She didn't sleep that night. When the sun finally rose a few hours later, she slipped into some comfortable clothes, and began walking the six miles from her motel door to the diner.
She pushed open the door a few minutes after they opened. There was an older blonde woman behind the counter, who gave her a polite smile as she walked in. "Take a seat anywhere, honey—I'll be right with you."
Y/N thanked her and took a seat in the booth towards the back, hiding away from the wall of glass that revealed the patrons to the street. The booth's vinyl was a little battered, but still shining brightly in the morning sun. The laminate countertops and checkered linoleum floor were spotless for a moment before the breakfast patrons came in, and everything felt a little unreal because of it.
The woman walked up to her, a tired smile on her face. "Hey darling—what can I get ya?"
Y/N asked for some water, unsure if she'd be able to keep anything more substantial down.
The waitress was gone and back with her water within moments. She then looked over the shaking singer. "You sure I can't get you anything else?"
"I'm, um…I'm waiting for someone."
"…alright. I'll come back later, then."
With that, she was left alone. Y/N didn't take a drink from her glass, merely stared at it as she waited.
This was the right decision, right? If she did this, Dean would be happy. He could see Sam and, when Sam got married, he could go to the wedding, see his nieces and nephews, everything.
As much as Dean tried to play it off, she knew that, deep down, he was a family man, that his family mattered more to him than everything.
So, if she did this, she wouldn't just be able to help him see his brother again, but Agent Singer, too. She still wasn't sure how they knew each other, but she knew how Dean felt about the older man.
Y/N hadn't ever really had a family before Crowley's, as strange as the thought was. She'd been on her own so long that, honestly, it would only be them that would be sad if Crowley did anything to her. And, for the chance to free them all, it was worth it, right?
The bell over the door tingled, but Y/N had hidden herself away in the back of the diner, so she couldn't see who entered.
"Hey Ellen."
"Howdy, Bobby. Been awhile."
"Has a young girl come in here? Y/H/C hair, Y/E/C eyes?"
The woman—Ellen, it seemed—chuckled. "She's a little young for ya, ain't she, Bobby?"
"Nah, it's business."
"Sure a lot-a fellas would love your business, then. She's in the back."
"Thanks. Oh, and, Ellen?"
"I know—never saw either-a ya."
There wasn't an answer, just the sound of heavy foots walking towards Y/N.
Agent Singer didn't say a word as he removed his hat and coat before taking a seat across from her. "You eaten?" he asked.
She shook her head.
He sighed. "Figured. You didn't sleep neither, did ya?"
She shook her head.
He looked annoyed, but didn't press the issue. They sat in silence for a moment before he spoke, "What made you change your mind?"
Y/N gulped. Her throat felt dryer than the Sahara, but she also felt like vomiting, so the water stayed on the tabletop. "I…" she tried, closing her eyes. "Dean missed Easter. He's gonna miss Sammy's birthday, too."
"Balls," He sighed quietly. "You love 'im, don't ya?"
Y/N flushed, but nodded.
"He know?"
"I…I haven't told him yet. How do you tell someone something like that? How do I even know that this is love?"
"Does he know that you're here?" Bobby sighed.
Embarrassment became her primary emotion, and she covered her face. "Oh God."
He chuckled. "I'm gonna guess no."
She shook her head, trying to physically shake off her embarrassment. "No. I thought it best he didn't know just yet."
"Good," Agent Singer nodded.
Ellen came by then, bringing a plate of eggs and bacon for the FBI agent and a muffin for the singer.
Y/N tried to return the muffin, but Ellen just stared her down. "This one's on me, honey. Please, eat something."
The younger woman nodded slightly and held the muffin, taking the smallest bite possible if only to please the older woman. Ellen smiled, thanked her, and walked away.
Agent Singer was practically halfway through his breakfast, scarfing it down like he would never see food again. He looked up at her, putting his knife and fork down, linking his fingers together on the table in front of him. "Well, you know that we could use your help. Obviously. But I need to make sure that you know what you're gettin' yourself into."
She closed her eyes, taking a deep breath. "Will…Will Dean be safe?"
He shifted in his seat. "I can't promise that."
Y/N sighed, letting her head fall into her hands.
"I can't promise that, but I can promise that I'll do everything I can to keep him safe," Bobby's tone made her look back up at him. The determination practically shined in his brown eyes, and she felt a little better.
"All that matters is that Dean is safe. If you can keep him safe, I'll help," she spoke softly, like the words hurt to say.
He nodded.
She looked up at him. "So…what happens now?"
He sighed, leaning back a bit more into the booth. "Well, you can't change anything about your life. Do what you normally do. Can't raise suspicion."
"Okay…" she fiddled some more with her muffin. "What about…what about Dean?"
"Well, obviously, you can't tell him 'bout this."
She sighed heavily, running her hands over her face. "What am I doing?" she mumbled, more to herself than the man sitting across from her.
"Look, if you wanna help Dean, this is the best way to do it. Just…just keep an eye out for anything, any hard evidence you can find around the club. Records, preferably, of how he cleans his money or where he gets it or where it goes. And we can meet here. The Roadhouse is safe, no one'll bother us here."
Y/N rested her head in her hand. "God, how did I end up here?"
Agent Singer's hand closed around hers, causing her Y/E/C eyes to snap up to his deep brown ones. He seemed to struggle for words, the fear that he was losing her and her cooperation practically radiating off of him.
She gave him a soft smile and patted his hand with her free one. "It's fine. Still helpin' ya. Just…two years ago, I was homeless and no one cared. Now…life is strange," she shrugged.
He relaxed a bit at that, letting her hand go. With that, she picked up her bag and began getting up. He frowned, pointing out that she didn't eat.
She answered with a humorless laugh. "I'm still a little sick, I guess. I need to get back to my hotel if I wanna hope to get any sleep before the show tonight."
He nodded. "Okay. I'll meet you here in a week, alright? And don't call me from your hotel room again—use a payphone far from your hotel, Dean's place, the club, anywhere you normally go."
She gripped her bag a little bit more, her knuckles turning white. She gave a curt nod and turned to leave. She thanked Ellen as she walked out, and began the trek back to her hotel room.