Obito had sent one of his associates to send a letter to someone from Detroit, Olivia. The meeting was definitely not organized in anyway but he wasn't very organized nowadays, at least not with everything happening at once; Edward helped him up from his sluggish slumber by giving him a large tug and landing a cup of coffee on the table. He had gotten himself dressed in his symbolized coat that had a cloud on the back and the front and was able to cover at least the lower half of the face but had it unzipped for the time being as he slid into his chair and chugged down the coffee cup, was it odd? 

Yeah. Because he was up late last night. He zipped the coat up and strapped the mask around his face and made his way out, the messenger he sent was already in Detroit and made his way to The Hired Muscle's headquarters and carried the letter in his right hand, the messenger being greeted with simple nod to acknowledge his presence made his way up a staircase and slid the letter under Olivia's office door and then made his way out, making himself inconspicuous as he left the Headquarters afterwards without leaving a word.

Under curiosity, Olivia had seen the letter get slipped under her door and she stood up with a confused look on her face, reaching over to pick up the letter she flipped it open and took out the folded paper inside, the envelope was placed on the desk while the note read:

Hello,

This letter being sent to you is not being sent in error, I think we should meet since I feel that we could be good friends and could be exponential allies in the near future. Brooklyn, New York at Jimmy's Bar at eight? I'll be waiting and that is if you decide to show up, if you need a hint on who to find. Look for a red cloud, don't worry, it'll be obvious so you're not looking around being oblivious.

Until we meet.

~O

The signature letter was written in a cursive dash, pride upon showing off handwriting skills; the letter was written out pretty nicely so it was something to look forward to; Obito made his way out with a small protection detail and made his around town to do errands, the meeting wasn't until later tonight and that gave him the opportunity to complete jobs as he went around to collect local taxes from his fellow associates and kick-ups from previous jobs. A small group of jumpy wise guys cleared their behavior after seeing Obito walk out the front door of his headquarters.

"Afternoon, boss! How-" Obito raised a palm.

"Save it." He said, as he continued walking down the street with Edward right behind him, a smirk ran along his face as the group laughed at Joey who seemed to be the jumpy teenager that had an annoying voice; the laughs weren't any better however, later shoving one another into Headquarters, cars were parked right outside and Edward made a quick jog over to the car to open the door for Obito as he was given a nod as a result as per sliding into the vehicle and getting himself sorted. The door closed and Edward took the driver seat's position along with being accompanied by Alessandro and Luca, he didn't trust himself to be around people he didn't know; gave him a stiff.

The car stopped at a local general store and Alessandro stepped out from the passenger seat and made entry into the store, the trio staring through the window and watching the two discuss; the owner was friendly and knew when they came to a stop with such a group meant collection, sliding wads of cash over to Alessandro as they exchanged handshakes and little did you know; the shop was booming as always with customers coming in and out, the wads made themselves into Obito's possession as he flicked his thumb through the stack of cash, a smile was slapped across his face in accomplishment.

"Christ. I need more coffee, make a stop by that one bakery, will you? Get me a sandwich to go while you're at it." 

"Course, boss."

Making their way to the local bakery, Edward came in and left a few minutes after; he had skipped the line due to his position and while some people made a fuss, the lady behind the counter knew what was up. The coffee was prepared and the sandwich was already in a bag as the lady gave him a gentle smile and wave as Edward exited, Alessandro reached over and knocked the door open so he wouldn't have a struggle outside and gave the bag and the coffee over to Obito with hands reaching out and setting them down in the seat in a position so they wouldn't tip, hands being reached over to his mask to be slid off for the time being as he slouched in the backseat. 

It was gonna be a busy afternoon, and errands were nothing but on schedule for the rest of the day, until tonight that is.

Olivia was in her office that day doing paperwork and looking over the family books. There were a few little shops that were behind in pay their dues and that was simply unacceptable. She pulled a little notebook from her desk drawer and wrote down the names and addresses of the ones that were late in paying; she would visit those personally to speak with their owners and make sure they understood the…urgency…of paying their fair shares.

Just as she was finishing up the daily grind, a letter was slipped under her door. It was odd, no knock, just a letter. Standing, she moved to the door and picked up the letter, pulling open the envelope and reading the message. It was a rather mysterious invitation to the city of New York, to meet who she could only assume to be the newest Crew Leader in Brooklyn. Unless someone else had a name starting with O?

Olivia took the letter into the offices of her crew leader, Ramone. The invitation was a strange one and she wondered why it had been extended to her directly. After discussing it with both him and Ash for a few moments, it was decided that Oliva should go. Granted, it left her very little time to actually get there. Luckily, she kept an overnight bag in the headquarters, so she grabbed that and headed out to the airport, bringing along with her a small number of her personal bodyguards. She couldn’t be sure what kind of situation she was walking into so more of her men would undoubtedly catch the next flight, to get out to New York just in case she needed extra support.

She arrived in New York with a little time to spare. She found a local hotel to check into and squeezed in a hot shower before changing into something a bit more appropriate. She wasn’t sure what kind of place Jimmy’s Bar was, so she picked a versatile outfit of fitted black slacks, a long sleeve grey button up blouse and a black leather jacket. Her dirty blonde hair was loose and fell around her shoulders in waves. On her feet were black pumps that added at least three inches to her already tall frame; a gun was tucked into her belt and hidden by her jacket.

It was just a few minutes before eight when Olivia found the bar that Obito had named in his invitation. She remembered that the letter had said to look for a red cloud, so when she entered the bar she glanced around the room to try and find what it was that was referring to. Surely it would be something obvious, the letter said she wouldn't have trouble.

Obito was done running errands and it was almost time for the meeting, probably running through ten cups of coffee through the afternoon and the morning combined; he was quite energized, the urge to pop a couple fireworks off at Insomnia's place sounded like a good idea but when business calls, business calls and he didn't wanna disappoint not showing up to one of his own meetings and obviously putting off a good first impression helps in the long route.

Obito reached over to take over a book from Edward and was given a pen, he clicked it and began drawing a cloud on the page, every other page was filled with notes but he was bored as he had to make his way over to the bar which was given; the drawing was gonna be a cloud and his drawing skills were somewhat decent after outlines were being scratched into the drawing in general, the cloud almost looked like a painting except without using actual paint with a somewhat blank background with a mask in the back. 

Edward had driven themselves to the bar relatively early, if you consider an hour early; his protection detail was scattered around the bar of course but was mostly arranged out in the booth far in the back of course taking the window seat, raising his arms for them to rest on the seat behind him to make himself stand out, nobody really minded the mask or the coat he was wearing; Obito's own reputation proceeds him and wouldn't dare to talk, if anything, it was expected as a common fashion. 

"Make sure you guys guide her when she gets here. You'll know when she has to look around." Obito exclaimed, so he sat there and waited and looked out the window.

When Olivia had arrived, the place was slightly busy and there were guards stationed anywhere which was expected when you meet with a crew leader; Obito looked at the woman who just entered in and with her being right on time, she was looking around to spot what Obito explained in the letter, a red cloud. The red cloud that symbolized his coat, it was clear on where you needed to go but of course, a bodyguard stepped out of his way and pointed in Obito's direction.

"Boss is sitting over there in the booth, by the window. He's been expecting you." 

Provided after some guidance, the bodyguard stepped back into his position and put his hands behind his back, Obito kept the same resting position he had for an a few minutes; he stared out the window as the night sky glistened into his eye, it was weird; just arranging a meeting out of the blue who knows what you could gain from meeting someone new.

It was a bit awkward, standing there looking around the restaurant. She realized pretty quickly where she needed to go, just as he said she would – after all, the prominent red coat in the back corner was hard to miss. Not to mention he was surrounded by some rather tough looking men, men that looked just like her own bodyguards. Olivia had told her protection to wait outside, which made them very unhappy. Perhaps it was silly of her but Olivia felt it was the best way to establish a relationship of trust. Her men would be on the outside so if something were to happen to her inside well – she might not make it out but it wouldn’t go without retaliation.

Her thoughts were interrupted when a man stepped in her direction, causing her to glance up from the man in the coat to the bodyguard that was addressing her. He motioned over and told her that his boss was expecting her. Of course he was, he’d invited her hadn’t he? Still, she didn’t say that out loud, it was rather rude after all. Instead, she quietly thanked him and headed back to the booth.

She strode confidently to the back, although she made sure to keep her hands visible so as not to seem like a threat to the men who were sworn to protect their boss. She stopped as she got close to the table, waiting to see if the man would turn towards her. Either way, she would speak, her voice soft.

“Hello there. I believe you sent for me?” Or invited, really, same difference. She stayed standing near the table, figuring it would be better for him to invite her to sit rather than for her to be presumptuous. Sure, Olivia could be rather cocky at times, but usually only around people she knew well and who knew her well enough.  

Obito watched as men stood outside, never being in doubt that this was the protection detail for Olivia and they were having a short chat and waving their arms around like if they were in disagreement, the pro of being a masked man is you can show your emotion freely without having someone study you by your facial expression but they could still study you based off your body language but that never hurt anyone; more or less caused issues and furthered trust, conversations take a turn, they always do. 

He turned to watch one of his men step out of line to finally guide the girl over, though it was obvious that he had invited her over in the first place but I guess being a guide also never hurt anyone; when she finally came up her voice was soft and delicate, would make anyone fall in a blissful sleep as a good thing, he looked over and guided his arm to show off the seat in front of him. 

"Hello there. I believe you sent for me?" And she was very much so right.

"Take a seat." 

Obito had stated, he wasn't showing much sass tonight but when does he ever? He adjusted himself in his seat and lowered his arm to rest in his lap while he snapped his fingers and that gave one of his bodyguards enough signal to go get them drinks from the bartender, of course, the deal with the bartender was pre-arranged and as soon as the guy came over he knew what they wanted. He served out drinks on a plate and put the glasses out on the table, each to their own; as they would say.

"My name is Obito." He spoke his own name out with a little of seriousness, was it just to show off? Who knows.

"I invited you, well, just to get to know you; I hope you received my invitation? Joey, my messenger. I hope he did you a service and not a disservice; otherwise that means I'd have to go slap him later." Nothing was holding him back that time, the man standing next to him gulped.

"And you are?"

“Olivia. Olivia Grey.” He had invited her but didn’t know who she was? Olivia found that a bit strange. Or maybe he was simply looking for her to confirm her identity. She took a seat when he told her too, sliding into the booth across from him. Moments after she’d been seated a man brought them drinks. She was surprised to see the bartender seemed to know her drink of choice, a whiskey, neat. Impressive.

He introduced himself, his voice showing a hint of seriousness, and then spoke about his invitation. “I didn’t meet the messenger,” she responded, before sipping from her glass. The liquid burned as it went down her throat, a feeling that was more pleasant then uncomfortable. Alcohol had a way of bringing you to the present, reminding you to stay in the moment. Of course, too much of it could have the very opposite effect. “He slid the invitation under my door. It was rather surprising, I can’t say I expected to be invited to New York anytime soon.”

She leaned forward, her forearms resting on the table, her fingers curled around her glass. She wasn’t nervous, but she was curious and she didn’t really like to beat around the bush. “It does make me wonder why. Why send me an invitation inviting me out here when we’ve never met before?” Surely there were far more important people he could have invited out, like Don Serana herself.

His fingers twirled around the top of the cup and ran his finger across the edging when she asked the question; "Why send me an invitation inviting me out here when we've never met before?" Obito adjusted his posture moments after the question was asked, rather than attend to the rest of everything that was said in conversation, his eyes glared past her shoulder to stare at a man walking in that looks like he was gonna cause trouble but that was just his natural instinct coming into play and he couldn't wrap the feeling around his gut just yet.

"Call me an explorer. I like to meet different people, regardless where they come from. Yeah, it's odd but I suppose it's better than to keeping to yourself by not bothering yourself with other people, just keeping it strictly business all the time. That's boring and I like to do things differently than other people; you could say that. You can't really blame me though, can you?" Obito unstrapped the mask that was covering his face from the moment he walked in and set it beside him on the table. His dark hair really glistened in the light, he ran a hand through his hair and snapped fingers at the bodyguard standing next to him.

Obito leaned in and whispered; "Make sure to take care of Joey later on, bring a couple boys with you. He knows what was gonna happen for not expressing his manners properly." The man nodded and went back to his position, Obito looked back over to Olivia and frowned; "Sorry about the messenger. I'll have to handle him later, but enough of the whole punishment thing, you should really take the time while you're in town to check out the view near the port. The ocean during the day is great but the ocean at night when the moonlight reflects off the water is something else." Obito gripped the cup and took a sip of his drink.

“Explorer Obito?” Olivia grinned, her voice teasing him slightly with the title. “It’s rather bold of you if I might say, to invite random strangers to dine with you, but I suppose a man in your position has the freedom to do just that without too much fear.” She took a sip of her drink and glanced around the room, at all the security he had present and the obvious nervousness of the restaurant staff at serving such an esteemed guest.

She watched as he whispered to one of his men about taking care of some business. She hoped she hadn’t gotten the messenger in trouble by mentioning how he’d slipped the invitation under her door; it’s true it had been a bit odd, but she really didn’t mind all that much. Still, it wasn’t her place to question his decision, so she stayed quiet on the subject and waited until his attention was returned to her.

“I will admit, I have been in New York many times but haven’t really taken the opportunity to explore the city much. Usually, I just fly in, handle my business and fly out the same day.  Who knows, maybe I’ll even find my way there tonight. I wasn’t quite sure what I was flying here for so I left my return date open-ended.”

"Well. What can I say?" Obito shrugged slightly as he reached to take another sip of his drink, the alcohol drowning itself right it into his system was a good feeling, at least for the night; better a good feeling than a negative one, god forbid that it was something else on his mind when it comes to possible assassination attempts or having to get into another shootout, but somehow he was a star at that. The face on the bartender was disgusted as the drunkard was prancing around giving out his quote on quote, best yodel, but it was nothing but bad singing.

He let out a belly-aching laugh before falling on the floor. A grin slapped across Obito's face as he turned back to Olivia as he fiddled around his ring, he adjusted his posture to seem more forward as she talked about being in New York many times but never being given the opportunity to explore the city much. "Well, while you're here. Maybe I can take you out to show you the town, give or take I've already invited you here, inviting someone random. A challenge always runs in my agenda, you decide." He let out a gentle smile.