Gregory Chillak’s Job Struggles on 90 Day Fiancé: From Bakery Dreams to Freelance Plumbing
Gregory “Greg” Chillak’s journey on season 11 of 90 Day Fiancé has captured the audience with not only the complexities of love across continents but also with a real-life struggle millions can relate to: the challenge of finding stable employment. As his relationship with Ugandan fiancée Joan Kruchov faces pressure from cultural expectations and financial realities, Greg’s career search has become a focal point, sparking debates among fans about ambition, responsibility, and the cost of the American Dream.
At the heart of the couple’s narrative lies a cultural and financial rift. Joan’s family insists on a dowry—a tradition that demands Greg pays $3,000 as a “bride price.” However, his lack of a steady job has raised significant concerns for Joan’s relatives. “He doesn't take, like, work serious,” Joan confided to her family, raising doubts about Greg’s dedication. Greg, in turn, admitted during a tense exchange with Joan, “I don’t know how he’s really going to pay for the dowry because he's not financially stable for now,” she revealed, clearly uncertain about their future together.
For Greg, the struggle has not just been about finding any job, but carving his own path. With aspirations of opening his bakery, Dough Bro. Bakery, he’s taken to social media to nurture his entrepreneurial dream. Yet, while passion projects are fulfilling, they seldom pay the bills overnight. Amid mounting expenses—including an $8,000 debt from visa and legal fees—Greg had to reassess his priorities.
In a pivotal move, Greg shifted from his bakery ambitions toward a more immediate solution, taking up freelance plumbing work, as reported by Greater Long Island in March 2025. The transition was not without its hurdles. The show documented Greg’s job hunt and his hesitance to take a “state job,” which he turned down, admitting, “I just wanted to be able to spend time with you… I think there’s going to be more opportunities in the future…it’s not necessarily something I was really passionate about.” Joan, increasingly frustrated, issued an ultimatum: “If you don’t want to get a job, I want to go back to Uganda.”
Fans and commentators have dissected these tense moments, debating Greg’s choices—should one pursue dreams or settle for reliability? Is Greg’s story an indictment of American work culture, or simply one man’s reluctance to compromise? As Greg put it, “It’s not just going to be me anymore. It’s going to be we.” His openness about finances and his struggle to adapt invites viewers to consider the true cost of love in a globalized, expectation-laden world.
As 90 Day Fiancé continues, Greg’s evolving job search remains a litmus test for his relationship and his readiness for the next phase of life. Will bakers’ dreams—or plumbing gigs—be enough to bridge cultural divides and financial gaps? Readers, what do you think about Greg’s choices? Have you faced a similar conflict between passion and practicality? Share your opinions below and join the conversation.