Bayleigh Regina Pelham’s journey to finding love and success took an unexpected turn following a series of personal setbacks. After losing her job and ending a long-term relationship, Pelham sought a fresh start by auditioning for Season 11 of the television show "Big Brother Canada." She relocated from Halifax, Nova Scotia, to Toronto in preparation but was ultimately cut from the cast just before filming began. The decision was reportedly due to the presence of another former boyfriend also cast in the show, necessitating her removal.
In the aftermath, Pelham decided to take a solo trip to Sayulita, Mexico, in March 2023, intending to spend time alone and reset. A friend traveling there introduced her to Stephanie Cassano, a Toronto-born bar manager and aspiring firefighter. The meeting sparked a powerful connection between the two women, despite Pelham’s previous relationships being exclusively with men. Over several days, their friendship deepened, culminating in an emotional exchange of feelings on the eve of Cassano’s departure from Mexico.
Although Cassano was in a relationship at the time, the pair agreed to pause contact temporarily but planned to reconnect once Pelham returned to Toronto. Upon reuniting at Cassano’s workplace, Locals Only, their mutual attraction reignited. Despite initial reservations—including Cassano’s ongoing relationship—they soon made a commitment to explore their feelings fully. Cassano separated from her partner shortly thereafter.
Pelham, a content creator and actress with credits including commercials for Google and WhatsApp, moved back to Toronto in April 2023, where she resumed bartending at Paros Yorkville. Cassano, 36, had recently completed fire and emergency training and continues aspiring to a firefighting career. The couple quickly became inseparable, solidifying their relationship with a memorable date on April 30 and an official engagement during Toronto Pride in June 2023.
Following their engagement in January 2025—marked by a surprise proposal during a family gathering—Pelham reciprocated with a proposal during their photo shoot the following month. The couple wed on September 5, 2025, at Wheatfield Estate in Sparta, Ontario. Their ceremony reflected a blend of personal and familial significance, with a best friend officiating and an ordained minister overseeing the legal formalities during a private first look.
The black-tie celebration combined rustic Italian influences with modern elegance. Cassano wore a custom ivory suit crafted by her relatives from Calabretta in Woodbridge, Ontario. Pelham chose two gowns, including an off-white satin dress by Alexandra Grecco and a second look—a 1920s-inspired lace and fringe dress designed by her mother. The event brought together 140 guests, symbolizing the merging of their families and communities.
In a notable postscript, Pelham returned to television as a contestant on Season 12 of "Big Brother Canada," which aired from March to May 2024. She won that season, underscoring a personal and professional turnaround following earlier disappointments. Her former boyfriend, who remained on Season 11, was the winner of that season.
Together, Pelham and Cassano continue to build their life in Toronto, living in a home owned by Cassano’s parents, openly celebrating their relationship and shared future.