Summary: Shadowsan is pretty sure he's having a midlife crises. Gray/Black Sheep

Disclaimer: I don't own Carmen Sandiego

Shadowsan mediates peacefully after a grueling day of teaching. It was important he always kept a composed persona—if you're calm, no one can use your emotions against you.

Shadowsan breathed deeply, inhaling the incense around him to steel his nerves. Black Sheep was excelling in her classes like he predicted, but a part of him wanted to curse his predictions. He refused to show weakness like Coach Brunt who displayed her affection for Black Sheep on her sleeve. If he showed he cared, Black Sheep could be used against him, and he would not allow himself to be weak.

Yet, deny it all he wanted, he knew Black Sheep had wormed her way into his cold heart ever since he found her as a baby.

It doesn't mean he can't be grumpy about it though.

Shadowsan inhaled deeply again, trying to clear his head. It would do no good to think about Black Sheep. She brought trouble and discord wherever she went, and Shadowsan would not tolerate that, fondness or not. Black Sheep wanted to be a thief of V.I.L.E—that meant all the light inside her had to be snuffed out.

The thought of the warmth of Black Sheep being doused out disturbed him, but he wouldn't ever admit it to anyone else, least of all to Black Sheep. He couldn't afford to be soft in the lair of thieves.

His thoughts were disrupted suddenly by the appearance of Black Sheep herself. She looked nervous and guarded, unsure if she should approach him, but also determined. Shadowsan allowed her to wrestle with herself for a moment before speaking.

"What is it, Black Sheep?" he demanded, keeping his persona as harsh. Black Sheep didn't flinch. She was used to his tone by now, and she narrowed her eyes, looking at the ground. It appeared she was having difficulty trying to voice her thoughts. "Go on, Black Sheep." He urged, and if she was able to read him, would realize he was asking her gently.

"Instructor Shadowsan, what is a date exactly?" Black Sheep blurted. Shadowsan nearly choked on his own spit, but he held composure. Did he hear her correctly?

"A date?" he parroted, confused and a little apprehensive. Black Sheep looked embarrassed.

"Well… you see, I thought I could ask you because you'd tell me. Coach Brunt wouldn't tell me. Dr. Bellum and Countess Cleo were just giggling at me and Dr. Maelstrom just looked grossed out when I asked them." Black Sheep explained. She had a thoughtful expression. "I don't get why no one will tell me."

Shadowsan told himself to inhale deeply. He told himself it wasn't a big deal. Black Sheep probably found the word in one of Countess Cleo's trashy novels again.

"A date is something between two people who are romantically attracted to each other. They pick a place and time and hang out for a period of time." Shadowsan patiently explained.

"So… it's like between friends?" Black Sheep appeared confused. Shadowsan inhaled again. He was getting too old for this.

"It is for two people who want to hopefully pursue a relationship and eventually marriage, Black Sheep." Shadowsan told her. Black Sheep squeaked then, her entire face turning red. Shadowsan felt a sense of forbidding overtake him, his eyes narrowing. "Why exactly are you asking about dates, Black Sheep?"

"Erm… Gray… he asked me if we could go on a date…" Black Sheep answered nervously, both equally flustered and flattered at the revelation. This time Shadowsan did choke a little, coughing.

He remembers Gray. The boy is quite charming according to the female students. He remembers his excellent stealth work in class, but Black Sheep still excelled at the top of pick pocketing. He recalled the boy, Gray, was always at Black Sheep's side. He had thought it was because they were both lonely, but now Shadowsan realized that Gray had a romantic inclination towards Black Sheep.

Arrogance filled him—Black Sheep was above everyone here. She was too warm and pure to be sullied by criminals. Black Sheep needed someone who was full of light like she was, and not anyone tainted by V.I.L.E. He did not rescue Black Sheep and give her the best life possible only for her heart to be broken by someone shrouded in the darkness like they all were.

"Are you okay, Instructor Shadowsan?" Black Sheep questioned warily, observing Shadowsan's expression as if the man was constipated. The man came back to his senses, and Black Sheep wondered what he was thinking.

"Black Sheep," Shadowsan finally began, "Did you tell him yes?" he asked seriously. Black Sheep, to her credit, appeared flustered.

"I thought he was talking about the calendar to be honest, but then I realized that didn't make sense…"

Of course she told the ruffian yes. Just Shadowsan's luck it seemed. He resisted the urge to pinch the bridge of his nose strongly.

"Do you want to go on a date with him, Black Sheep?" Shadowsan went straight to the point. If she said she didn't want to go, Shadowsan would make sure the boy backed off. However, he internally groaned when Black Sheep was giddy and bashful.

"I… I'd like to go." Black Sheep admitted shyly—very uncharacteristic of her. Shadowsan sighed.

"Very well." Shadowsan said. "When is your date?" he asked.

"Umm he said Friday…" Black Sheep responded. Shadowsan nodded.

"This Friday, you will report to my classroom ready for your date and he will pick you up at 8pm here and return you promptly at ten. If he is one minute late, he will not be permitted to take you on the date." Shadowsan ordered. Black Sheep blinked. "Also, after this, go to Countess Cleo to ask for clothes to wear. For a date, you are expected to dress nice."

"Ohhh… okay. Thanks, Instructor Shadowsan." Black Sheep said, getting ready to leave his classroom.

"After you are done with Countess Cleo, tell Gray that he is ordered to come see me." Shadowsan commanded firmly. Black Sheep didn't argue—this all new territory for her.

"Yes, sir." She said, leaving Shadowsan to his thoughts. The samurai closed his eyes, before opening them with a determined gleam. He walked over to his sword, eyeing it.

Black Sheep was the light of V.I.L.E. The last bit of humanity each of them had left went into raising her. If he was going to allow someone to ask for her heart, he would be sure it was someone who was worthy.

If Gray was serious about Black Sheep, he would have to show it to Shadowsan.