Robert Mitchell wasn’t just the owner of one successful sports bar---he was the mastermind behind the Game Time Grille franchise, with locations in multiple cities. Known for its electric game-day atmosphere, sizzling bar snacks, and the striking orange-and-black uniforms worn by its waitstaff, Game Time Grille had become a staple for sports fans across the region.

But Robert, now 42, had noticed some troubling trends in recent months. Employee turnover was rising, and customer satisfaction reports showed inconsistencies across different locations. To address the issues, Robert decided to do something unconventional: he would go undercover as a waitress to understand his employees’ experiences from the ground up.

To ensure no one recognized him, Robert chose a Game Time Grille location in a city where he was virtually unknown. He rented a modest apartment for the week, adopting the persona of “Roberta Michaels.”

Robert had always prided himself on his sports bar’s success. The vibrant orange-and-black uniforms, upbeat staff, and casual vibe made it a local favorite in every city it was in. But despite its popularity, Robert sensed that his team wasn’t as happy as they appeared. Employee turnover was increasing, and whispers of discontent reached his ears. Determined to understand their struggles, he devised a bold plan: spend a week undercover as one of his waitresses.

This meant embracing every aspect of the role: the orange shorts, the pantyhose, the sneakers, and even makeup. With his assistant manager Kelly as his co-conspirator, Robert prepared to trade his usual office attire for the uniform of his staff.

Kelly had no intention of letting Robert take shortcuts. “If you’re going to do this, you’re going to do it right,” she said, handing him a bag containing shapewear, a wig, and a uniform.

First came the padding and shapewear to give him a more feminine figure. “The customers will notice if you don’t look the part,” Kelly teased as she adjusted the padded hips and stuffed the T-shirt bra. Next, she helped him into the snug U-neck T-shirt and bright orange shorts, which clung to his newly enhanced silhouette.

The transformation wasn’t complete without the wig---a shoulder-length, feminine style---and a pair of glasses to help obscure his identity. Finally, Kelly applied a natural yet slightly thick layer of makeup to hide his stubble and blend into the dimly lit bar environment.

When Robert looked at himself in the mirror, he could hardly believe it. “I can’t believe this is me,” he muttered, adjusting the wig nervously.

"You know with all that makeup, not only to you not look half bad, you look half your age."

"Yes funny."

"I'm not kidding."

"OK, now, to begin your employment here, you'll have to fill out the paperwork."

"But..."

"Everyone has to do it, and if you don't the other employees will notice. He'll need a timecard to clock your working hours just like everyone else."

Robert filled out an application under his new alias, Roberta Mitchell, listing fabricated details like a fake address and prior work experience. He even signed the bar’s employee handbook, agreeing to the same terms and conditions as everyone else.

Due to the physical nature of the job, Robert was also required to get a medical checkup which would attest to his physical fitness for the job.

“Well, Roberta,” Kelly said with a grin, “welcome to the team.”

Robert’s first day began like any other new hire’s. He attended an onboarding session led by Kelly, shadowed a seasoned waitress named Megan, and learned how to navigate the bustling bar floor. The dim lighting of the bar worked to his advantage, making it easier to blend in, but the fast-paced environment was overwhelming.

His first big test came when Megan told him to take a table on his own. “Remember to be bubbly and flirty,” Megan reminded him, adjusting her own ponytail. “Smile a lot. Be playful---it works for tips. I’ll be right here if you need me.”

Robert straightened his wig, plastered on a smile, and approached a table of two men in sports jerseys, their eyes glued to the game on the TV above.