The first (written) of the Guardian Angel series. Dean said she couldn't have been there with all the things that happened to them and if she was she was a terrible guardian. Here are the times Shiloh and Ruben interacted with the Winchesters without their knowledge.
Takes place before "Exile on Main Street" Season 6 Episode 1
She watched as Dean looked out the front window and glanced down at the salt line. She followed him into the kitchen where he unlocked and relocked the door. This was the nightly routine for the last three hundred and forty eight nights. What Dean didn't know was that the same kind of routine was happening on the street. And Shiloh watched as Sam walked the perimeter of first the street and then of Dean's house. The worst part of this Shiloh though was they were both miserable and yet Sam would just stand in the street and look up and wait for something that never happened. She was beginning to wonder if Sam thought Dean should have felt him and come to him.
Dean was so miserable Shiloh decided it was time to end it and the way things were going that would only happen if she got involved. She glanced up at the ceiling offered a soft smile and a silent promise to her charge before she teleported into the passenger seat of Sam's mustang.
When they pulled up Jonesy's Bar and Grill Shiloh realized she spent too much time trying to figure out what was different about Sam and not enough in how to talk to the man. For what was probably the thousandth time she wished Ruben was here. As Sam's guardian he always understood the younger Winchester better. Although it might not be as hard as she thought since the brothers were drinking at the same bar without knowing it.
She followed the six foot four hunter into the building noticing the subtle changes but not knowing what to make of them. It was a good thing that she could pick him out of a crowd of thousand because tonight the bar was packed. She almost wondered if Dean and Sam had changed bodies with the way the young Winchester was flirting with both the female bartender and women at the bar.
Confident Sam was staying where he was for a moment she headed back to the bathroom. Superman had a telephone booth she had the lady's room. She had found out the hard way just appearing in the middle of the room often caused more problems than it helped. She closed her eyes and concentrated. The body just as she pictured it began to form. She chose a small slight build hoping to grab Sam's protective instincts. For the clothes, she took a little more time. Shiloh chose the traditional hunter's garb of denim and cotton with a few silver additives she wished the boys would incorporate into their clothes. Then she finished the look with a short blond no nonsense hairstyle to sell the idea of a hunter.
She only had to add the weapons to complete the look. In her hand materialized, a blade eight inches long and a Px4 loaded with silver bullets. Not that she needed anything thing more than a touch to kill. A smirk pulled at the corners of her mouth thinking about how many times in the past she had had to prove to the Winchester's that she was one of them. It taught her to cover must be flawless and so it was.
She tucked the knife into a holster in on her back just at the waist and placed the gun in the front pocket of the hoodie she was wearing and stepped out of the stall. A quick glance in the mirror told her she looked like an human and she pulled open the door only to be bumped into by a couple of drunk women giggling so hard they probably did not even notice the collision. Shiloh took a minute to gather her energy and center her being. It took a lot of energy to create a body and as long as she did not have to do anything too taxing to start with, she should be fine.
Back in the interior of the bar Shiloh's glanced to the bar stool she left Sam at to change and found it occupied with a twenty something prep student hitting on a woman who appeared to ignore him. She mumbled a curse in Akkadian and pushed her way through the crowd. She ignored the man now in the seat and walked straight to the center of the room hoping Sam had just moved to a table. A quick scan around the room told her he was no longer in the building.
She hated the limitations that being in flesh created. In her old form, all she had to do was feel for him and she would be where he was. But at this moment it was do things the hard way. By the time Shiloh had pushed her way to the door she was deeply breathing in the night air not because she needed it but because if she didn't she might have turned around and taught those humans a thing or two about respect. Even if she didn't have all of her powers it might been a little satisfying.
When she'd gathered her calm the first thing she looked for was the Mustang. Even if he left with a girl, he would have taken his car. It was one of the first lessons on dating Dean ever taught his brother. Shiloh frowned, as sitting in the same place it was when they went into the bar was the blue muscle car. She took two steps when she heard the thud of someone who kicked a trashcan followed by a very low groan. Another muffled thud followed by the same painful groan made her decide to investigate.
She debated as she walked down the alley. She wasn't interested in watching a couple of humans having sex but with Sam missing Shiloh was not just going to ignore it either. Halfway down the alley she saw two men pinning the youngest Winchester against the wall.
"Hey," Shiloh yelled recklessly.
When the two men holding Sam turned and looked at her the eyes flashed blue and Shiloh knew immediately what was after him. Disgusting parasites from her own land and not just for the second time tonight did she wish she were in her old form. She would have squashed those two like the bugs they were.
One of Djnn continued to hold a limp Sam against the building while his partner started in her direction. Shiloh only had a moment to decide what to do and what she decided wasn't what she wanted. She pulled the Px4 from her pocket and fired a round into the chest of the advancing monster. The bullet didn't faze him and that didn't surprise Shiloh at all since the thing was designed as window dressing and not to actually use. She would not be making that mistake again in the future. She didn't play this time just as the Djinn got close Shiloh allowed her power to leak from the human creation she made. Through a white haze, she could see the shadow outline of her four wings on the building walls.
She didnt know if the Djinn decided tonight wasn't a good time to try their luck or that they just finished what they started and didn't need to stick around but the one holding Sam patted his face and dropped him in a heap before following his brother across the alley. She thought it was more of a challenge, save the human or catch us. They most likely though she would be like normal angels and avenge the dying human. What they didn't know was how much this human meant to her alive. Or that they gave away who they were when they looked back one last time and Shiloh noticed the family tattoo for the first time.
She reminded herself how much she hated revenge and rushed forward to aid the poisoned hunter. He was already beginning to mumble answering what ever fantasy or terror the poison created. If she had been, human this would be the time she would start praying but even she knew that was useless. She did on the other hand hope her luck held out and no one came down that alley until she was done. It was going to take a lot of energy to heal him, transport him to his car, and continue to be human.
She touched his forehead and a white light started getting brighter and brighter until the area was completely lit up. Then as suddenly as it started, it was black again and the human was breathing a lot easier. Sam started to open his eyes when she muttered the word sleep with her hand still on his head. She only needed him out for a minute so he would believe she used an antidote on him and to teleport him to the car.
Back at the mustang Shiloh marveled again at how much her powers made difficult things easy. She had not been looking forward to wrestling his large frame into the little bitty driving space. But this way was good. She manhandled him enough to fish the keys and wallet out of Sam's pocket and left the leg hanging out the door and the door open. Shiloh dropped both in his lap so he would know she had gone through his stuff. The scene set she leaned backwards against the back door and waited for the Winchester to wake up.
Shiloh heard him groan twice before she pushed herself off the car and stood in front his door.
He might have just been poisoned and left for dead but he was which why no sooner had he opened his eyes he had his gun in his hand, cocked and aimed at her.
"Dude," Shiloh said with a light west coast accent. "Is that anyway to treat someone who just saved your life? I am Shy by the way."
Sam scoffed and then frowned. The last thing he remembered was hanging up with Samuel outside of the bar before two large men drug him down the alley. He would have said werewolf if it had just been one. Yet here he was sitting in his car. "Yeah and how did you do that, Shy."
Shiloh laughed, pulled the gun from the hoodie pocket and said, " oh just a little gun powder and silver. It tends to deter most things, especially the supernatural kind."
Sam frowned again as he tried to remember shots fired and couldn't. His arm had begun to shake and he brought the other one up to steady it. That put him in an awkward position that would make it difficult to shoot if he needed too. He watched as she put her piece back in her sweatshirt and bounced on her toes just like a kid.
Shiloh wondered if Sam was going to buy it or not. Hunters lied for a living and expected that everyone else did. If she volunteered information he was not going to believe it but if he didn't ask she couldnt tell him and tonight would be for nothing. "Look dude, I know you Winchesters are a big deal, or so says Bobby. So I would hate to have to kill you after saving you. And if you don't put the gun down I am going to have to assume your going to shoot me. Then I will have to defend myself and kill you. And that means I am going to have to look over my shoulder for your vengeful brother for the rest of my life. I don't want that I have enough to do to watch my back."
"Wait you know Bobby?" Sam said as he lowered the weapon slightly as the name of the old hunter registered with him.
"Yeah," Shiloh said in a tone that suggested Sam should have known this. "Bobby Singer, he covers all the hunters official calls. He is also one hell of a research assistant."
"You're a hunter?" The disbelief in Sam's tone told her that he had accepted her story.
"What's the matter hot shot? Don't think girls can hunt? It wasn't me passed out in the alley over there from Djinn poison.
"So that's what happened to me," Sam said putting the gun down completely and rubbing his head. "And you just happened to find me while you were out hunting."
"Of course not. Well kind of. I was hunting a group I had tracked from Joliet, Illinois and I did stumble on you, but I didnt know who you were. I just knew that they were luring people from bars for a little dinner to go. The funny thing is it didn't look like they were planning to eat you. From what I could tell just pump you full of poison and watch as you died."
Most of her story sounded like the truth but there were still a couple of things nagging at him. One how did one girl get rid of two Djinn, how was he still alive and what was he doing in his car. He had a feeling there was more to this story, he just had to get it. "So if they were enjoying themselves why did they take off? Not to say your not a good hunter but you were out numbered."
"I was and while silver bullets doesn't kill them have you ever seen what the antidote to their poison does to them?"
"There's an antidote?"
"Dude, there is an antidote to almost everything. That is if you take it in time. You're just lucky I had my 'in case of emergency one on me.' Or you would have been toes up. I am glad your okay and all but I have a couple of Djinn I have to track. I would like to get back to California before spring break hits."
By this time, Sam had climbed from the car and was leaning against it. He was still trying to decide if he should trust her. If she was really a hunter maybe she would like to join Samuel and then they would stop making comments about him going to see Dean. "I know most hunters work alone but I hunt with my family. Would you like to join us?"
Shiloh knew the invite for what it was a chance to test to see if she was who she said she was. And of course she would fail that test. "You mean meet the famed Dean Winchester? I don' think so. I'm sorry I am sure Bobby knows you better than I do but from what I saw tonight the rumors about you have been over hyped. You're sloppy and he well ... where is he?"
"Dean doesn't hunt any more," Sam said with a little more longing than he meant.
"Oh. ... Um I... look I am sorry but the answer is still no. I have been working alone since my partner was killed two years ago. " Shiloh had not meant to say that. Ruben was a sore subject for her and talking about him would only cause issues right now. "I am going to go now. The trail is getting colder so to speak and I want to make sure they haven't left town."
Not happy with the woman's decision but without kidnapping her there wasn't a lot he could do. Maybe if he stuck to investigating the Djinn he would find her again. He missed hunting with a partner and she would do for a while.
She walked about fifteen feet, stopped turned around and said, "hey Winchester, just in case you weren't a random target tonight you might want to watch your back a little closer. Those Djinn were after more than a quick meal. That or get your brother back in the life. After all what monster wouldn't want to take out the big bad Winchesters especially if they are separated. Oh and if you are ever in Carlsbad look me up maybe we could grab a burger."
This time she continued to walk and didnt turn around even when she heard the engine turn over. She knew what was going to happen from past experience what was going to happen. Sam would go get his brother. Dean would stop pretending to be something he wasn't and they would be one big happy family again. She had to admit the Djinn showing up had worked better than her original plan. Sometimes being a guardian angel was an easy job.