A/N: The idea for this story popped into my mind and ended up taking on a life of its own. This will be a Dawseride centric story with some Brettsey thrown in occasionally.

Kelly sat at the bar, his shoulders slumped, and waited for the bartender to refill his glass. This bar in the lobby of some random hotel in New York was the last place he wanted to be right now, but here he was. He sighed as he thought about the events of the past 24 hours.

Yesterday he'd flown into JFK airport in New York to surprise Stella. He'd told everyone at the firehouse that it was so that she didn't have to spend her birthday alone, but the real reason for his trip to New York was to figure out what the hell was going on with his fiancée.

He'd barely heard from Stella since she'd left Chicago for her Girls On Fire project. She barely took any of his calls and hadn't initiated a phone call or text with him in over two months. On the rare occasion that they did talk, she always seemed distracted and rushed to get off the phone. He'd tried to be patient and understanding and had initially shrugged it off to her being busy and under a lot of stress, but as the weeks and months continued to pass by and Stella grew more and more distant and showed no signs on returning to Chicago, he'd grown more concerned.

Kelly had texted her when his plane landed, asking her what hotel she was staying at and what her room number was under the guise of wanting to send her a birthday gift. Five hours later, he'd received no response and had taken to calling various hotels around the city asking if there was a Stella Kidd staying there. Two more hours passed before he'd finally decided to grab a room at a random hotel for the night while he continued calling around. He'd given up hope for a reply from Stella at this point and was simply hoping he'd get lucky and find the one hotel out of the hundreds in the city that would be able to tell him that yes, Stella Kidd was a guest there.

After checking in, he'd gone to the lobby bar for a drink and some food before continuing to call more hotels until it got to be too late for him to call anywhere without giving off creepy stalker vibes. He'd crashed for the night, promising himself that he wouldn't give up until he found her.

When he'd woken up this morning, there was a text on his phone from Stella, giving him the hotel name and room number, but saying nothing else. He'd immediately gotten dressed and had begun packing before thinking better of it. If things didn't go well with Stella, it would be better to be staying at a different hotel than her. He didn't want to think like that, but given the way things had been going, he couldn't help but have his reservations about how his surprise visit would go over.

After grabbing a quick breakfast, Kelly had headed to Stella's hotel and taken the elevator to the 14th floor. He walked down the hall to room 1430 and took a deep breath before knocking on the door. He waited for a few minutes before knocking again.

"Excuse me; can I help you?" a hotel housekeeper who had come out of a room a couple of doors down began walking towards him, a wary look on her face.

Kelly flashed her his trademark Severide smile, "Hey; sorry if I'm making too much noise. This is my fiancée's room; I flew into town to surprise her for her birthday," he explained.

The housekeeper looked at him appraisingly before smiling at him sympathetically. "She leaves early every morning and doesn't get back until the evening," she informed him.

"Is there any way I could wait for her in her room?" Kelly asked hopefully, knowing it was a long shot.

The housekeeper shook her head. "I'm sorry, sir; we're not allowed to let anyone into a guest's room that's not listed on the reservation."

Kelly nodded, understanding the reasoning behind the policy, but disappointed none the less. "Thank you for your help," he told her. "I'll come back later."

Around 6pm, Kelly headed back to Stella's hotel, hoping that she had either already returned or would be back soon. He once again took the elevator up to the fourteenth floor, once again walked down the hall to room 1430, and once again knocked on the door. Once again, there was no answer, so he took a seat on the floor, leaning against the door, determined to wait there until Stella returned, no matter how long it took.

Kelly was jerked from his thoughts by someone touching his arm and sliding onto the barstool next to him. He glanced over, opening his mouth to snap at whoever had touched him that he'd prefer to be left alone, but quickly closed it again when he saw who it was.

"You look like shit, Kelly Severide," Gabriella Dawson told him gently. "Now, want to tell me what you're doing in New York, and why you look like you just lost your best friend?

Kelly just sat there and stared at Gabby, still trying to process the fact that she was here. Last he'd heard from her, she was still working in Puerto Rico, helping with the recovery from Hurricane Maria and the earthquake. Yet, here she was, dressed in a navy evening gown, sitting next to him at a bar in a hotel in the middle of New York City. He blinked a couple times trying to make sure he wasn't so drunk that he was seeing things.

"Kelly?" Gabby asked softly, her brow furrowed in concern.

Kelly shook his head. "Sorry; I was just surprised to see you here."

"I could say the same about you," Gabby replied, bumping his shoulder gently with her own. "New York is a long way from Chicago."

Kelly sighed and ran his hand through his hair. He quickly downed the drink the bartender had set in front of him when he'd been lost in his thoughts and signaled for another one. "Want anything?" he asked Gabby as the bartender made his way over.

"I'll take a gin and tonic," Gabby told the bartender, who nodded and quickly got to work getting their drinks. She then turned to Kelly. "Now, will you please tell me what you're doing in New York?" she asked.

Kelly accepted his drink from the bartender and then turned back towards Gabby. "I came to see Stella," he muttered.

Gabby looked at him in confusion. "What is Stella doing in New York?" She looked around before adding, "And if you came to see Stella, where is she, and why are you sitting here drinking alone? Did something happen?"

"It's a long story," Kelly sighed, taking another swig of his whiskey. "It starts with me being stupid enough to think that Stella actually loved me and that my luck with women had finally changed and ends with her giving me her engagement ring back."

"Oh, Kelly," Gabby sighed, her heart hurting for her friend. One she'd decided to stay in Puerto Rico, she'd lost touch with the majority of her Firehouse 51 family, only hearing from them occasionally when something major happened, like Otis's death and Cruz's wedding. She'd received a call from the happy couple when they'd gotten engaged, but she'd obviously missed out hearing anything that would help her fit together the puzzle pieces of why Stella was in New York in the first place, and why she and Kelly had broken up.

She quickly downed her gin and tonic before signaling to the bartender for another. She knew she'd need more alcohol in her system before she heard the rest of this story.