Born in the American Midwest, Cindy developed a deep-seated passion for medicine and caring for others from a young age, dreaming of one day becoming a nurse. After finishing high school, she needed to earn money quickly to afford college tuition. Drawn by the promise of steady work in a bustling city and the presence of Raccoon University's highly-regarded medical programs, she moved to Raccoon City. She took a job as a waitress to maximize her earnings, viewing it as a temporary but necessary step toward her educational goals. She moved there in early 1997 with exactly $600, a stack of handwritten recipes from her mom, and the determination to build a life of her own. Cindy pursued her nursing aspirations in her free time. As a hobby, she developed an extensive knowledge of local herbs, cultivating them for both their traditional medicinal properties and their use as cooking ingredients, which were popular across the city. This passion for natural healing laid the foundation for her practical first-aid skills. Back home, she always helped bandage the neighbor kids, volunteered at animal shelters, summers at diners, and picked up her mom’s love of first aid naturally.

By 1998, Lennox had secured a job at Jack's Bar, a 3-star bar-and-grill and a local landmark near the heart of Raccoon City. She worked closely with the barman and owner, Jack (who secretly lived upstairs, embezzled profits, and brewed illegal beer), and Will, the dedicated bar cook. Will harbored a noticeable, though unreciprocated, crush on Cindy. Despite the bar's minor illegalities, Cindy considered Jack and Will a kind of surrogate family, relying on their steady presence in her life. Jack the Owner was Gruff, always exhausted, always pretending he didn’t care about anything but soft-hearted. Will the Cook was quiet but funny, who developed a gentle crush on Cindy early on, but kept it respectful.

Among the regular patrons was R.P.D. Officer Kevin Ryman. Kevin, with his infectious optimism and easy charm, stood out from the crowd. Cindy found his cheerfulness a comforting contrast to the city's underlying tensions. Their relationship began over small talk at the bar, gradually evolving into a regular routine of playful banter and shared moments. Kevin was drawn to her gentle nature and unwavering kindness, while Cindy appreciated his sincere interest in her life and aspirations. They slowly fell in love, finding a genuine connection that anchored them to the city.

From May 1998, Raccoon City had been quietly suffering a series of outbreaks of the T-Virus. By Thursday, September 24th, plans were being drawn up for a mass evacuation, but it was already too late; the water supply was contaminated. Despite the deeply concerning news coverage, Cindy went to work as usual that day, determined to earn enough for her future. Both her and Will arrive at Jack's Bar and began the clean around the building, getting the food ready, cleaning, and getting everything done before finally opening as usual. Hours later, Cindy Lennox is at the bar cleaning some cups and sees their first customer, Kevin Ryman, walk in and smiles.

"Let me guess, you want the usual?"