an assistant's dilemma: a kendall roy & roman roy love triangle

chapter 3

"You're late," Kendall informed Lucy irritably when she entered the office the next morning.

"No I'm not, it's still three minutes to 9:00," she responded, handing him his latte.

"Mm," he replied, taking the coffee without saying thank you. "Do you still know that divorce attorney?"

Lucy sat down in a chair in front of Kendall's desk. "Oh um...yeah. My college best friend's dad is a big time divorce lawyer. Tim White?"

Lucy had studied political science and journalism at NYU and had befriended many rich kids and socialites who were not all that different from the Roys. Her closest friend Eloise's father was known throughout the city for being a hard-hitting divorce lawyer.

"Yeah I've heard of him," Kendall said. "Get me an appointment."

"Do you um...do you know if Rava's gotten a lawyer yet?," Lucy asked, avoiding her boss's eye and feeling guilty for prying.

"Yes, she told me this morning."

This morning. Lucy could only assume that the two had slept together and that Rava had dropped this bomb on him before leaving his apartment.

"I'm sorry Ken," she said, looking up at him. 

He nodded solemnly and took a sip of his coffee. "Do you have plans Friday night?"

Lucy was supposed to go on a first date on Friday night with a guy she met on Hinge. She had dated the same boy for three years of college, but they broke up shortly after graduation, and since then, her love life had consisted of flings, failed first dates and dating apps. The guy from Hinge was more likely than not a douchebag. He was a tall brunette investment banker who was five years her senior, nearly a carbon copy of every man she had swiped right on in the past few years. She could predict how their date would go almost down to a tee. They would meet up at some upscale bar with $30 signature cocktails where he would talk too much about himself and his work while asking very little about her. If he was the perfect amount of cocky that made him somewhat charismatic, she would agree to a second date. However, she got tired of repeating this same pattern, and she was sure whatever Kendall had planned for Friday night was far more interesting.

"No, why?," she asked.

"Want to come to the RECNY ball with me?"

The RECNY ball was Waystar-Royco's annual gala fundraiser, characterized by its black-tie attire, red carpet photos, expensive champagne and food courses, and Logan's famous speeches. Lucy had never attended one; only high level executives were invited. She had only seen pictures in magazines and heard stories from Ken.

She furrowed her brow and held his gaze. "Do you think that's appropriate?," Lucy asked. Her goal wasn't to be condescending; she genuinely didn't know. Her knowledge of the event was very limited, but she assumed it would probably be frowned upon for the CEO to bring his assistant as his date.

Ken shrugged dismissively. "I'm the boss. No one else gets to tell me what's appropriate. C'mon, it'll be fun."

His insistence on her attending the event with him made Lucy smile. "Okay yeah, I'll go." 

•••

Lucy and Eloise met up on her lunch break that day.

"I need a favor," Lucy told her best friend.

"Only taking me to lunch to ask for a favor? I'm offended," Eloise joked with a smile, taking a sip of her iced tea. Her engagement ring shone in the sunlight pouring through the window as she held the glass of tea. Eloise was getting married in the spring, and wasn't the first of Lucy's friends to do so. She couldn't help but feel behind in life.