‘I Love New York Reunited’ on VH1: The Highs (and Lows) of The Epic Tiffany Pollard Reunion Special

It’s been over a decade since Tiffany “New York” Pollard sought love on VH1’s I Love New York and it’s very possible that no other reality show personality has quite the loyal fan base that Tiffany does. Her dating show, though it made an actual attempt to help Tiffany meet her match, was a parody of more self-serious shows like it, thanks entirely to Tiffany’s comedic timing and brash personality. ILNY preceded ABC’s The Bachelorette, and legions of New York fans actually spoke out when Rachel Lindsay was announced as the first Black bachelorette, citing Tiffany as the actual first.

Those fans were richly rewarded when – at long last – Tiffany (who is newly engaged now) reunited with several of her former suitors for a quarantine reunion special hosted by Vivica A. Fox, and featuring Tiffany’s mother, Sister Patterson, along with past contestants like Tango, Tailor Made, Whiteboy, and Mr. Boston. On the reunion, which aired tonight (11/23), Tiffany discussed how the show affected her life, which contestants she wishes she kept longer, and of course, where she stands with Flavor of Love‘s Flavor Flav. (Though they don’t often keep in touch, “it’s always love and mutual respect” between them.) In fact, it seems that for all the drama on the show, there’s nothing but love and respect between Tiffany and most of her past suitors. Time does heal all wounds — as long as you show up in person to the reunion, Chance. Here are some of the sweetest moments of friendship and forgiveness, as well as the most awkward disses and digs from I Love New York Reunited.

LOW: Mr. Boston’s Awkward Dig At Tiffany’s Smoking Habit

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Mr. Boston, real name Lee Marks, (real handle, @mrbostoninboston) was dubbed by Tiffany “Best Kisser” of his season. In response to that honor, Mr. Boston, the first guest on Reunited, said, “I’m still worried about gettin’ lung cancer just from making out with her.” And to add to that awkwardness, when asked if he really dated New York’s Flavor of Love arch nemesis, Pumkin, he responded, “I’m allowed to date whoever I want, right?” Overall, Mr. Boston’s appearance on the reunion was best summed up by Sister Patterson’s reaction to him:

“He so stupid,” she later said.

HIGH: Whiteboy’s Mellow Vibe and Long Dreads

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While it was clear that Mr. Boston fell out of favor in real time with Tiffany, Sister Patterson, and even Vivica after making his smoking comment, Whiteboy (Joshua Gallander) was charming from the moment he arrived on the show. Filming remotely in front of his Buddha statue and aquarium in Miami, he greeted everyone warmly before Vivica called out the elephant in the room, his dreadlocks. I mean, it had to be said, we only know him with no hair. When asked what he’s up to these days, his response was, “Mostly a calibration of mind, body and soul.” Got it! Oh, and he was in this Super Bowl commercial too, catch him at the :54 mark next to Pitbull. Namaste, Whiteboy.

HIGH: Tailor Made’s Spontaneous Diss Track Toward Mr. Boston

When Vivica asked Tiffany at the top of the reunion about her engagement to Tailor Made, Tiffany replied, “We really gave it a real shot… I moved in with him but, you know, my attitude got in the way. I ruined that relationship single-handedly.” It’s clear that Tiffany still has love for Tailor Made (a.k.a. George Weisgerber), and when he arrived onscreen, remotely, he performed a rap in her honor. While the first half was a cute ode to their relationship, the second half must’ve been a freestyle he came up with on the fly in response to Mr. Boston’s segment. He rapped, “Yo, Boston, Tiff didn’t deserve that, she’s a queen and Pumkin is wack, if you wasn’t on the show, would she even flirt back?” After the cheers died down, Tiffany explained that Tailor Made really was the one who got away, getting visibly emotional as she told him how responsible she feels for the demise of their relationship. Sister Patterson also had nothing but love for Tailor Made, saying “I’m so glad that I met him, he’s a wonderful man.”

HIGH: Entertainer’s Emotional Journey

The energy in the room was high when Entertainer arrived. Everyone loves Frank the Entertainer and what was even more magical about his appearance was that he went from laughing and joking about sucking Tiffany’s soapy toes one minute, to tearfully paying tribute to his deceased father who appeared on the show the next minute, causing Vivica and Frank to share a somber, strange bonding moment. And then five seconds later the energy was ridiculous again, with Frank screaming “I looooove New York!” Frank is a professional dumpster diver now.

HIGH: Tango and Tiffany’s Roller Coaster Ride Of Forgiveness

When Tiffany’s eyelashes started to fly away on their boating date all those years ago, Tango was there to catch them. And when Tango showed up on stage, he presented Tiffany with the lashes that she thought were long gone. Creepy? Maybe. The kind of crazy we’re here for? Absolutely.

When we last saw Tango in the I Love New York season one reunion episode, he angrily broke off his engagement to Tiffany by telling her off for being disrespectful to him and his mother. On Reunited, he explains that he regrets how he behaved and was too young and hurt to properly express his emotions then. But Tango still had some grievances to air, especially regarding comments Tiffany made about his mother. (While Tiffany denied ever saying anything negative about Mama Tango, the show producers pulled the footage of her saying that his mother was “like a brick wall. Plain and big.”) To his credit, Tango didn’t instigate further, and things even turned flirty eventually, with Tango saying that Tiffany was the one who got away.

LOW: No Chance

One suitor who refused to participate in I Love New York Reunited was the one man that Tiffany regretted not choosing: Chance. When Vivica asked Tiffany about him earlier in the episode, Tiff compared him to Tango, whom she did choose, saying, “He’s the comedian and he’s energetic, and he stroked me in a different way.”

“Literally,” Vivica says.

“Yes, no, literally. We were banging on production’s door for contraceptives when we were in Jamaica or wherever! ‘Cause it got that raw with us. I always wonder what we could’ve been.”

Tiffany was clearly hurt by his absence, saying that it’s like he turned his back on her. “For him not to be here tonight, it feels like he stood me up.”

Tango went one better. “We came here because a real man can say, hey, things didn’t work the way we liked, but we can go show some respect for the queen.” Mr. Boston, who was probably happy that the negative energy was off of him, went even further than that, saying “He is a coward for not showing up.”

HIGH: A Real Honor

Chance’s brother, Real (Ahmad Givens), also a contestant on the show, passed away from cancer in 2015. Real was a genuine friend to many on the show, especially Tango, who read a short note Real wrote him after Real was eliminated from the show. Tango explains that the reason he’s so upset that Chance isn’t present at the reunion is because Real had hoped for a reconciliation between the two men, saying “I came here, aside from showing some respect for Tiff, to make sure the world knew that two black men could be cool and work things out, and that was something that [Real] told me he wanted to see.”

HIGH: Milliown’s Story

One contestant we didn’t expect to see was Milliown (Jamal Trulove), but he was there at Tiffany’s insistence to tell his story. In 2010, Milliown was falsely imprisoned for a murder he didn’t commit for 50 years. After six years, he was acquitted. (Read his whole story here.) Since his release he’s become an advocate for others like him. Though it felt a little out of place to tell such a serious story on a mostly lighthearted show, his story is remarkable.

LOW: Mr. Boston’s Lapdance

Look, I really have nothing against Mr. Boston and I feel bad about piling on here, but when Vivica asked the men of the show if they had any regrets about their time with New York, Mr. Boston said his only regret was that he didn’t give her MORE lap dances. As a result, he performed a fully-clothed, socially-distanced one for her onstage. To that I say – nay, I beg – keep that lap in Beantown, buddy.

Liz Kocan is a pop culture writer living in Brooklyn. Her biggest claim to fame is the time she won on the game show Chain Reaction.

Watch I Love New York Reunited on VH1