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Updated Mar 06, 2025The Same 'Bling Empire' Couple Got Engaged Again
Read on for more details about the first proposal.
Courtesy of Netflix
In early 2021, the country binged a reality program on Netflix called Bling Empire. With its unwavering presence gracing the top 10 carousel of Netflix's most popular shows, the series captivated millions of viewers: Bling Empire, based on L.A.'s very own "Crazy Rich Asians" (much like Kevin Kwan's popular bestselling books-turned-blockbuster rom-com) showcased the inner lives of real millionaires; some, in fact, billionaires.
Similar to 2018's Crazy Rich Asians, there was a proposal in Bling Empire, but it didn't involve Henry Golding's character popping the question on a plane with a massive emerald ring. The TV proposal, in fact, was challenging to sit through. The couple's relationship was met with such an outcry of criticism that viewers wondered whether a second proposal would even take place. On Monday, August 30, the time finally arrived for Jessey Lee to propose to Cherie Chan, resulting in the couple's second engagement.
According to People, the furniture empire heir popped the question at the Jacquemart-André Museum. Lee commissioned a painting to pose the question. "I've wanted to propose to Chérie on multiple occasions," he said. "First time was in [the] Maldives, but Chérie was extremely pregnant and I wanted to do nothing but take care of her."
"The second time I had planned a family trip to propose to Chérie under the cherry blossoms in Tokyo, but her mom was really ill. So I postponed the whole engagement," he added. "Although Chérie had proposed to me, I'm glad I got to propose to her now. It's something I've always wanted to do but the timing wasn't right." Read on for more details about the couple's first proposal.
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Cherie and Jessey's First Engagement
The pop star and Lee had been in a five-year relationship before she decided to take matters into her own hands. Together, Lee (the heir to a furniture empire and is supposedly worth $250 million) and Chan have welcomed two children. She delivered her second during the show. The show was filmed, pre-COVID-19, and it documented Cherie mourning her mother, who passed away from cancer. On Bling Empire, Jessey was described as a doting dad, at times "stubborn." He's also referred to as a "trust fund baby."
While counting her blessings, the profound familial loss forced Cherie to confront something else that's missing in her life: marriage. After five years of dating, she was abundantly clear that she was ready for Jessey to propose. The problem, however, was he didn't or he would simply avoid the conversation.
Courtesy of Netflix
When the 100th day birthday of their son, Jevon, rolled around on-screen, Cherie decided the party was the ideal time and place to propose. Wanting to take matters into her own hands, Cherie hatched a plan knowing Jessey would be miffed. In some ways, the Bling Dynasty engagement could've been viewed as a feminist opportunity, where a woman intentionally bucks societal gender norms and pops the question on her end first. But it wasn't because Jessey seemingly wasn't on board with Chan pushing the notion of an engagement.
When the proposal scene arrived, producers focused intently on Jessey's expression as Cherie gets down on one knee. In one shot, he grimaced in shock as his partner looked to him in suspense. There appeared to be a long pause, which could've been impacted by editing, but there was obvious hesitation and it was unclear whether Jessey would storm out or say yes.
Sensing the awkwardness, the Bling Dynasty cast attempted to dispel the discomfort with cheers of support. (It makes it worse.) After what felt like eternity, Jessey said yes as he planted a kiss on Cherie.
What was even more confusing when the series debuted was that the show was filmed pre-COVID, presumably in 2019. Yet, Lee's comments in early 2021 raised lingering questions. "Well, we definitely are still engaged," he told TheWrap in January 2021. "But I still have plans to give Cherie a proper engagement though. That is coming. With COVID it can be a little tricky… But I'm hopeful sometime this year—as COVID settles down with the vaccine—maybe the opportunity for me to actually come through with what I've had in my mind: the perfect proposal for Cherie."
Courtesy of Netflix
"This is all kinda a surprise to me!" Cherie added in the same interview. "I didn't know he was planning on proposing since I already did it. Yeah, that'd be great if he did actually. We've just been doing our daily thing and we never really talk about it so it'd be great if he had something up his sleeve."
There was a momentary sadness for Cherie, who's wanted a proposal for so long, yet her partner wanted it on his own timing. There's somewhat of a compromise, but it's not what both parties wanted. Viewers couldn't stop talking about the Bling Dynasty proposal because while, sure, each couple is unique, it seems these two characters weren't communicating about their relationship wants. And to be clear: the blame didn't rest on Cherie, who previously broached the topic of an engagement repeatedly with her boyfriend. Perhaps a second season of Bling Empire will help reveal why Jessey finally decided it was time to get engaged (yet again).
