Tiffany Pollard’s relationships have always been televised creating some of reality TV’s most iconic moments. But with her current engagement, she’s chosen to do things differently – keeping it private. Before we dive into her relationship, let’s take a look back at her previous showmances.

TV Icon Tiffany finally found the real love, she’s been searching for.(Image: Charles Sykes/Bravo via Getty Images)

Celebrity Big Brother star Tiffany ‘New York’ Pollard, 43, has never been shy of the spotlight. From her iconic meltdowns to unforgettable one-liners, she made reality TV history – especially during her 2016 stint in the CBB house, where she brought chaos, unexpected flings and even the unforgettable ‘David’s dead’ moment that fans are still talking about to this day.

She even made an appearance in this years’ Celebrity Big Brother special – Late and Love, where she was a part of the celebrity panel revisiting the show’s drama. But one thing she’s keeping more under wraps is her mystery fiancé. The star revealed she was engaged last year during an interview with Jason Lee, where she shared a few details about her partner. She explained her fiancé is Jewish and had just turned 58 at the time, but the rest stayed secret.

Tiffany appearing with her first showmance Flavor Flav(Image: @tiffany_hbic_pollard/instagram)

Tiffany’s other romantic connections have been far more public. From a young age, her dating history became part of her brand after she rose to fame on the iconic love sow – Flavour of Love, starring Public Enemy’s Flavor Flav where 20 women competed for his heart, and Tiffany, just 23 at the time quickly became a fan favourite for her charismatic, unapologetic personality. But in the end, Flavor chose another participant Nicole ‘Hoopz’ Alexander over her.

However when Flavor’s relationship didn’t go as planned, he decided to go for season 2 of Flavor of Love, when he called Tiffany back to eliminate some of the new participants. When he asked her to return to the show to fight for his heart, the pair drew closer than before and even became intimate, but once again he chose another contestant.

Despite things not going to plan with Flavor Flav, the reality show opened doors for Tiffany to have her own spin off, ‘I love New York’ where just like Flavor of Love, men competed for her heart, giving us an even deeper glimpse into her crazy, unpredictable love life.

Her love life has always been wild but now things changed swiftly(Image: Shutterstock)

Patrick ‘Tango’ Hunter won against 20 contestants to be with Tiffany. Tango stood out with his smooth talk and sensitive side, separating him from the rest. He ‘proposed’ at the end of Season 1 and Tiffany said yes. But at the reunion, he caused a scene by dramatically dumping her on stage after seeing disrespectful comments Tiffany made about him and his mother during the show. The shock separation left her feeling blindsided and heartbroken but it also left the door open for season two.

In season one, two other men made their mark – brothers Ahmad ‘Real’ and Kamal ‘Chance’ Givens. They had completely different personalities and brought a mix of charm, chaos and humour. Both made it far, reaching top three however in the end Chance wasn’t picked, after she decided to move forward with Tango.

Tiffany revealed she made a mistake in Season 1(Image: Getty Images for MAC Cosmetics)

After the show, Tiffany admitted she regretted not choosing Chance. Years later, a tragedy hit the news that Real had passed away in 2015 after battling colon cancer.

Since the relationship with Tango didn’t last , I Love New York returned for another season. This time, Ezra ‘Buddha’ Masters became a standout finalist. He was tall, intense and unlike her previous favourites. He was eventually eliminated for his temper, but Tiffany asked for him to return.

In the end it was George ‘Tailor Made’ Weisgerber who won her heart. He was perceived as a nerdy, polished contestant but he was persistent and determined to win Tiffany over and it worked. She chose him in the final, and the pair got ‘engaged’ at the reunion special before living together in Queens for a while. However, the relationship quickly ran its course.

Tiffany and her Season 2 pick, Tailor Made(Image: Getty Images)

Moving away from American reality TV, Tiffany starred in Celebrity Big Brother – bringing her flirty, bold personality across the world. While in the house, she made her interest in Geordie Shore’s Scotty T clear. They shared kisses and flirty moments, but it soon became cloear he didn’t quite feel the same spark.

But Scotty wasn’t her only crush in the CBB house. Tiffany also boldly confessed her attraction to another housemate, Darren Day, telling him “You’re so sexy… I tried to deny it, but you’re just so masculine.” However as Darren was married, he reminded her of his marital status, leaving a little awkwardness in the air.

In November 2016, Tiffany appeared in another reality show – Famously Single. The show brought celebrities together to work on their relationship problems, but almost instantly sparks flew between Tiffany and Gladiators’ David McIntosh. On the very first night, she made a bold move, instantly inviting David to the bedroom. And he didn’t hesitate. However their relationship was brief and there was no sign of a continued relationship after the show.

Tiffany and Scotty T shared passionate kisses in the Celebrity Big Brother house.(Image: REX/Shutterstock)

More recently, Tiffany has opened up about her sexuality. “So sometimes, I’m not gonna lie, I feel like a guy. Sometimes I feel like a woman,” she told The Jason Lee Show last year. “I don’t want to fight it. I just want to be who I am when I wake up that day.”

Lee then asked Tiffany about her personal definition of queerness, and she said it was “someone who embraces both sides, and whatever that feels like for me that day or in that moment, I’m gonna live it.” When asked if she’d ever slept with a woman, Tiffany coyly giggled and said: “What do you think?”

Now she’s all loved up with her mystery man. She first announced their proposal during the I Love New York reunited special back in 2020, where she shared that it had happened only a few days prior. Since then, she’s opened up about how this relationship isn’t the same as her past drama filled romances.

Last year, she spoke to US Weekly about their relationship, revealing their bond is different than her past lovers, “Like, that’s my soulmate, and I’ve never felt like that before,” she said. “He’s so perfect for me. And that was a journey to get there though.”

“I’ve always gave another lip to somebody else or left a little flap open, if you will.” she added (Image: ITV)

While she still hasn’t revealed his identity yet, Tiffany hinted that she envisions a small, intimate ceremony in Paris. It’s her dream but not everyone is as thrilled – especially her mum.

“I mean she wants the big full one because I’m her only daughter. So of course the mother’s gonna want that. But I want something small. I just want to eat a hot dog, rock the wedding ring and then just be in Paris somewhere staring at the Eiffel Tower,” she said

Through all the showmances, Tiffany never stopped searching for real love and it seems she may have found it.