Chapter 24

Jessie glanced uneasily at the door—which Sam and Dean has just walked through—carrying a bucket of chicken and a few paper bags with food. She hadn't realized they'd told Bobby about everything the demon had said, so when he asked her if she was in love with Sam, she'd been completely blindsided. She wasn't quite sure of the answer, even if she wanted to tell him. But worst of all, the brothers had walked in just as he was asking her, and she was positive they were all waiting for a response.

She glanced back at Bobby looking completely uncomfortable. "I don't know, Bobby."

It was about as close to the truth as she was willing to speak out loud, at least while in mixed company.

The brothers placed the bucket and bags of food on the table, then dug out the paper plates. Everyone took a plate, then they passed the food around, each taking whatever it was they wanted.

As hungry as Jessie was, she was finding it difficult to eat and pretend everything was fine and normal. Everyone else seemed to be able to, which infuriated her. She wanted nothing better than to forget all of the awkwardness and relax. But no matter how much she wanted it, it was impossible. Even with alcohol.

After they were finished eating, things became a little more uncomfortable for everyone. Dean had chosen to sit on the couch and watch TV, while Bobby and Sam were bent over his laptop discussing something other than herself or Crowley, which was a relief.

She hadn't noticed when she had first awakened, but it had actually been pretty late in the day. Her sense of time was seriously out of whack, due to her being possessed.

All she wanted was a few moments alone to herself, she needed it. Her time in the shower had been a nice break, but she was feeling like the walls were closing in again. She got up from the table and walked to the door, but Bobby yelled at her before she could open the door fully.

"Where do you think you're going?"

She turned to glance at him irritably. "I need some fresh air, Bobby."

"Alone?"

She rolled her eyes impatiently. "Fine. Dean can come with me."

Everyone looked at her with surprise, though none with as much surprise as Dean.

"I'm not getting any fresh air in here, Dean," she said impatiently.

He jumped up from the couch in a hurry, following her out the door. He had to step quickly to catch up to her.

"Where are we going?" he asked curiously.

She didn't answer him. Instead she kept walking until she reached the motel office, with him right behind.

He continued to watch silently as she paid for another room on her credit card, then walked out of the office, heading to the pop machine. She dug out some change from her pocket, put it in the machine, choosing a cola. As she opened the can, Dean couldn't deal with the silence any longer.

"Why did you choose me to escort you?"

She gazed at him evenly. "I assumed you would be the the least likely to try and strike up an uncomfortable conversation with me." She paused, cracking a slight smile. "Guess I was wrong."

"Oh. I was just surprised."

"Why, Dean?"

"I just figured you wouldn't want me anywhere near you now that you, uh, you know," he stammered.

Her smile disappeared quickly as she realized what he'd meant. "Now that I remember that night you mean?"

"Yeah."

She looked away for a moment, before turning back to him. "I thought we moved past this, Dean. But that bitch stirred it all up again. I know I overreacted when I woke up earlier, but that's all it was. Nothing's changed."

"I'm really sorry, Jessie. I never meant..." he trailed off, unable to finish his thought.

"It's okay, Dean. Really."

A short moment of awkward silence followed, before Dean broached another subject. One he hoped wouldn't seem quite so controversial.

"So who's the other motel room for?"

She smiled. "For you and Sam, of course," she replied as she handed him the key.

He raised an eyebrow in curiosity as he took the key. "You didn't have to pay. It's not like I'm destitute."

"Just take the damn charity and shut up," she replied with a hint of a smile.

He smiled, then followed her as she began to walk back towards her motel room, until she stopped at the doorway and turned to look at him.

"Was there something else you wanted to ask me?"

He shrugged, looking perplexed.

She gazed straight into his eyes, looking serious and determined. "The answer to Bobby's question is, yes. I'm in love with your brother, Dean."

He was taken aback by her directness, but not by her answer.

"Why are you telling me this?"

She chuckled slightly. "I would've thought that was obvious. I wanted you to know before things became too awkward between us."

"I told you I was fine if you wanted to be with Sam. It was the truth."

She opened her mouth to say something, then closed it quickly, rethinking what she had been about to say.

"I don't know what it means, Dean. But I have a feeling that Sam and I could never be happy together."

"Why would you say that?" he asked with surprise.

She snorted in disbelief. "Should I write a list? At the top of a very long list would be demons."

"We'll deal with that, Jessie. You shouldn't worry."

"You make it sound so easy, Dean. But I'm not as optimistic as you are."

He laughed ironically. "Optimism has nothing to do with it. I just know there's always a way to deal with those sons-a-bitches."

"Maybe you're right, Dean. But things never seem to work out the way I expect," she replied with a long sigh.

"You and me both," he agreed. "But that doesn't mean you shouldn't try."

She smiled, shaking her head slightly. "If you can be sympathetic and wise, I guess there's hope for us after all," she teased.

"Yeah, yeah," he said with a grin. "Let's get inside before someone worries we've killed each other."

She laughed. "Thanks, Dean."

"For what?"

"For putting me in a better mood," she replied as she opened the door.

Dean followed her inside the room, then slumped onto the couch turning the TV back on.

Jessie walked over to the table where Sam and Bobby were still bent over Sam's laptop and sat down beside Sam.

"You didn't kill Dean," he said with a grin. "You must be feeling better."

"Don't tell him this but, he actually made me feel better," she replied in a hushed voice.

He smiled at her brightly, making her smile in response.

Bobby reached over the table, dropping a silver charm in front of Jessie, staring at her intently as he did.

"Wear that."

She gazed back at him defiantly. "I don't like wearing jewelry, Bobby."

"You have two choices, young lady," he said commandingly. "You either wear that, or get a tattoo. No arguments."

She continued with her defiant look for a moment longer, then burst out laughing.

"There's no contest, old man. I'd rather get a tattoo than wear that thing," she replied, then pushed the charm in his direction.

"Fine," he replied without missing a beat. "That's on tomorrow's agenda then, Jess."

"Fine," she replied with a shrug of her shoulders that meant she agreed with him.

He scooped the charm up from the table, pocketing it. Glancing back at her, he opened his mouth, then his phone rang, which he answered promptly.

She looked at Sam, trying not to smile so brightly, but only managed to make herself feel foolish.

"I never got to thank you, Sam."

"What did I do?" he asked with surprise.

"If it wasn't for your sympathetic voice, I doubt I'd have moved from that couch."

"Yeah, you would of," he replied modestly.

He reached a hand under the table, taking her hand into his, squeezing it gently, while he was smiling at her.

The touch of his tender grasp sent a wave of warmth through her, making her smile shyly.

Suddenly, Bobby yelled, "Balls!" and slammed his fist on the table, snapping Sam and Jessie out of their tender moment.

"What's wrong?" she asked him, as she quickly pulled her hand from Sam's looking guilty.

"Nothing important," he said dismissively. "Just some fool hunter who's gone and got himself into some trouble."

"What else is new?" she said teasingly.

"Tell me about it."

She didn't know what made her think of it, but she figured it might have something to do with her sudden feeling of shyness. She got up from the table, dug around in her duffelbag, pulling out a deck of cards. After walking back to the table, she flopped them down as she took her seat again.

"Who wants to play poker?"

Dean immediately jumped up from the couch and ran to the table with a wide grin on his face.

"I'm in," he said while staring at her. "I wanna see you put your money where your mouth is."

She laughed at him. "That's right. I did say I would wipe the table with you, didn't I?"

Bobby and Sam exchanged anxious looks as the two of them stared each other down.

"Okay, let's bring this down a few notches," Bobby said glancing back and forth between Dean and Jessie.

Once everyone had settled down and agreed to play, and agreed on rules, and antes and everything else involved. They each threw $100 into a pile, then Dean fetched Jessie's set of poker chips from the trunk of her car.

He asked her why she had them in her car, but she only gave him a dirty look and refused to answer. He figured she played way more poker than she'd let on. But that wasn't going to stop him from taking her down a few pegs. He was positive he could beat her.

It was well into the second hour, when Sam finally lost all of his chips. Jessie and Dean had the biggest pile of chips, but Bobby still had more than enough to be able to catch up. However, it was shortly into the third hour when he lost all of his chips in a large hand, that Dean happened to win.

Jessie and Dean played for more than an hour after Bobby dropped out. He stayed at the table to deal for them, hoping it would end the game quicker, but that didn't happen.

It was almost five hours since they'd begun to play, when the last hand was finally played. The showdown between Jessie and Dean, ended with him winning. He tried really hard not to rub it in, but he couldn't help doing exactly that before he headed to his own room to sleep.

After he was gone, and Bobby was busy, Sam turned to her with a conspiratorial grin on his face.

"You let him win, didn't you?"

"What?" she replied as she packed up the poker chips. "I'd never throw a game of poker, Sam."

He grinned at her as he took the case of chips from her. "You can deny it all you want, but I know what you had in your hand."

"You only think you do, Sam."

"So you didn't have a full house?"

She narrowed her eyes at him. "If you're that good, why were you the first one out?"

"I was enjoying myself more watching you play," he replied with a smile.

She smiled shyly, before looking away. "It's time for bed, Sam. I'll see you in the morning. I mean, whenever it is I wake up."

"Okay. I'll see you later then," he replied, carrying her case of poker chips with him as he left.

She watched him leave, before climbing in to bed and falling fast asleep.

When Jessie finally woke up, it was almost noon. It normally would have upset her getting up that late, if it hadn't been early in the morning by the time she'd manage to get to sleep. She glanced around the room, noticing that Bobby was already awake and on the phone.

"Dean dropped off some breakfast sandwiches earlier," Bobby said pointing to a paper bag on the table as he covered his phone.

"Coffee?"

His eyes widened slightly, mouthing the word, "Sorry."

She sighed in aggravation, grabbed her dufflebag and went into the bathroom to get fully dressed. She could do without food before she could do without coffee.

When she was finished in the bathroom, she put her shoes and jacket on and was about to walk outside, when the door opened and in walked Sam carrying a coffee.

"Please say that's for me?"

He smiled mirthlessly, handing it to her. "Of course."

She smiled thankfully, taking a sip. "Thank you, Sam."

"I would love to tell you it was a noble thing," he said with a teasing grin. "But I was afraid to show up here without coffee for you."

She narrowed her eyes dangerously before raising an eyebrow in a sarcastic manner. "Ha, ha, Sam. You're just as hilarious as your brother."

He laughed as she gave him a pouty look and walked away looking insulted.

She reheated two of the breakfast sandwiches, then sat at the table to eat them. She listened as Bobby was talking animatedly on his phone with who she could only assume was another hunter. When the profanities began to fly, she knew for sure it was another hunter. She figured she probably knew who it was just by the spirit of the conversation. Someone she wasn't very fond of either. In fact, the last time she'd spoke with the same man, she'd said some colorful things as well. Not to mention a promise to kill him if she ever ran into him again.

At some point while she was lost deep in thought, Dean had come into the room and was now arguing with Sam about something. She had missed some of the argument, but she was listening now.

"I told you no, Dean," Sam said firmly.

"Why not? What's the worst thing that could happen?"

"Are you being serious right now? Or have you finally lost your mind?"

"I'm being serious, Sam. You wanna know what's going on just as much as I do."

He snorted. "We can't trust him anymore, even if he did want to help us."

"He was like family once. Why can't we at least try?"

Suddenly, Bobby's voice boomed louder than the Winchesters' argument.

"What the hell are you two idjits arguing about?"

Dean and Sam both turned to gaze at him simultaneously, looking guilty.

"Well?" Bobby asked impatiently.

Jessie couldn't help but giggle quietly at the absurdity of the situation.

"It's nothing, Bobby," Sam replied dismissively.

"So you were fighting for nothing?" he asked with irritation glancing at Sam, then Dean.

Dean shot his brother a tenative look, before turning back to Bobby. "I just had a suggestion on where to look for help, but Sam doesn't think it's a good idea."

Sam glared at his brother looking deadly.

"Spit it out," Bobby demanded.

She didn't know why, but Jessie felt like she didn't want to hear his suggestion. Something in the way Sam was looking at his brother almost frightened her.

"I thought maybe we could try to contact Cas."

Before anyone could reply, Jessie stood up and yelled. "Absolutely not!"

The three men turned to glance at her in surprise.

"Why would you have a problem with it?" Dean asked indignantly.

"This is my life we're talking about, Dean," she replied furiously. "I don't want angels involved."

"You don't even know him."

"I don't want to know him, Dean," she said angrily. "You seem to forget all the lying and manipulating he did to you and your brother."

"A lot of things have happened since then. I'd like to think people can change."

"People!" she snorted. "He's an angel. They can't be trusted any more than demons can."

"I don't think that's a fair statement."

"I got one word for you, Dean—apocalypse."

"Jessie," Bobby called her, cutting off Dean from saying anything else. "I think maybe we should consider this."

"What?" Jessie and Sam exclaimed simultaneously.

"Have you gone insane, old man?" she asked before he had a chance to say anything else.

"No, Jess," he replied seriously. "I'm not very fond of angels either. But at the same time, we need to know what's going on."

"We don't need to know this badly, Bobby."

She glanced over at Sam, who returned her look almost apologetically. He seemed just as uncomfortable as she did. She sorta waved her hand, suggesting he come sit at the table with her. She could only hope he understood what she wanted.

He walked over to the table and sat beside her, glancing at her with trepidation.

"I'm sorry," Sam said in hushed tones while Bobby and Dean were having a conversation between themselves. "I don't want this to happen either."

"I don't understand why Bobby would even go along with this. He was never terribly fond of Castiel, and that was before he betrayed everyone," she remarked quietly.

He reached his hand out, grasping hers tightly. "I think he's just afraid, Jessie. I think he's so afraid something will happen to you that he's willing to do whatever it takes."

She glanced down at her hand, which Sam was still holding tightly, then raised her eyes to gaze into his. "What about you?"

He looked uneasy for a few moments as he tried to figure out what she was asking.

"I'll do whatever it takes to keep you safe, Jessie. I just think Cas might make things worse."

She squeezed his hand tightly. "In case this all goes wrong, Sam. I want you to know something."

He shook his head, smiling brightly. "You don't have to tell me, Jessie. I already know."

"Your brother said something, didn't he?" she asked, narrowing her eyes suspiciously.

"No, it wasn't him, and it wasn't that demon," he said, smiling mirthlessly. "It was you."

"What? When?" she asked with confusion.

He smiled, chuckling lightly. "You can be so cute sometimes."

She gave him a look that said she was clearly not amused.

He smiled. "You don't have to say the words. I know how you feel."

"And how is that exactly?"

"Your eyes give you away."

She felt her breath catch in her throat, then turned away as she felt heat rising to her face. She didn't want him to see her blush. She already felt vulnerable enough.

When she was ready to face him again, she turned just in time to hear Dean calling for Castiel. She jerked around, then stood up looking furious. She thought she would have lunged right at him, if Sam hadn't had a tight grip on her hand.

He stood up directly behind her, wrapping one hand around her back, holding her by the waist, while he held her other hand tightly, entwining his fingers with hers.

In normal circumstances, she might have felt awkward about him holding her the way he was. But at the moment she didn't care. She needed his support more than she cared about how it looked.

She stood silent as Dean was calling out for the angel, Castiel. But her facial expression was anything but silent. She was glaring furiously at both Dean and Bobby. If looks could kill, someone might have dropped dead at that moment.

It was quiet for a few moments, then suddenly there was a man standing in between Dean and Bobby, and Sam and Jessie. He was clad in a grey trenchcoat, white shirt and navy blue tie.

"Why have you summoned me here, Dean?"

"I was hoping you could help us out with something," he replied.

"What trouble have you gotten yourself into this time?"

He looked like he was irritated by Castiel's attitude, but he seemed to hold his tongue.

"Can you tell us why Crowley is interested in them?" he asked, pointing to his brother and Jessie.

Castiel turned around with a curious look, took a few steps forward, stopping only feet away from Sam and Jessie.

"Nice to see you again, Sam," he said, then turned to Jessie with his hand stretched out in greeting. "We haven't met. I'm Castiel."

Her eyes narrowed slightly, but she managed to keep the majority of the anger from her voice as she spoke. "Yeah, I've heard of you."

He stood with his hand stretched out for a few more moments, before placing it back at his side, looking awkward.

Dean suddenly spoke, explaining everything to Cas, while Sam kept a tight hold on Jessie. She had settled down slightly, but she was still extremely irritated.

Once Dean had finished explaining what he knew, Cas turned to Sam and Jessie again, studying them up and down with sharp eyes.

Jessie suddenly felt inadequate under his scrutiny, making her lean even heavier against Sam.

"I'm not sure what Crowley is up to," Cas said abruptly. "But rest assured I will keep an eye out."

"You have no idea?" Dean asked with frustration.

"That's what I said, Dean," he replied, turning to glance at him sideways. "It was nice to meet you, Jessie."

"Yeah, right," she replied.

She had wanted to say, 'I wish I could say the same,' but somehow it wouldn't come out.

Cas gazed at Sam for a long moment, as if he was scrutinizing him, then turned to Dean and Bobby.

"I will be in touch."

Before anyone could say anything more, he disappeared instantly.

"Well that was anti-climactic," Jessie said sarcastically, as she slipped herself from Sam's hold.

"There you go, Dean. I told you he wouldn't know anything," Sam said shortly.

"Yeah, yeah, good for you. Sammy was right," Dean replied snidely.

"Enough! Both of you!" Bobby said harshly, glaring back and forth at the brothers. "Nothing is ever a waste of time when we're searching for an answer. All of you should know that by now."

His gaze stopped on Jessie, making her avert her eyes.

"I'm gonna need more coffee," she commented to no one in particular.

What she really wanted was a drink, but she couldn't justify drinking shortly after she had awakened, even if it was almost midafternoon.

"I'll go," Dean said quickly, running out the door before anyone could reply.

Bobby was about to say something, when his phone went off. He gave Sam and Jessie an impatient look as he dealt with the phone call.

A/N: So, finally the air has been cleared about her feelings for Sam. How do you think everyone is going to deal with that? And what about Cas? Do you think it was smart to get him involved with whatever Crowley might be up to? We all know angels and demons don't mix.