matters
We still talk about this because Flavor of Love was a cultural reset. It was the precursor to the high-drama, meme-heavy reality TV we see today. Without Hoopz winning and New York losing, we don't get the same evolution of the genre.
It was a study in contrasts.
The win validated a certain type of contestant: the "understated" player. It showed that you didn't have to be the loudest to win the prize, even if you had to be the loudest to get the most screentime.
Actionable Takeaways for Reality TV Fans
If you're looking back at the legacy of the Flavour of Love winner, there are a few things you should actually do to see the full picture:
- Watch the Season 1 Reunion: It is a masterclass in awkwardness. It’s where the "real" Nicole Woodard starts to emerge, distancing herself from the "Hoopz" persona that Flav fell for.
- Follow Her Current Ventures: Check out her fitness programs. It’s a complete 180 from the 2006 era and shows how to successfully pivot a brand after a public peak.
- Compare Her to Other Winners: Look at the winners of Season 2 (London "Deelishis" London) and Season 3 (Thing 1 and Thing 2). You’ll see that Nicole set a standard for "life after Flav" that the others struggled to match.
- Revisit I Love Money Season 1: If you want to see why she's a legitimate powerhouse, watch her gameplay. It’s far more impressive than her time on Flavor of Love.
Nicole Woodard isn't just a trivia answer. She’s one of the few people who survived the "Trash TV" era of the mid-2000s with her dignity and her bank account intact. She played the game, won the check, and then played an even bigger game in the real world.
She didn't just win a show; she won a career.
Most people from that era are trying to get back on TV. Nicole seems perfectly happy just being herself, far away from the clocks and the chaos.