"Thanks for the orange juice, Jude," Victoria said, sitting up in bed and sipping some of the orange juice out of the glass.

"No problem. Do you need me to get you anything else?" Jude asked.

"Look at you, Dr. Winchester. Bed side manner is a check. Just don't know about your actual doctoring seeing as the last time I checked orange juice never really actually cured sick patients," Victoria teased.

"Hey, I'm just being a good big brother, okay? You're already hyped up on Sudafed. There's… not much more we can do," Jude replied, saying the last part dramatically.

"Por que?" Victoria cried out dramatically. "Oh, that's gross. I'm so congested."

"The Sudafed should kick in at any moment," Jude chuckled. Jude made to leave but Victoria said something before he could actually go.

"Could you stay here with me? Tell me about college. Anything to distract me from my impending death," Victoria groaned, sniffling. Of course, it didn't work and she could barely breathe out of her nose. She was hyped up on Sudafed and knew she'd be out soon enough.

"Victoria, you're not dying. You have a sinus infection," Jude reminded.

"Yeah, whatever, Dr. Winchester. Hey, that's actually kinda cool. Speaking of, tell me about docterly things. Please, Jude," Victoria begged, desperate to get her mind off of her sinus infection. "I barely got to say goodbye to Tyler. Please distract me!"

"Alright, fine," Jude chuckled, rolling his eyes playfully. Damn. His baby sister had a boyfriend. Now this was news. "I-, there's not much to tell. College is… college. It's been the same as usual."

"Come on. There's gotta be something…" Victoria trailed off, doing her best attempt at her cousin's trademark puppy dog eyes. They didn't work as well for her but at least she could say she tried. "You're a Winchester. There's gotta be a girl! There's always a girl." Jude laughed, shaking his head but not responding. Victoria's eyes widened as she sat up even more. "Oh my God, there is a girl, isn't there? And you don't want to tell us about her because you know we'll want to meet her… which means it's serious! Oh, and of course you don't want her to meet your big, crazy family out of fear that we'll scare her off. Yeah, okay, I get it. You're ashamed of us but the least you could do is tell us! Tell me. Please?"

"You know, Dad keeps telling me that you're growing up faster every day but you still manage to act like my annoying little sister no matter how old you get," Jude teased.

"You love me," Victoria shot back, playfully.

"Ah… you're right. Damn it," Jude swore under his breath, jokingly.

"Hey!" Victoria exclaimed, punching him.

"Ow! Wow, that right hook of yours is getting better too. Maybe I shouldn't leave for college anymore," Jude said.

"Why thank you," Victoria said back, proudly. "Don't change the subject, Jude. Tell me about this girl. I won't tell anyone and you know how good I am at keeping secrets."

"Victoria, it's not-," Jude started.

"Sick sister, remember?" Victoria interrupted.

"Wow, you really are sending me on a guilt trip, huh?" Jude asked back. Victoria nodded and Jude laughed, rolling his eyes. "You and Dad both… anyways…" Jude sighed before continuing. "Yes, there is a girl. Well, was."

"I knew it! I knew there was a girl!" Victoria exclaimed.

"Do you want me to finish this story or not?" Jude teased.

"Fine," Victoria said, narrowing her eyes at her brother. "So how'd you meet her?"

"I met her in Peru…"

~Flashback~

"Alright people, we've got to go. People's lives are on the line. Winchester and Peterson, you're with me. Caldwell and Laurence, you're with the other Dr. Morales, and Thomas and Williams, you're on clinic duty. You got that?" the female doctor asked, ordering everyone around. There were nods and mutters of 'yes' in response before they decided to split up.

"Peters, Winchester, give me us a minute would you?" the woman asked, before heading over to the tall, Colombian man.

"Hey, I'm Jude," Jude introduced, turning to the girl next to him. She had long black hair, pulled up into a ponytail and beautiful green eyes. He couldn't help checking her out. It was in his blood. He tried to shake it off, but it didn't work, so he at least tried to make it not so obvious.

"Anna Peters," the girl replied. She didn't so much seem to mind that he was checking her out because she seemed to be doing the same thing.

"Nice to meet you," Jude said, extending his hand for her to shake. She took it, smiling at him.

"You too. How lucky are we? First day and we're already working with Dr. Jennie Montgomery," Anna said.

"Uh… this is kind of embarrassing, but fill me in on the details? I mean, I know she's like medical royalty," Jude started.

Anna chuckled, "It's fine. The only reason I know is because my parents are friends of theirs." Anna nodded towards the couple as they talked, delegated what needed to be done. Those are the Moraleses. She and her husband Daniel are practically surgery gods! Just so that things are less on confusing, she usually goes by Montgomery instead but she did take Daniel's name. She came to this same program as a surgeon and they got married. They went back to the states for a while but came back about five years ago to run this place once the previous director resigned."

"Gotcha. Morales… I think I may have read an article in a medical journal about some breakthrough in cardio thoracic," Jude started.

"That's most likely her," Anna replied.

"So uh, you're family friends?" Jude asked, curiously.

"Not really. Well, sort of. My parents are just like them but you know, without souls," Anna replied.

That caught Jude off, causing him to laugh, "Oh, come on. I'm sure they're not that bad."

"Oh, you don't know my parents," Anna said. She laughed a little. "But I'm not about to tell you my entire life story. I just met you." Jude looked around to see that Montgomery and her husband were still talking to each other.

"Alright. Well, how about after all this, you and I head over to the cantina and grab a couple of beers?" Jude suggested.

Anna giggled, shooting him a funny look, "Did you just use a line on me?"

Jude sighed, "Yeah, it's kind of in my blood."

She smiled a sweet smile, looking up at him out of those beautiful green eyes, "Okay, but under one condition."

"What's that?" Jude asked back.

"I tell you my life story and you tell me yours," Anna replied.

"Fair enough," Jude answered.

"Alright then. Let's hope we make it through the day," Anna said, a small smile playing on her lips. She looked to see that Dr. Montgomery was heading towards them.

"What's that supposed to mean?" Jude asked back, curiously. This girl was a firecracker.

"Being out in the jungle – not so easy," Anna answered.

"Alright, you two ready?" Montgomery asked.

Anna and Jude exchanged glances before replying, "Yes."

~End Flashback~

"I can't believe you just asked her out like that!" Victoria exclaimed, laughing.

"Like I said before. It's in my blood. It's a Winchester thing," Jude defended himself.

"Yeah, but at least she took it well. You make it sound like she was checking you out too," Victoria replied.

Jude shrugged, "What can I say? I'm a good looking guy, Vi."

"Oh, and looks like you inherited Dad's modesty quality too," Victoria teased.

"Yeah, whatever," Jude said, rolling his eyes.

"So what happens next? Did you guys get those beers?" Victoria asked.

"Yeah, we did," Jude answered.

~Flashback~

"Que querian hoy?" the bartender asked.

"Me gustaria una cerveza para mi, y una cerveza para mi amigo, por favor," Anna ordered.

"Bueno, senorita. Tendre las cerveza en uno momento," the bartender replied.

"Gracias," Anna answered. She looked to Jude to find him just staring at her in amazement. "What?"

"You speak Spanish?" Jude asked, impressed.

"Yeah, I took it in high school and then did a study abroad program my sophomore year for a semester in Spain," Anna answered.

"Wow," Jude managed to say.

Anna narrowed her eyes at him, "What? Are you going to say that you find that incredibly sexy?"

"Actually, yes," Jude answered.

She laughed, "Jude, Jude, Jude… so predictable," she teased.

"I'm kidding! Seriously. What I was going to say was that it was impressive. I don't think I could learn another language like that," Jude said.

"Immersion is key. I would offer to help you out, but I'm still learning myself. Spanish in Spain is pretty different than here," Anna replied.

"Oh yeah? See, I didn't even know that," Jude replied.

"That must be because I'm smarter than you," Anna joked, straightening up.

"Hey, no one said anything about that," Jude said.

"I'm a girl. It's a given," Anna said.

"Wow… now you want to play the girl card. Can't say I didn't see that coming. Guess you're the predictable one know," Jude said back.

Anna raised an eyebrow but before the bartender came back with their beers.

"Una cerveza para la hermosa dama y la otra para la cerveza de el hombre que está tratando de entrar en los pantalones," the bartender said, placing both beers down.

"Gracias," Anna replied, her pronunciation perfect.

"Gracias," Jude added, nodding once to the guy. They both took a sip of their beers before Anna began laughing. The bartender hadn't left yet and was eying Jude funnily.

"Cuidado, senorita," the man said, before finally leaving. Anna began laughing as Jude looked from the bartender who was helping someone else, and Anna.

"What? What'd he say?" Jude asked.

"Nothing. He just thinks you're trying to get into my pants," Anna replied.

"What?" Jude exclaimed.

"Well, are you?" Anna asked, flirtatiously challenging him.

Jude bit his lip, "Depends. I haven't heard your life story yet which is what we originally decided to do here. You know, I gotta make sure that after we hook up, you won't go all crazy, possessive, girlfriend on me."

"Who says we're hooking up?" Anna challenged. "And besides, if anyone was to go all 'crazy, possessive' on anyone if we hooked up, it'd definitely be you."

"I'll hold you to that," Jude answered, smirking.

"You really want to hear my life story?" Anna asked, changing the subject.

"Yeah, why not?" Jude asked back.

"Okay, but if you want to kill me by the end because I'm so boring or you get so sick of me, I can't say I didn't warn ya," Anna started.

"I won't," Jude chuckled.

"Alright," Anna said.

"Oh, and Anna?" Jude asked.

"Yeah?" she asked back.

"For the record, I do find you incredibly sexy," Jude replied. "Damn it. See? There I go again. It's… kind of genetic… the forewardness." Jude rolled his eyes as he couldn't believe he had said that. In his late years of high school and early years of college, stuff like that never bothered him but he had grown up since then. Or at least he thought he had.

Anna opened her mouth to say something but nothing came out of her mouth. She tried to hide her smiled, shaking her head. Instead of answering Jude, she continued her story. God, this boy was going to make this summer interesting for her.

~End Flashback~

"Jude, you fox!" Victoria teased.

"I just kind of blurted it out," Jude shrugged.

"Okay so what happened next? It sounds like she was into you," Victoria asked.

"We worked together every day and things got kinda… you know… flirty. We got pretty close too. I think she was worried that the attraction was just physical but it was so much more," Jude replied.

"Oh yeah?" Victoria asked. Jude nodded slowly. He hated that he sounded like such a girl, talking to Victoria about this but he couldn't help himself. He needed to sort out his feelings for her soon before it was too late.

~Flashback~

"Holy shit. Jude. I- I can't go out there," Anna stammered, sitting on the floor in one of the medical supply closets. "I can't. My parents are world class surgeons. I can't face them. They're going to have expectations and, well, you know, it's not like I'm making breakthroughs or anything here and-."

"Anna, stop. Look, I know you're freaking out but you're forgetting something else. Your parents are your parents. Don't you think they may have come here to see you, not just to check up on progress you're making in your career?" Jude asked.

Anna shook her head, "Jude, my family's not like yours. We don't do that kind of stuff."

"Yeah, well maybe this is their way of doing it," Jude said.

Anna just looked up at him. He had a point and she had to admit that she loved seeing this side of him. She had seen that flirty side of him when they were at the cantina with friends, the friendly side of him when they were working, and the doctor side of him when they were out in the field, which she happened to find incredibly hot. But this side, the comforting, caring one. She had only seen him like this with patients but with her… he really cared for her, didn't he?

"Deep breath, okay? Come on. We'll do it together. Just introduce me as your friend. I'll be with you the whole time," Jude comforted.

"You'd do that? You'd endure a whole dinner with my crazy parents?" Anna asked.

"Of course," Jude said. "Look, you're my best friend here. I care about you."

Anna smiled, "Thank you."

"Come on," Jude urged, offering his hand out to her. She took a deep breath before taking it, Jude helping her up to her feet. "And if they try to give you a hard time, don't worry. I'll tell them all about their amazing, sexy, talented doctor that is their daughter."

Anna laughed, rolling her eyes, "Can you leave out the sexy part? Maybe not parent appropriate."

"Just a little bit," Jude replied, sarcastically.

Anna laughed again, "Thank you, Jude. You don't know how much this means to me."

"It's no problem," Jude replied. And it wasn't. It was all true. He cared about her.

~End Flashback~

"Aw, Jude that's so sweet, but get to the good part. Please tell me you kissed her," Victoria said.

"Yeah, that did happen…" Jude chuckled, fondly remembering their first kiss.

~Flashback~

Jude and two of his friends were walking back from the beach, shirtless. As they approached the cantina, Anna and a few of the people she was sitting with at the bar spotted the three men.

"Damn, Jude Winchester. God he's sexy," Erica smirked.

"Yeah, too bad he only has eyes for Anna," Chelsea added.

"What? He does not!" Anna protested.

"Uh, yeah he does. We see the way he looks at you. Girl, you lucked out. Not only were you assigned to work with Dr. Montgomery Morales but you get to work with Jude every day," Chelsea sighed, staring at Jude.

"Guys, there's nothing going on between Jude and I," Anna denied, even though she doubted her denial.

"Prove it," Chelsea urged.

"Yeah. Go over and kiss him. If there's nothing there… well then I'll go for him," Erica challenged.

"Fine," Anna said. She got up, marched right up to Jude and kissed him. Wolf whistles and cheers came from the other people in the bar before Jude pulled away.

"Anna!" he exclaimed, shocked, a smile appearing on his face.

"What? I thought you found me incredibly sexy. Your words not mine," Anna smirked.

"I do but-," Jude started.

"Then kiss me," Anna replied. She was testing. After that kiss, she knew her feelings for him. So what were his? Jude was still in shock. She stared at her long and hard before kissing her. Anna kissed him back with just as much force and passion that he kissed her with. Jude pulled her a little closer to him. Finally, the two pulled away from each other just looking at each other.

"How come we waited so long?" Jude asked.

"I have no idea," Anna replied. All this time, they had tried to keep things professional, but now they couldn't figure out why.

~End Flashback~

"Tell me more," Victoria said, drowsily. She was falling asleep but still wanted to hear more. Stupid Sudafed. She was determined to stay up long enough to hear the end of the story.

"Okay…" Jude trailed off.

~Flashback~

Jude walked by the cabin that Anna shared with two other girls because it was on his way. It was late at night and he figured no one would be up but was headed towards the beach. He continued walking and froze when he heard footsteps behind him.

"What? Scared of the dark?" he heard the all too familiar voice ask. A smile spread across his face as he turned around to see Anna walking towards him. "Heading to the beach?"

"I didn't mean to wake you up," Jude started.

"You didn't. Come on," Anna said, grabbing his hand as they walked together down to the beach. Ever since their kiss in the cantina a week and a half ago, Jude and Anna had been a thing – well as much as a thing that a summer fling could be. The both of them knew that this wasn't permanent and were just enjoying each other. As soon as they reached the beach, Anna dropped the towel that was in her other hand and headed towards the ocean, Jude right behind her.

"You brought a towel?" Jude asked, seeing the towel in her hand.

"Thought we could go swimming," Anna said.

A smirk spread across Jude's face, "I like how you think."

"I thought you would," Anna answered, before lifting her shirt over her head. Jude took off his shirt and heard a crash in the ocean as he saw that Anna had beat him to it, stripped all the way down and run into the water. Jude shook his head. Damn he was lucky. He pushed his shorts and boxers down before chasing her into the water.

~End Flashback~

"Woah! Jude, way too much information," Victoria said.

"I thought you were sleeping," Jude said back.

"No. Now tell me something else so I'm not scarred for life," Victoria begged.

"Fine," Jude sighed, still dwelling on their night together. He'd never forget that night they spent together. After that, they went back to the cabins, took a shower, and since Jude's cabin mates were all out, they spent hours together in that cabin… not sleeping.

"What happened in the end?" Victoria asked.

"We ran into a demon in the field… I hunted it and I kinda had to tell her the family secret," Jude confessed with a sigh.

~Flashback~

"You what?" Anna exclaimed.

"Look, this doesn't change anything. I'm still me. I-, it's just that my family… we know things that other people don't. We know about angry spirits like the one we met back there, werewolves, shapeshifters, vampires…" Jude attempted to explain.

"Those are real too?" Anna asked, her eyes widening.

"Yes, but my family, we hunt them. There are other people like us out there too," Jude said.

"I-, I don't know what to say, Jude," Anna said.

"Anna," he started.

"I, give me time to think, okay? I just, I don't know what… what you just told me…" Anna trailed off.

"What so you don't believe me? You think I'm making this up?" Jude asked, defensively.

"No! Of course not. I mean, after what we saw? I just, I think we should take time off. I need to think and this program is almost over so maybe it'll be good. We can adjust you know, if we take a break and-," Anna started.

"Are you breaking up with me?" Jude asked, hurt.

"I guess, yeah. But just for now. Just until-," Anna started.

"Yeah, okay. I guess we weren't really much anyways. We never… defined anything," Jude said.

"Jude, don't say that!" Anna protested, her eyes welling up with tears.

"It's true right? It's easier for you, right?" Jude asked back. He hated that he was acting this way but it only because he was hurt. He cared about her and after opening up and sharing with her one of the biggest parts of his life, she was shutting him out. And that sucked. A lot. He knew it was a lot to take in but to break up with him like that? That really sucked.

"Jude," she pleaded.

"I should go," Jude said, avoiding eye contact.

Anna held her ground. She wanted to ask him to stay. Say she was sorry but she did have a point. This program would end soon and they'd go back to their normal lives. She was transferring schools and she had no idea where it'd take her. There were acceptance letters waiting for her at home and she'd have to see then. There was no way that she could bank on being with Jude. She had to just let him go and maybe, just maybe after she was done thinking, she'd be able to say goodbye to him properly. For now, this would have to do. They had one more week to say goodbye.

~End Flashback~

"And you left early! You didn't even say goodbye, did you?" Victoria asked.

"Yeah," Jude sighed. Victoria then smacked him across the shoulder. "Ow!"

"Jude, that was such a dick move," Victoria chastised.

"I know, I know. But we worked things out. She's at Drexel now and… we're friends," Jude answered.

"Right. Because that worked out for you the first time," Victoria said, sarcastically.

"What's that supposed to mean?" Jude asked.

"Look, it's obvious you still have feelings for her. She's at your school and frankly, I wouldn't be surprised if she picked Drexel partly because of you. Whether it was to get closure or because she still has feelings for you too… I don't know. She must care about you a lot to follow you all the way to Pennsylvania," Victoria replied, honestly.

Jude knew his sister had a point, "Damn it. Why are you so smart?"

"Because I'm your smart ass little sister," Victoria shrugged.

"So you think I should… you know go for it?" Jude asked.

"Yeah," Victoria answered in a 'well-duh' tone.

Jude laughed, rolling his eyes, "I don't know. Taking advice from a fourteen year old is a little risky."

"Hey, I've got the successful, happy relationship here. You should probably listen to me," Victoria said.

"Woah! I don't appreciate that sass, missy," Jude teased.

"Come on, Jude. Don't be a chicken. Just give her a call. Let her know you still care about her," Victoria encouraged.

"You know, that's not a bad idea," Jude sighed.