Penelope observed the blonde huntsman through the interconnected web of cameras made to observe every street and alley of Atlas. Despite the sophistication even this surveillance system was limited, there was no camera in Jaune Arc's dorm room which he shared with two others, Lie Ren and Nora Valkyrie, his teammates as she had eventually learned, combing over the digital files Bonnie had provided to her.

It had only been a couple of days but already she was noticing a slight pattern to his movements. Twice already he had woken up earlier than his comrades to fly to mantle where he followed a familiar path through the city visiting various homes and apartments collecting about a half dozen children and their mothers whom he escorted through the school. A quick data search found an ongoing low level huntsmen contract that he had picked up regularly and it seemed since the chaos of the recent terrorist attacks had died down he had resumed taking the contract regularly. The rest of the day had been more sporadic with him preforming various duties for Atlas or working higher level contracts with his teammates, he regularly interacted with another team of four similarly aged girls whom a data search revealed to be Team RWBY led by Ruby Rose, potential enemies.

But what interested her the most was watching her sister. Penny was not the easiest to track, unlike Jaune she moved around the city with far greater speed and efficiency thanks to her flight capabilities, tracking her with cameras that mainly resided on street level was far more difficult and a pattern was hard to discern. But what she had seen her do was curious, she had watched her fly in after two vehicles had collided injuring the occupants, she had observed her sister use her enhanced strength to pull apart the warped metal to retrieve the injured human inside and apply medical aid ahead of the paramedics. She thwarted petty robberies by very simply subduing and bringing the criminal in. She had pulled civilians from burning buildings and assisted fire crews however she could, she had even helped bring a cat down from a tree.

It was wrong. They were weapons, instruments of destruction not tools for whatever it was she was doing. They were built to kill, Vasily had told her so. Was her sister simply defective as a weapon? Was she confused with her purpose? The sight of it gave Penelope a strange unfamiliar feeling, a powerful desire to correct her sister. Was this anger? That emotion she had only witnessed from Vasily, was this what he felt when Bonnie forgot her place?

Many of the things she witnessed through the digital lenses of the cameras made little sense to her and others made her curious to what they meant. Some things she dismissed as simply strange things for humans that didn't apply to her. The one thing that kept entering her mind was from when she had first located Jaune leading those children to that school. Her sister had met with him there and after a brief conversation they had brought their faces together touching their lips to one another. It seemed a strange gesture to her, she did not know it's significance but it seemed strangely important to her and she made a note to bring it up to Vasily.

She caught sight of Jaune Arc leaving his dorm room in the Academy dressed in his usual manner and walking the halls to the nearest landing pad where she had already observed Penny waiting for several minutes.

It had seemed odd that she would wait for a bullhead when she was perfectly capable of flight herself but upon seeing Jaune step onto the pad and smile in her direction it became clear that she was waiting for Jaune. They came together and once more touched their lips together if only for a brief instant. What was that? Some sort of human thing she had yet to understand? It seemed significant unlike other moments where she watched him scratch certain parts of his anatomy or disappeared for irregular periods of time into bathrooms.

She watched as he took her hand in his interlacing their fingers together and bored a bullhead together.

Penny grinned as Jaune greeted her with a peck on her lips and took her hand. Kissing him had become familiar but every time it still sent a surge of happiness through her.

"So what's the plan for tonight?" Jaune asked, he helped her step aboard the bullhead. "We haven't really planned anything out."

"I was thinking we could figure it out as we go along," She suggested sitting next to him and resting her head on his shoulder, the simple proximity and physical contact far more pleasing than she could have guessed. "Are you hungry right now?"

"A little," he answered her idly looking out the window as they passed over the city.

"What would you like to eat?" she asked him.

"I was actually thinking you should pick dinner," Jaune suggested.

"I do not not eat Jaune," She reminded him.

"I know but you like asking me about the flavor and the experience, I was thinking maybe you would like picking out someplace to eat and then asking me questions on the food," he explained to her.

"That… sounds fun," she said honestly. Food was one pleasure that she wished she could experience, the way it seemed to dominate everyone's day to day lives and how everyone seemed to experience flavor differently fascinated her.

"Do you have anywhere in mind?" he asked her cracking a grin her direction as the bullhead touched down and they departed taking to the streets of Mantle hand in hand.

She took a moment to consider her options. His suggestion made her think of dozens of restaurants or food trucks she regularly had passed by patrolling the streets or overhearing others speak about their favorite places to get lunch or dinner. Curious as she was about the numerous dining establishments she at least wanted to be somewhat considerate of Jaune and not have him consume anything he did not like. "Do you like barbeque?" She asked him, thinking of a rather popular spot not too far from their location in easy walking distance.

"I love it," he told her, "I cannot remember the last time I had a good kebab or ribs," he explained to her, "It sounds perfect."

"Then I know this place I have heard mentioned before," she explained to him leading him down the street and cutting through an alley.

The place was a small little dive with a simple neon sign reading Smoke N Grill with a picture of a pig out front.

"I would not have noticed this place just walking by," Jaune explained to her looking at it curiously.

"That is what I found interesting about it," Penny explained to him, "It seemed rather indistinct despite the apparent praise and popularity it has."

"It's a hole in the wall," Jaune said.

"A what?"

"A hole in the wall," he repeated, "Usually a small indistinct restaurant with usually great food," he explained.

Penny nodded, "yes I suppose it is," she said unclear as to why one would refer to a place like that. She led him inside and she heard Jaune take a long audible whiff of the air.

"Oh man I'm getting hungrier just smelling it," he said to her.

"Table for two?" A waiter asked them, stepping up with a couple of laminated menus in his hand.

"Yeah," Jaune told him, letting him lead them to a booth laying down the menus for each of them.

The waiter asked if they wanted anything to drink which Penny naturally declined, Jaune ordered a water and a cup of cola. They were left alone to overlook the menu.

"What looks good?" Penny asked him scanning her own menu with everything from grilled chicken to custom pulled pork sandwiches.

"All of it," Jaune answered her, "You know more about this place than I do, what is it particularly known for?"

"I have overheard mention of this place having remarkably good ribs and kebabs." She answered him thinking back to her times patrolling the area overhearing people outside talk about what they had enjoyed best.

"Well they have mini kebabs and I'll do a half rack of pork ribs," he declared, setting his menu down. In moments the waiter was back and he placed his order, Penny felt a little strange not ordering anything but Jaune didn't seem bothered by it.

He chuckled a bit looking at the napkins to their side, "it's a good thing I didn't wear my suit," he told her with a grin, "I'd probably mess it up eating here."

Penny nodded looking down at her usual green and white dress, "The General said I needed to remain ready in the event of another serious emergency, that means I have to remain in my combat clothes," she explained.

Jaune nodded, "It's probably for the best," he told her, "I'd hate to have another incident where I needed to call my locker to my position, changing in the street was not exactly comfortable."

"Still… I am a little disappointed," she confessed to him, "I was looking forward to dressing up for you," she explained, "I was actually planning to shop for something to wear but I did not have the time to and since I am supposed to remain ready for combat there didn't seem to be much point."

"We could shop after dinner," he suggested to her, "find you something to wear for the next date."

Penny smiled at that, "I feel very pleased that you are certain there will be another date," she told him, "even as we are just beginning our first."

"Why wouldn't there be a second?" He asked.

"It is not that, it is simply that it shows that you are comfortable with us, with this. You said you wanted to give us a try but you seem really sure of everything right now," she explained.

He smirked a little at that, "I am comfortable," He assured her reaching across the table to take her hand, "I don't know if I'd say I'm sure about everything but so far this has been nice," he told her squeezing her hand.

The waiter arrived with a small place of several small kebabs, sharp wooden skewers through pieces of grilled meat and vegetables sizzling fresh from the grill. Jaune picked the first one up biting up a piece of steak and a plump steaming mushroom, he chewed and made a noise of approval.

"How's it taste," Penny asked him, eager to hear his description.

Jaune finished chewing and swallowed before grinning at her, "Where do I begin?"

Penelope watched as both her targets sat in the restaurant together sitting across with animated conversations between the two. It seemed tedious to her, watching and waiting on a human to consume sustenance. What was the point of this?

The camera mounted in the restaurant gave her a limited view of them and she extended her search fanning her perception out to the surrounding areas taking sight through more to the areas outside the simple establishment where her sister was wasting her time with the Arc boy.

Outside the rest of Mantle was busy descending into it's nightly routine that she hardly cared for or understood. Vasily had instructed her to look for consistencies or patterns and she tried applying that to the surrounding areas but it all seemed like chaos to her with the humans moving about with little consistency and what little consistency she saw seemed irrelevant to her.

An unmarked bullhead crossed the lens of a single camera and pulled her attention. She had seen it before yesterday and again now flying in a circular pattern in the city above. She supposed it might be easy for a human to miss, especially if they were not observing the skies like she was but with the complex air traffic between Atlas and Mantle the craft seemed to be flying aimlessly around a couple thousand meters about Jaune Arc's current position.

That was interesting, a single bullhead in the skies could easily be amiss but now it stood up obvious to her as it maintained a flight pattern keeping it close to the Arc boy. Was he being tracked or followed?

She noticed the bullhead pulling away to break from it's flight path, setting a new course directly for Atlas as another unmarked Bullhead flew in and took its place continuing the flight pattern that their previous craft had left off. That was interesting, they were maintaining a vigilant watch of him with alternating shifts. That was certainly something to tell Vasily."

Jaune patted his stomach in contentment looking at the pile of rib bones, stained napkins, and an eaten ear of corn all in front to him.

"Would you like any desert?" The waiter asked him.

"No I'm stuffed," Jaune told him, "we'll just take the bill."

The waiter nodded and excused himself to bring them the bill. "I will admit I was looking forward to hearing you describe ice cream," Penny told him.

"I could," Jaune told her, "put then I might have to describe vomiting to you as well."

Penny giggled, "In that case I will pass."

The waiter returned and Jaune paid for the food and they left walking out into the night. "Shopping next?" Jaune asked her, "I'm pretty sure that mall we went to for my suit isn't very far from here," he commented realizing how familiar this city was becoming to him.

"Yes it is only a few blocks this way," Penny said pointing down the street. They walked outside together hand in hand.

"When we went shopping for that suit," Jaune said, "Did you like me back then?" he asked.

Penny nodded.

Jaune scratched the back of his head, "I'm sorry," he told her, "I had no idea… that could not have been very pleasant."

"No do not apologize," Penny said, "I was happy to help you back then, and honestly I should have confessed sooner."

"Still though," Jaune said, "that had to be rough."

"It was a little at first," she admitted, "but after you told me about Pyrrha I realized how important that date was for you and now after everything I do not know if I would change anything given the chance. I was very jealous of Neon back then but now I am actually quite grateful to her."

Jaune smirked, "Yeah that was a bit of a surprise," he admitted to her, "getting asked out definitely blindsided me but I didn't expect her to turn around and play matchmaker on me."

Penny nodded and gave his hand a little squeeze as they reached the mall entering it together.

"So where would you like to shop?" Jaune asked her.

She shrugged, "I do not know, I have never shopped here before, I do not often shop for clothes."

"Well what do you usually like to wear besides your combat clothes?" he asked her looking at her usual dress, honestly besides the one time in her room and going dancing he couldn't recall her ever wearing anything besides her combat clothes.

"Not much," she confessed to him, "I do not have much space for clothes and I am usually on patrol anyways."

"Well then this is a chance for a new wardrobe," he said, giving her a grin and gripping her hand tightly, "so let's go a little crazy, I'll be your packmule."

"I am perfectly strong enough to carry my own bags Jaune," she told him, "there's no need for you to burden yourself on my behalf."

He chuckled, "I know that," he told her, "but I want to, I know it might sound silly but I was always told that's what a guy is supposed to do on a date, maybe it's cheesy but I kind of like the idea."

"Alright," Penny said, "You can carry my bags for me. Where should we go first?"

Jaune looked around at the numerous clothing shops seeing that he had no idea. He quickly averted his gaze from a lingerie shop with lace clad mannequins, there was no way he would be presumptuous enough to suggest going in there.

"Is there anything you feel like you need?" he asked hoping her input would narrow things down, "you already mentioned dresses so I see a place for formal clothes, what about summer wear or maybe even a swimsuit?" He felt himself blush a bit when he realized he asked her about going to look at swimwear. Why was that embarrassing? She is his girlfriend, isn't that normal for a couple their age?

"I do not swim," Penny told him, "so a swimsuit would be pointless."

"You don't swim?" he asked her.

"I am not buoyant like you," she explained, "I sink quite easily."

"Oh, well then let's just start with some dresses for you," he suggested.

They entered in and began rummaging through the racks of women's clothes for her gathering what articles they liked.

"Do you have a favorite color?" He asked, "I usually see you wear green and it looks good on you."

"I am fond of green," she admitted finding a satin green blouse with copper colored buttons that seemed to match her hair, "but I am open to trying on whatever colors you think I would look good in."

Jaune looked at the arrangement of clothes, "well they say black goes with everything," he said, finding a black romper on the rack, "and I remember you wore a grey dress back at Beacon," he said pulling a grey shirt dress off the rack.

They took their assembled clothes back to a changing room and Jaune took a seat waiting for her as she disappeared into the changing room. She didn't take very long changing before she exited the room wearing that black romper he had pulled off the rack.

"How do I look?" she asked him.

"Amazing," he answered truthfully.

"Really?" she asked, turning around, it was backless exposing her shoulder blades as her curtain of copper red hair moved.

Jaune nodded, "trust me, I'm buying it."

Penelope had observed her two targets all night together, she had tracked them from the restaurant to the mall where they had gone to numerous clothing stores but only her sister Penny had bothered trying anything on and it seemed the Arc boy had contributed to a number of the purchases.

Was this boy like a pet to her sister? She had observed it before, humans on the streets with animals they kept on leashes. There seemed to be no reason for this aside from the amusement of the humans and she could not help but draw a similarity to this phenomenon, or perhaps it was like how Vasily was with Bonnie, a superior being keeping another close for practical uses as well as sentimental.

After watching her change into a mirriad of clothes and display them for the boy they had left the mall and returned to Atlas Academy where currently they had stopped in a recreation room to sit on a couch and watched a television together, now it seemed the boy was asleep and her sister kept his head resting on her lap looking rather pleased with herself.

What was special about this human boy? Vasily claimed he was dangerous and masterful but she saw no sign of that, but then again neither had Vasily before being apparently defeated. She had hardly seen him fight in the last couple of days and that had only been grimm that he dispatched with moderate efficiency. But her sister too seemed to find some value in the boy, something she had yet to understand herself. And those unmarked bullheads still kept themselves above his position tracking his every movement. What made him special?

Content that nothing more of interest would be found at the moment she retracted her perception away from the interconnected web of CCTV cameras and found herself back in the simple safehouse.

"Did you find anything?" Vasily asked her.

She turned to find him sitting in a chair with a book in hand and a steaming cup of tea on the table in front of him. Bonnie was asleep on the couch nearby.

"I think so," Penelope told him. The laptop glowed to life as she sent her thoughts through the cable still jacked into her skull bringing up images she had attained throughout her time tracking him.

"I have noticed that there is an unmarked bullhead maintaining a continuous flight pattern above our primary target's location, there at least two trading off in regular shifts." she reported.

"He's being guarded," Vasily said, stroking his stubbled cheeks, "I see, Ironwood likely suspects that he is now a prime target, that certainly makes things interesting. Continue to track those bullheads, try to figure out who is on board. Is there anything else?"

"I have some questions," Penelope told him, "out two targets spend quite a lot of time together," she explained to him, "I am not quite sure how to define their interactions."

"Oh?" Vasily said, "then show me."

The laptop screen changed as Penelope projected her recorded memories giving tiny glimpses to the two's night together, them touching their lips together, their time in the mall where the human sat while her sister displayed a number of clothing articles to him, to the last thing she saw of them together on the couch her sister running her fingers through the hair of the sleeping boy while his head rested on her lap.

Vasily stood up from his chair and approached the glowing screen. He chuckled, "gotten yourself a little sex doll huh Mr. Arc?" he sneered.

Sex doll? Penelope did not know what he mean at all. "Is this useful to us?" she asked him.

Vasily grinned, "very useful, very useful indeed Penelope."

Wow this story is now over a hundred thousand words long, I honestly did not think it was going to be this long when I first started writing it. Hope you are all still enjoying it and enjoyed watching Jaune and Penny's first official date together. Please review and leave you thoughts and opinions. As usual I would like to thank MidKnightMoonglow99, MajorBrony95, Firefly25, and DrknssRules1 for all their help and contributions to this story and those that have not yet been written thank you all.