Dean
"Sam, it's fine," Dean tried to reassure his brother, to no avail.
"It's a girl," Sam hissed, shooting him the dirtiest of looks. "You want to take her on a date, take her to dinner! Don't bring her along on a case. God, Dean, she's not even a hunter."
"How do you know that?" Dean argued, lifting his chin a little with newfound confidence. "Huh? Did you ask her? For all you know, she could have salt and holy water in the trunk of her car."
Sam's face was totally and completely disbelieving, frowning sideways at him. "Dean, I saw her go to her car. All that's in there are books and her cell phone. You think she has weapons in the trunk of her tiny, lime green, VW bug? Does she look like a hunter to you?"
Dean glanced over at the girl—Y/N, according to her nametag—and sighed. Sam was right, she didn't look like anything more than a frazzled waitress with more customers than she could handle by herself. But she didn't just look like a normal girl, either. Here Dean was trying to be undercover, and this total stranger had cast some sort of spell on him. What was he thinking bringing a girl along on a case? Sam was right, he should've just taken her to dinner.
"Let me try and fix this," he muttered, and walked back over to the bar, hands stuffed in his pockets.
She raised her eyebrows at him when he approached. "Back so soon?"
"I can't take you with us," Dean sighed. He avoided meeting her eyes again. That was how he'd fallen under her spell in the first place.
"How come?"
Dean mumbled something about secret PI stuff and Sam not approving. But Y/N would have none of it.
"Unh uh," she said, putting her hands on her hips. Her face was defiant. She was not budging a single inch until he gave in. "You said you'd prove to me that you guys are the real deal. Now's your chance. Are you chickening out 'cause you have something to hide?"
"No," Dean said, probably a little too quickly. "It's just—"
"Just what, exactly?"
Dean's mouth open and closed silently for a few seconds as he struggled to find the right words to say. He finally blurted out, "Do you want to have dinner with me?" Then pressed his lips together before anything more could slip out.
The corners of her mouth twitched, ever so slightly. "Did you just invite me on a second date before even having gone on the first one?"
"What—no!" Dean sputtered nervously. He felt his face heating up, and judging from her triumphant smile, it showed. "No! The investigation is not a date."
"You sure made it sound like one."
Dean attempted a casual, slightly annoyed roll of his eyes, but it didn't feel very convincing, even to him. "How did I make it sound like one?"
"Because real PIs don't invite total strangers out on their investigations."
"I am a real PI!" Dean insisted.
"Okay." Y/N turned her back on him and grabbed a pitcher of icy water, condensation dripping off the bottom. "If you say so. We're still on for seven, right?"
Dean thought Sam was going to hit him when he shuffled back to the booth, eyes on the floor.
"I didn't mean in addition to!" He half-shouted. He rubbed his temples like he had a headache. "You know what, fine. We'll let her see us questioning the police, we'll be using code anyway, and then we'll leave. She'll drive home, then we can do the real stuff."
"Uh, about the driving . . ." Dean trailed off and smiled nervously at Sam, who glared venomously.
