Disclaimer: I do not own "Supernatural"

Summary: Jess has a few questions about Dean.


"God, this paper is killing me. I can't believe how impossible it is to get current, reliable sources. NOBODY fact-checks anymore! It's ridiculous!" Sam grumbled as he dropped down on the sofa next to Jess.

She was curled up on the cushions, her feet tucked beneath her. She'd been reading a paperback a few hours ago when he'd retreated to the study. Sam searched for it and found it face-down on the coffee table. "No good?" he asked, motioning towards the book.

She smirked a little. "It's fine. Perfect brain-candy." The words were soft, though, and she didn't meet his gaze.

"So what's up? You usually jump right in on my the-deterioration-of-the-U.S.-academia spiel -"

"Just got off the phone with Jilly."

Sam felt his mouth go dry. "Oh, boy. What now?" he asked, wryly. "Is the shade of my brown hair still too non-descript for her?"

Jess offered him a small smile. "She called to say she was wrong."

"What! Seriously?" he squeaked. "And you didn't put her on speaker phone?"

"She wants to come meet Dean. She said that she's thrilled I've gotten to know your brother."

Sam blinked in surprise. It hadn't occurred to him that Jess would talk to Jill about Dean. He swallowed hard suddenly. "Um, well . . . he's not gonna – he said he was goin' to Georgia, remember?" he murmured, quickly running through his mind all the blackmail material he'd have to use to get Dean to come have dinner with Jess's sister.

"Yeah. Georgia . . . on a job."

His thoughts halted abruptly. It was the way she said those three words, on a job, that alerted him to the level of wrongness here. It was high, past orange . . . maybe red.

"I told Jill I didn't think it was a good idea," she continued. "Jill insisted, and we got into an argument."

Sam's eyes widened a little. It wasn't unusual for Jess to get into an argument with her sister. It was unusual for it not to be resolved in the same phone call, though.

"It's kinda ironic," she continued after a moment, and Sam's hands started sweating. "She calls to tell me I have no business marrying you when I don't know anything about you -"

His eyes widened at that; where the hell did Jill get off? Sam opened his mouth, but Jess continued without giving him a chance to speak.

"- and I tell her to go to hell and list all the reasons I do have to marry you. I tell her all the things I do know about you. How wonderful you are and how smart and determined; how happy you make me, how safe you make me feel."

His mouth closed and he smiled at her a little; she didn't smile back.

"But when she calls to tell that she was wrong, that maybe you aren't harboring a secret life of crime, and that she's so happy I'm getting to know your brother. When she calls to say that she wants us all to get together . . . I have nothing to say."

Jess sounded so sad and lost that Sam's heart thudded. He took a deep breath and reached out to take her hand. He squeezed her fingers a little. "Help me out here, baby, 'cause I'm lost . . . what's wrong?"

She gazed at him for a moment and Sam's heart beat faster. What was going on here? What had Jill said? Why was Jess so quiet?

"Am I really?" she asked after a moment, and Sam was so relieved that she spoke, it took him a moment to register the weariness in her tone.

Sam swallowed hard. "Are you really what?" he asked softly.

"Am I really getting to know your brother?"

His breath left him in a rush and he pulled his hand back from hers as if he'd been burned. "What?" The word left his lips on a gasp and the meter on the level of wrongness blew past red and off the charts.

Oh god.

He should have known.

Christ, in a way, he had known.

It had been a fantastic summer; more than that even. It had been ideal. An unexpected gift bestowed on him by an unknown deity – fate, God maybe . . . it didn't matter. All he knew was that for one amazing summer he'd had the best of both worlds with no strings; no questions asked, no explanations necessary.

Maybe it had been the high of graduation and the upcoming wedding, the high of new jobs and new phases of relationships; but Jess, his friends too, had been so easy with Dean. Nothing but laughter and teasing, questions about childhood pranks and punishments – nothing serious, nothing that couldn't be evaded with a hilarious anecdote.

He'd seen it coming though . . . the end. Far off at first, but it had been speeding closer lately.

The glamour of the summer was fading, and he'd seen Jess's questions.

He should have known this was coming.

The way Jess stared at him when he announced that Dean was in the area. The look in her eyes when Dean left; the way she watched the efficient way he packed and unpacked. The way she studied the faded scars on his chest and legs, and Sam knew she was mentally comparing them to the ones on his own body. The way she eyed them both after they spent a few hours in his study alone – questions, so many questions.

But she'd held her tongue. Sam didn't know why, but she had.

Until now.

He'd known this was coming – you'd think he would have been prepared . . .

Jess shrugged a little. "Am I really?" she asked again.

"You... you know Dean," Sam answered softly, swallowing hard. It was true, maybe not completely, but she did know him. "You do," he added for emphasis.

It garnered a small smile from her. "I think I do . . . I hope I do," she murmured.

"Jess -"

"I like Dean," she cut him off. "I want to make that clear, before I say what I want to say in this conversation."

Sam flinched. He knew that tone. It was her I'm-putting-into-practice-a-technique-I-read-in-my-psych-book tone. He opened his mouth, but Jess put her hand up, cutting him off quickly.

"He's definitely on my top 10 favorite people list."

The made him smirk. Jess's list was a long running joke, "I'll be sure to let him know," he murmured.

Jess shot him a quick glare and he wiped the smirk off his face. "Listen, Jess -"

"I'm not sure I actually know him though," she said in a rush. Her eyes dropped from his face; she was uncomfortable with this conversation, he realized.

Well, good. They were even.

He knew what was coming next; had known all summer that it would come eventually. Sam opened his mouth, knowing it was futile to try and head it off, but having to try anyway. "You know him -"

"Where does he live? Why does he travel so much? What are those jobs you two are always talking about? What does he do?" she asked, again in a rush, but this time looking up at him, eyes earnest and almost pleading. She wanted to be let in. He saw that, knew that . . . and knew that he would never do such a thing to her . . .

What does he do?

The words echoed in his mind. What did Dean do?

Christ.

How was he supposed to put that into words?

Dean dug up bodies and buried corpses...

"Sam?" Jess murmured, and he blinked at her. She sighed roughly, dropping her legs from the sofa onto the floor. "This is exactly what I mean. How can I actually know him if I don't know stuff like this? I mean okay, I know what he's like. I know he's fun and a great guy and whatever, but my sister is gonna want to know more than that. This is basic stuff, stuff I should know about my brother-in-law..."

Dean stole identities and impersonated officers of the law...

"I haven't asked all summer because somehow I knew it would be an issue, and I didn't want to bring up any issues because you were so happy he was here. And I love having him stop by and I love how happy you've been and I love watching you two together . . . but Jilly is going to ask questions, and she isn't going to take silence like this."

Dean hunted monsters, banished spirits, killed things...

"You know how she is. She's going to insist and Dean's going balk because that's how he is, and everything's going to be a mess. That's why I told her she could meet Dean at the wedding, because I figure at the wedding they're both going to be on their best behavior; but then I remembered the rehearsal dinner and now I'm just, sorta, kinda freakin' out a little bit..."

"Jess."

He said her name quietly, firmly, and she immediately stopped talking and turned to look at him. Her blue eyes were a bit frantic and he wanted to kiss her, because he knew how worked up she'd been about this. How long she'd made herself hold back the questions, because she didn't want to upset anything.

What does he do?

The question echoed one more time, before Sam answered it. "He saves people."

Jess blinked at him for a moment without saying anything, then she frowned a little. "He saves people?" she asked softly.

Sam nodded, already feeling a little sheepish, "Yeah."

She nodded and took a deep, shuddering breath, then tilted her head a little to one side, studying him. "How? I mean, he's not a cop," she stated after a moment, managing to sound certain and questioning in the same breath.

Sam's eyes widened and he shook his head quickly, "No, no . . . not like that."

"Or a fireman? Or a paramedic . . . all those things wouldn't require all this moving . . ." she added quickly. Sam knew then that she might not have asked all summer, but she'd been thinking on it – a lot.

Sam shook his head again. "No, he just . . . he helps people," he said and she remained silent.

Jess was waiting, and after a moment he continued slowly, "People that . . . the, uh – police . . . can't help . . ."

Sam could have kicked himself when her eyes narrowed. God, he was screwing this up.

She nodded slowly, but there was still confusion written all over her face. "Why? What's wrong, that the police can't help?"

Cops don't load their guns with rock salt and regular clips don't work on poltergeists.

Yeah. That would go over well.

He took a deep breath, dropping his eyes. "Sometimes the police just . . . can't; they don't know how – or they . . . just . . . they can't," he stuttered out.

Well, it was true.

Her face cleared suddenly. "Because of . . ." she paused, ". . . the laws, right?"

Sam started a little, "What?" He shook his head quickly. "I never said anything about laws -"

"He's got the sharpest, most deadly-looking knife I've ever seen in that duffel bag," she interrupted. And Jess sounded much too carefree about it for Sam's comfort – like she'd been contemplating the fact that his brother lived a life of crime.

"How do you -"

"I snuck a picture in there a while back and found it."

Sam's eyebrows shot up. "That's all you found, right?" he asked, before he could stop himself. He'd asked Dean not to bring a gun into the apartment.

Jess frowned. "Was there supposed to be something else?"

He blinked. "No, no . . . I just . . . you can never really be sure, Dean, he -" Sam cut himself off abruptly then added more firmly, "No. Of course not. Nothing else."

They were silent a moment, then Jess asked softly, "So, he helps people that . . . the police can't . . . how?" It was soft and hesitant and Sam wanted to scream, because he should have been prepared for this, because he couldn't blame her for asking, because he had no idea what to say –

He looked down, away from her, and a moment later he heard her sigh.

"Is it illegal? Is that why you don't want to tell me?" she asked.

His head shot up; again she sounded way to blasé about this for his liking. "No." He said it firmly, although technically, yes, most of what Dean did – what Dad did, what he'd done – was illegal.

"Dean's a good guy. He has a good heart, like you. But he's . . . rough around the edges a little bit. So I've sort of resigned myself to the fact that his chosen profession may or may not be legal . . ."

Sam gaped at her; he couldn't help it.

Jess shrugged. "It's not like I woke up this morning and thought, hey! I wonder what Dean does! It's been on my mind for a while."

"He's not – he doesn't -" Christ, what was he supposed to say? Jess was on the right track, and he had to get her off it. It wasn't legal, what Dean did, but he couldn't let her think that.

Eventually, letting her think that would come back to bite him in the ass.

"It's not illegal," he lied. "It's . . . he finds things for people," Sam muttered.

"Like a P.I.?" she asked, inching forward a little suddenly.

A Private Investigator – Christ.

"Well, uh, sort of . . . but more like things – uh, people,I mean, that are . . . hurting other . . . people . . ."

"People that the police can't find?"

"Yeah, I mean . . . it's not exactly . . . their jurisdiction . . ."

"So he catches the bad guy?" Jess asked, eyes suddenly animated. Sam was afraid that he was giving the wrong impression here.

Yeah, Dean did catch the bad guy – but the bad guy was usually dead, sometimes undead.

Slowly, he nodded. "Yeah . . . I guess, but . . . I mean, it's not that – dramatic . . ."

God, don't make it dramatic, please, Sam thought fervently. The less fuss made about Dean's job, the better.

"So he's like a bounty hunter?"

A bounty hunter?

"Um . . ."

A bounty hunter? A supernatural one, maybe...

The thought made him smile suddenly. Dean was a supernatural bounty hunter –that actually kinda fit. Except for the whole not-getting-paid thing.

"Yeah, I guess, something like that -"

Jess nodded, her face beginning to clear. "So . . . where, I mean . . . is there an . . . office for that?"

Sam nearly laughed in her face at that. Dean was not an office kind of guy.

He shook his head. "No, no . . . it's . . ."

"Freelance?" she supplied, inching forward again.

Sam swallowed, nodding – okay, yeah, sure, that was one way of putting it.

"So people pay him to," she paused, "fix problems for them – problems the police can't. And he – catches people and finds things . . . and . . ." her face lit up suddenly. "That's what your Dad does too, isn't it!" she cried. "That's why you moved around a lot. That's the family business that Dean meant," she stated.

When had Dean mentioned the family business?

He nodded slowly. "Uh, yeah . . ."

"So he's part P.I., part bounty hunter, huh?" Jess murmured, smiling. A smile that widened suddenly. "It totally fits him, you know," she gushed.

Sam continued to stare at her.

She seemed happy with this.

"See?" she added, reaching out and patting his arm. "Was that so hard?"

He shook his head. "Jess -"

"I know that for someone like you with all that legal stuff in their head, where everything has to have its little corner, it must be hard that Dean has no job title, but it's okay, really," she comforted. "It's kinda an odd job, but it totally fits Dean perfectly and you have to learn to bend a little," she finished.

He realized that somewhere in her head she'd concluded that he was ashamed of Dean's – and by proxy, his Dad's – job. And that was the explanation for his silence. He hadn't told anyone because he was an uptight, inflexible, legal-minded individual – not because it was illegal.

Huh, go figure.

"I have to call Jilly and tell her," Jess murmured, getting up. But instead of moving away she laughed. "Oh, god, she's totally going hate this!" she giggled.

Sam nodded absentmindedly.

"How long's Dean going to be in Georgia?" Jess asked.

Sam's mind was still racing – a bounty hunter?

Jeez.

Dean was going to kill him.

"Um, a week probably," he muttered.

"Is that how long it usually takes him?" Jess asked, eyes glimmering with interest. "That's not very long. He's good, isn't he?" she added lightly. Sam realized suddenly how much it had bothered her to not know, how much she'd wanted to know.

A bounty hunter.

A Private Investigator.

She didn't know, not really -- and yet . . . a private investigator found things – like Dean. And a bounty hunter was a hunter, so maybe . . . in a way . . . she did know.

Bounty hunter, private investigator – they were . . . translations of what Dean did. Hell, they were close translations.

A smile suddenly stretched across his face.

Why hadn't this occurred to him before? Dean did find things that the police couldn't and he obviously hunted –true, the things he hunted weren't human, and he didn't actually get paid for any of it, but the basics were mostly true and the most basic was absolutely true. Dean helped people.

His smile was so wide that Sam knew he must look like an idiot, but he didn't care. Jess knew what Dean did . . .

"Yeah," he said softly. "He is. He's very good at what he does."

She nodded. "I'm sure he -" Jess scowled suddenly. "You two should just have told me. Do you have any idea how many theories I've come up with?"

Sam chuckled, "No. But I'd love to hear them someday." I know you didn't hit on the right one, babe, he thought wryly.

Jess rolled her eyes. "I'm gonna call Jilly. How 'bout in two weeks for the dinner?"

Sam frowned. "That's kinda early for a rehearsal dinner. Don't we have to plan for -"

"No, not the rehearsal dinner. Just us four for dinner -"

"I thought you said that you didn't want to do that?"

"That was before," Jess corrected. "Now I HAVE to my sister's face when Dean tells her he's a freelance bounty hunter," she laughed again. "Jilly's gonna have a cow!"

Sam snorted. "Jill dyed her hair orange last month; she's not one to talk."

"Ah, but she will, Sam, she will have lots to say," Jess stated, turning to go into the kitchen. "And I can't wait to see Dean listening . . ."

Sam rolled his eyes. He wasn't worried – Dean had been evading questions from people like Jill forever.

The fun part of this little just-us-four dinner was going to be informing Dean that not only was he coming, but convincing his older brother that he was now a freelance bounty hunter and Private Investigator. Oh, yeah.

That was going to be fun.