Tiffany 'New York' Pollard Remembers All the Men She Loved and Lost On National Television

Image: Array

Over the course of 13 months during 2006 and 2007, Tiffany Pollard was dumped on reality television dating shows three times. She took the first rejection on the chin, exchanging an upbeat goodbye with her new ex, Public Enemy star William “Flavor Flav” Drayton Jr., before driving off in a waiting limousine—where she burst into tears. The second break-up, after she returned to the VH1 series to compete for his heart again, was rougher, and ended in a shouting match. Pollard flashed her thonged bottom, showing Flav just what he would be missing, before once again being whisked off in the backseat of a limo, crying and vowing to piss on his grave. The third breakup, during the reunion episode of her own spin-off series, was most dramatic of all. Security had to intervene to restrain Pollard from her new now-former beau.

“Hearing those words, ‘Your time is up,’ she tells Jezebel. “It still rings in my head.” But from a TV beginning that could have been dismissed as a prolonged experiment in public humiliation, Tiffany “New York” Pollard has built one of the most enduring careers in reality television, all the while becoming a meme queen with a digital second life in countless group chats and Twitter replies. And on Monday, VH1 is airing a reunion of her first star-making vehicle, I Love New York. Fifteen years ago, Pollard set out to find love on TV. Instead, audiences fell in love with her.

After being scouted on an L.A. street, Pollard was selected for the debut season of Flavor of Love, a raucous take on The Bachelor that starred the Public Enemy hype man and Surreal Life alum as its titular singleton. The show, which inspired copycats and spin-offs including Rock of Love With Bret Michaels and Charm School, fairly reveled in its disdain for its young female contestants. Rather than learning hopefuls’ real names, Flav rechristened them, with multiple young women earning nicknames inspired by the shapes and sizes of their breasts and nipples—which is exactly where Flav adhered their name tags.

Out of the near-constant feuds and fisticuffs, Pollard, dubbed “New York” because she hails from Utica, emerged as whip-clever and instantly unforgettable, a chain-smoking anti-hero. Offering cutthroat assessments of every other competitor (“You look like a fairy princess that resides over the pits of hell,” she told one) and determined to stir all possible pots, she laid out her approach to the competition during one now-famous clash: “I might be a fucking bitch to the heart, but at least I don’t smile in all these girls’s faces. Because you are a wolf in sheep’s clothing. I’m not, I’m a fucking wolf.”

“When I was on Flavor of Love, it was just frantic panic mode,” Pollard now says of those combative days. “I always had to fight to get some time with him.”

After making it to the finale of the show’s first season, where Flav ultimately chose Nicole “Hoopz” Alexander, Pollard was brought back for the series’ second outing, only to be left at the horological altar once again. She subsequently fronted her own series, I Love New York, which gave her two more chances to find love, this time choosing her own winners from among dozens of men.

Pollard isn’t prone to breaking reality TV kayfabe, and has long explained that she was genuinely attracted to Flav, a faded rapper 23 years her senior, for his personality. And on her own show, she seemed to genuinely appreciate many of the men. Among the suitors for Pollard’s heart were aspiring musicians (Kamal “Chance” Givens and his brother Ahmad/“Real,” one of the show’s most loveable figures, who died of cancer in 2015), a Harvard Law-educated attorney (David Otunga, who would become a professional wrestler and wed Jennifer Hudson after his run on the series), and a man who would be falsely arrested for murder within months of his brief run on the show (Jamal Trulove, who was framed by San Fransisco police and served more than six years in jail before his exoneration).

“When I did I Love New York and I was now in the driver’s seat,” says Pollard, “it felt so good. I was the bomb. I had to make tough decisions as far as eliminations go, but I could breathe and really look for love and just have space to do it without fighting all the time.”

The constant dramatics featured on Flavor of Love and I Love New York—the backstabbing, the fights, the tears, all over days-old relationships—is a natural consequence of the format, says Pollard. “You have no phone, you have no internet, no paper. You don’t know what’s going on in the outside world. The fact that those things don’t exist, you are going to invest more time into what you’re there to do, your journey, which is looking for love.” One date in the reality TV hotbox, she estimates, equals about 10 in the real world.

At the end of season one, Patrick “Tango” Hunter, who sported jauntily cocked hats and was mocked by his rivals for supposedly resembling a Ninja turtle, won Pollard’s heart. He proposed—then dumped her at the reunion show. She still wonders what might have happened had she selected Chance, his runner-up, instead. Her relationship with season two’s winner, George “Tailor Made” Weisgerber, fared better. Like Pollard herself during her Flavor of Love years, he was the contestant the other housemates loved to hate, and after the finale abandoned the reality TV dictum against seeing each other before the reunion episode in favor of moving in together. But that relationship didn’t last, either.

Weisgerber was “the one person I did want to see the most” at the reunion, says Pollard. “We really did try to give it a shot. When I saw him, it was just like stepping right back into old times.”

It’s impossible to take in this merry-go-round of romance, drama, and heartbreak without wondering about the authenticity of it all. As with most reality TV series, the behind-the-scenes choreographing is only lightly hidden. Still, contestants were constantly scrutinized for signs of fakeness, for suggestions that they were there to promote rap and modelling careers, or were putting on for the cameras. It’s a perplexing vision of legitimacy: On reality TV, being “real” means actively denying the state of affairs and donning a mask of private citizen naivete despite the fact that you’re living in a cardboard mansion strewn with cameras. During her search for love, Pollard gamely slipped on the banana peels the shows’ producers threw out—but also seemed to deftly plan her falls. Flavor Flav gave Pollard the nickname that would become famous. Everything else, she made herself.

The Of Love era eventually yielded to a new, more aspirational style of reality TV, one that would focus on the already wealthy—glamorous housewives, pro-athletes and their families, and of course, the Kardashians. The contents of wine glasses would fly, rather than clumps of hair. And a pathway would emerge for those who do seek romance on shows like Love is Blind and Love Island, one leading directly from elimination night tears to social media influencer status.

But before the script for transforming reality TV appearances into longer-term work was etched in Instagram stone, Pollard was able to transform her wit and flair for dramatics into a career that brought her across the pond for shows like the UK’s Celebrity Big Brother and Ex-On the Beach. These days, she hosts the VH1 interview show, Brunch with Tiffany. And though she’s involved in less bomb-throwing than in her Flavor of Love days, Pollard still manages to go viral, whether she’s prematurely mourning the death of fellow CBB housemate David Gest or standing up for dark skinned black people in the wake of colorist remarks.

And now, the woman who made a willingness to bare almost all about her love life the foundation for one of reality superstardom is fairly mum about her romantic life. “I’ve dated throughout the years. I kept it to myself,” she says. “I was never in the public eye with it and be like, ‘Oh, this is my new suitor. This is who I’m with.’ Anything you bring to the limelight, it’s not going to be easy.”