NeonHorizon: I can't believe the number of puns I inadvertently had Giran make in this chapter. All puns regarding Kugutsu's name and quirk. Just bizarre. Anyway, I wrote Gray Area, but it got so splintered that I decided I wanted a new story centered on Shigaraki so here's a dark rom-com featuring one of my favorite anime villains ever. Reviews are welcome.

"I want to meet him."

The man paused in counting some money and lifted his gaze, eyes instantly narrowing. He quirked an eyebrow and a lazy sort of smile stretched his mouth. "What are you going on about now?"

"I want to meet him," she repeated. The young woman planted her hands on the desk's surface, her manicured nails shining obsidian in the light. "So…introduce me, Giran-san."

"You don't really want to meet him. Trust me. You're better off just staying in the shadows for now, Kugutsu-chan." Giran shook his head, chuckling as he saw her tap her nails against his desk. "Why do you want to meet him so badly? Do you have a little crush?"

She bristled at this and curled her hands into fists. "I…don't get crushes," she muttered. "You meet with him. So why shouldn't I?"

"Because it's not necessary. Look, kid, you're my trump card. You know how this works. I throw you into the ring when things start to look bad for me. That's just what assistants do for their bosses."

The young woman crossed her arms and frowned. But, technically, your boss is my boss. So why shouldn't I get to meet him?

The man had resumed counting yen notes, but he could feel her icy glare directed at him. His assistant usually had a pretty even temper. She helped him with a large variety of tasks, kept quiet about what they did, and she was efficient. She rarely showed this much emotion and it was honestly a little perplexing.

"You really want to meet him that badly, Kugutsu-chan?"

She gave a small nod. "If I'm your assistant…I need to have the same connections that you have," she pointed out.

Giran held up his hands in resignation. "Fine, fine. I'm meeting with him tonight. Why don't you go doll yourself up before we go? You want to impress him, right?"

To her absolute outrage, she felt her face starting to burn. "That is…not at all what this is about and you know it," she hissed.

"Really, it's so weird to see you get this animated about something that isn't games or gore. It's almost like you're a different person." Giran pushed up his small, round glasses and flashed a smirk. "You're almost like a normal girl."

That was the final straw for her. She turned on her heel and stalked out of the room, hands jammed into her coat pockets. Why does he feel the need to pick on me? I told him that this isn't about a crush. How could I have a crush on someone I've never met?

She was determined to put no effort into her appearance and dressed as she normally did. A pair of tight fitting black pants, a button-up lavender shirt, and her favorite black choker. She left her shoulder-length black hair scruffy and sticking up at strange angles in some places. The only time she really brushed her hair was when she had to play a part for Giran. Whether it was to collect information or to get items for him, she always went all out for her "boss".

The young woman's expectations were rather low from the start. Really, she just wanted to see this man in the flesh. All for One's protégé. His champion. A man around her age with an impossibly dark backstory that made hers look like a bedtime story in comparison.

I shouldn't have built him up with all of that just now. She ruffled her dark hair as she walked beside Giran down an alley, ignoring the way he chuckled. "What was his name?"

"We're meeting with Shigaraki Tomura and Kurogiri. The one that's making your fragile little girl's heart skip a beat is Shigaraki."

"…you have a little heart…" she muttered in retort.

"Oh to be young and in love. What's it like, Kugutsu-chan? You feeling starry-eyed? Seeing the world through rose-colored glasses?"

"I haven't even met him."

They approached the mah-jongg bar and Giran paused, running his fingers through his hair. "Damn. Probably should've brought a gift or something. That'd put him in a good mood, huh?"

"Giran-san?" She saw him frowning and raised an eyebrow. Does he…actually look worried? It was rare for her "boss" to look unsettled, but when he did, he usually called on her to defend him. The young woman cracked her knuckles, mirroring his frown. "What is it?"

"Stop doing that; it's not ladylike." He stepped in ahead of her, calling a greeting as he went.

She hesitated in the doorway, suddenly very unsure of herself. Nervously wiping her sweating palms onto her pants, she took a deep breath. What is there to be nervous about? I wanted to meet him so I can have the same connections as Giran-san. This is business.

"Who is that, lingering near the door?" a low, male voice demanded.

"That would be my assistant. I don't know why she's just lurking in the shadows back there. Kugutsu-chan, why don't you come introduce yourself? You were so eager to meet Shigaraki."

At this, she flushed pink and grimaced. Entering the room like a child being forced to attend a family gathering by their strict parent, the young woman looked to the two strangers. A man that resembled a living shadow was behind the counter and polishing a glass. He was dressed rather formally and his face bore no features except for his narrowed yellow eyes.

Her gaze shifted to the other stranger and her breathing hitched. Giran had not prepared her adequately for this. Shigaraki was around her age, but he was not quite the monster she had been picturing. In fact, he looked a bit weak. Wearing a black t-shirt and sweatpants, he looked more like a NEET than a villain. His pale blue hair was shaggy in appearance, similar to hers, and she had the feeling he brushed it as often as she brushed her own hair.

Bandages were showing on his arms where the sleeves failed to cover his skin and it was then that she remembered the USJ incident. He had been shot in all four limbs by a hero on that day. The young man met her stare from behind curling locks of hair and he scratched his neck anxiously. "Why did you bring your assistant? I didn't even know you had one. Why would I be interested in-?"

"Kugutsu Kurayami, sir." She bowed lowly and tried to settle the blush on her cheeks. "I…actually really wanted to meet you." When she rose from her bow, she caught sight of the man's malevolent smirk and her heart began to pound.

"You wanted to meet me? Why's that?" It almost sounded like he was taunting her.

Before she could speak again, Giran shook his head and pushed up his glasses. "I'm sorry. I'm afraid Kugutsu-chan has a little crush. You know how women get."

What do you think you're doing? The young woman bristled and this time, her pointed feline ears flattened against her head in anger. She rarely showed emotion while doing business. She rarely displayed any sort of outrage in front of Giran because it was deemed unprofessional. Now, she felt that she could tear out his intestines and hang him from the ceiling by them.

Shift P.O.V

A crush? Studying Giran's assistant, he felt a rush of giddiness bubble up. Never in his life had someone said that they had a crush on him. With the poor quality of his skin and his line of work, it just did not make sense for a girl to fall for him. However, this one seemed to be a bit "off".

Scruffy black hair, hanging to her shoulders. A smattering of freckles across her cheekbones. Eyes that were a sharp yellow color like a cat's. This made him look up to the pointed, feline ears atop her head. They had flattened when Giran spoke, but he could see them swivel now to perk forward.

"Are you some kind of villain groupie or something?" he muttered. He knew they existed. They were the same as the girls that sent love letters to serial killers. Kurogiri had once explained that they liked the danger, but would probably recoil if they ever met those men in real life.

"I'm…not a groupie," she protested. Her voice was soft, but kind of low, with a melodic quality to it.

"So why did you want to meet me so badly? Was it just…some kind of morbid curiosity?" Shigaraki got off of his bar stool, ignoring the pain from his injuries. He wanted a real answer. From her; not from Giran.

"No. I just…hear about you from Giran-san."

Kugutsu Kurayami. That's a stupid name. I bet she doesn't even have a quirk. And what kind of slob dresses like that to meet their boss? This last thought stuck with him and his dry, chapped lips pulled into a smirk. "I'm your boss. Of course you wanted to meet me."

"That's right," she agreed.

Giran put a hand on the girl's back and gave her a rough push forward in Shigaraki's direction. "That's right! Kugutsu-chan, why don't you tell him why you were so excited to meet him!"

Now forced to stand about a foot away from Shigaraki, the female villain looked far less sure of herself than before. She glanced over her shoulder at Giran, who was wearing an amused half-grin. "I…I just…"

"You know what?" The man pushed up his glasses and checked the time on his phone. "I have to go run some errands. Shigaraki, it's okay if I leave her with you for a while, right? She can provide some entertainment."

"Wait…" Kugutsu turned to protest, but Giran was already leaving. Sweat beaded on the back of her neck and she hesitantly looked to the other two villains. She bowed, lower than before, and frowned. "I'm sorry about Giran-san."

Shigaraki simply stared for a moment and lifted a hand to scratch his neck. "You wanted to meet me," he reminded her, mirth leaking into his voice. "So why don't you make yourself useful and entertain me?"

Kurogiri took this opportunity to enter the conversation once more. "Giran once mentioned you to me. He said you have an interest in games."

"Games?" Shigaraki's grin returned. "Fine. I'll take you to my room and you can entertain me."