The train ride to Chicago was quieter than Sweetie Belle thought it'd be. As the stops passed by, more and more people got off and he was the last person onboard by the time Chicago approached. The town was more quaint than what he was expecting. Looking down at his list of questions, Sweetie Belle began to plan out his trek for the day. Although there wasn't much, the places turned out to be farther apart than he had expected. He should probably visit the police station, as the boys seemed to have a bad history with them and as much as he didn't like the idea of running into the people who had probably done more harm than good, they might have more of an idea on what their life was like here. The orphanage was also important for similar reasons, so maybe he'd go there afterwards? Sweetie Belle scratched his head. This was harder than he thought.

Sweetie Belle strolled about the town. Maybe getting a small bit of an overview would help him decide where to go first? Despite how small the town was there were still a good amount of people out and about. Some were laughing, another group was chatting off to the side. His ear twitched as he caught some of their words.

"A black cat? Peh, just what this town needed."

"I know right? And you would think it'd get better after that darn demon left!"

The demon they were discussing was no doubt Bendy. From the little he had heard from the boys, Sweetie Belle knew that Chicago didn't contain the most open minded people. But this? This was ridiculous. People got over the whole 'black cat' thing ages ago!

Sweetie Belle quickened his pace, not wanting to hear anymore of the nonsense. Even as he settled on his first destination he could still hear them. It was mostly coming from the elderly, grant it, but still. He wondered if Bendy had to deal with this the whole time he was here. He pushed open the doors to the police station, catching the eyes of a pig at the desk.

The pig glanced towards Sweetie Belle, his snout scrunching up. "Do you need help with something?"

Sweetie Belle shook his head. "No, I think I'll be alright," The officer scowled at him but Sweetie Belle looked away, his eyes scanning what he could see from the front.

It was quite small - a far cry from what you would see in Toon Town. The desks had loose papers poking out from every direction, pencils and pens scattered all over the table tops and post it notes haphazardly strewn onto shelves and cabinets. There was even a freshly split coffee cup on one of the desks, soaking papers that dripped onto the floor. Nobody seemed to be paying attention to it.

Shifting his focus back to the officer, Sweetie Belle noticed how unkempt he was as well. Parts of his uniform had clearly never been ironed before and his attempt at tying a tie was just pitiful! Are these really the people the town was entrusting their safety to?

Sweetie Belle took out a notebook and quickly jotted down a few things. After Sweetie Belle deemed he had seen enough he left the station and headed towards the orphanage.

The orphanage was bigger than the police station. The paint on the walls had grayed and started to peel. It was even cracking in some places. Vines were growing all over, a bit overgrown but still not something to be too concerned with. Well at least this looks like a decent orphanage. Though knowing that Bendy and Boris had to run away from this place on multiple occasions does not give Sweetie Belle high hopes for it.

Entering the orphanage he is greeted by a young toon lecturing some children.

"And this is why we don't have…" Her voice trailed off as she catched Sweetie Belle standing in the doorway. She gave him a quick smile before returning to the children. "To bed. Now."

"Whaaaat?" One of the kids whined. "It's not even 3:30 yet…"

"Play with some toys near your beds then," She hushed them, "Go, go," The kids walked away with grumbles on their lips. She walk towards Sweetie Belle with a beaming smile. "Hello sir! Adopting a child, today?"

Sweetie Belle gave a polite smile, his eyes looking around at everything he could see. He had a feeling he wasn't going to be in here too long. "Actually, I wanted to talk to the caretaker of this place but," He looked at her. She was too young, there was no way she was the person he was looking for. "Are you…?"

She shook her head. "Just an assistant. I can call if you'd-?"

Sweetie Belle waved his hands. "It's fine - it's not that pressing." Yes it was. But if they were like the rest of the people in town, with how they treated Bendy, they might not be forthcoming at all.

"Then I assume you'll just be looking around?" the assistant asked.

Sweetie Belle nodded, that seemed to satisfy her as she left him alone afterwards. After confirming that she was occupied, Sweetie Belle began to take in his surroundings in more detail. Unlike the station, the orphanage seemed much more organized. As he walked in the direction he saw the children went, he saw an empty hall with only the occasional toy or book proper against the wall. Aside from some faint whispers, it was quiet. Too quiet. Weren't there more kids here?

Taking note of this, Sweetie Belle took out his notebook once more and wrote down his observations. The assistant was clearly not pleased with this as she quickly ushered him towards the entrance upon seeing him stash the book away. She might've thought he was press at that point.

Sweetie Belle glanced at the clock on the wall before he the door closed behind him and it pulled him out of his thoughts. He needed to get going. This meeting was something he couldn't afford to be late too.

He began jogging as he took note of the buildings passing by. Soon enough he arrived at his destination - The Dancing Lady.

Sweetie Belle walked into the club. The whole place seemed to be decorated for some sort of event. Hearts were strewn about on streamers and banners, there were heart shaped candle holders and other decals and even some of the employees had some sort of heart on their person. He thought it strange but he didn't comment on it, his eyes catching the person he came here to meet. The owner of this fine establishment stood by the bar talking to their bartender. Spotting the cat, she said a few more words to the man before gesturing Sweetie Belle over.

"Glad to see you made it here safely! Sweetie Belle right?" Diamond Tiara greeted, "Why don't you sit down?"

Sweetie Belle nodded, taking a seat in one of the bar stools. There were very few people there - just a speckling and an older man at the very end of the bar counter. He'd come at a good time. "Hey," He smiled. "Slow day?"

Diamond Tiara huffed good naturally. "Hardly. We're not in the rush period yet. Don't see many folks drinking while the sun's still out." She turned to him. "If you hadn't called me the other day I'd think it odd to find you in Chicago. We're not exactly a famous town."

"Really?" Sweetie Belle asked, brow raised. "Not even after all the news of the bbros in the papers?"

Diamond Tiara shook her head. "Sure there are people who come here for that, but not as many as you think - and I haven't had any ask me questions," She gave him a look, "Yet."

Ah, she already knows. "So I can cut to the chase then?"

Diamond Tiara clinked a glass down beside him, a hand on her hip. "I'd be mad if you didn't." She turned, picking through bottles. "What'll it be?"

Sweetie Belle furrowed a brow. Well, that was contrary to her statement. "Ah, I don't-"

"On the house."

Sweetie Belle relented. "...Water?"

Diamond Tiara glared at him.

"Fine - a chocolate fizz wizz. Happy?"

Diamond Tiara hummed as she began preparing his drink. Sweetie Belle fished out his notebook and placed it on the counter.

Diamond Tiara raised an eyebrow when she saw it, "You prepared a list?"

"I wanted to be ready. I only have so much time after all," Sweetie Belle answered slightly flustered.

Diamond Tiara hummed as she handed him his drink.

"Well let's start with this one," Sweetie Belle looked down at his notebook, "Are the police here reliable? I went to see the station earlier and I'm a bit skeptical."

"Those shmucks? You can probably figure out more at my club then if you go to them!" Diamond Tiara huffed. "To be honest, I have no clue what they even do besides scolding people and parading around like they own the place."

Sweetie Belle sighed, "I suspected as much. What about the orphanage? Do you know anything about that? How they treat the kids there?" Sweetie Belle continued.

Diamond Tiara shook her head, "Sorry, not much I can say there. I don't exactly see the caretakers coming around here very often, and nobody other than them that goes in is at the legal drinking age."

"Yeah, I guess not," Sweetie Belle looked down at his list with a furrowed brow. None of these answers were helpful so far. "Moving on - did you know anything about Boris ever having trouble with eating?"

Diamond Tiara gave him a questioning look.

"Like…" There wasn't an easy way to say this, was there? "...Starving himself when Bendy isn't with him?" Sweetie Belle prompted.

"HE WHAT." Diamond Tiara deadpanned.

Well, that answered that question.

"He seems to have trouble being separated from his brother, starving himself and disregarding his health entirely when he is." Sweetie Belle explained as he began to twirl the straw in his fizz wizz around. "It… I wasn't expecting it either."

Diamond Tiara sighed, a hand to her forehead as she leaned against the counter. "Well I can tell you I definitely haven't seen Boris do that." She frowned. "Though they were always a bit on the… thinner side, before they got steady jobs," She grimaced, "But that was both of them, not just Boris. Is this why you came in? To ask about the boys?"

Sweetie Belle was staring at his fizz wizz, twirling the straw with a furrow worried into his brow. He nodded. She hummed. Even Diamond Tiara didn't know anything about it. He was really going to have to ask Bendy when he got back.

Diamond Tiara looked at him, resting her head in her hand. "If that's all you wanted to ask about… I've got a question of my own. If you don't mind."

Sweetie Belle looked up at her, waving at her to go on.

"Why of all days, did you come on Valentine's Day for this?" She gave an amused smile, "When I got the call I half expected something else."

It took a moment for Sweetie Belle to understand what she was talking about. The hearts. The candles at the tables. He sat up ramrod straight. "UH-" It all made sense now. Why hadn't he realized it sooner? Had he really not realized it was Valentines day?

Diamond Tiara laughed. "Calm down there. I'm glad it wasn't about that, if I'm honest. I don't think I'm ready to get back into anything too quickly." She winked. "And I'm glad to know more about the boys, and that you were willing to ask. Even if it's…" Her smile was strained.

Sweetie Belle composed himself and offered her a comforting smile. "Yeah, it's good to know that at least someone in this town cared about them."

There was a comfortable silence. The sound of clinking glasses came from the other end of the counter. Diamond Tiara leaned against the counter. "...And I guess that's why you asked about the station and the orphanage?" Sweetie Belle nodded. "...Well, between you and me?" She shifted her eyes around before looking back to the cat. Sweetie Belle leaned forward. She quickly pecked him on the cheek and pulled away. Sweetie Belle stuttered. Diamond Tiara stood back up. "I need to get back to work," She smiled, waving. "Give that to the boys for me, will you?"

"What-" Sweetie Belle stuttered, feeling his face heat and he pulled his hat down and got out of the seat. "I'll - I'll let them know you said hi!"

Diamond Tiara laughed. "That's not what I said!" Diamond Tiara smiled, "It was nice to meet you, Sweetie Belle! Come back when your next book comes out - I want an autograph!"

Sweetie Belle nodded and waved at her as he hurried to the door.

Diamond Tiara turned, only to spin back on her heel with a shout, "Tell them to stop getting into danger every gosh darn week, too!"

Sweetie Belle's voice was higher than normal, "I will!" And then he was gone.