Requested by: Kaddiy_Dreams

Imagine: When Dean is dead you and the Trickster become best friends, but soon you start to fall for him.

You were alone in a bar, drinking away the pain. Your older brother Dean had died only two weeks ago, and the pain you were feeling was unbearable. Not only did you lose one brother, but wben Dean died, you also lost Sammy, who left you to deal with his sorrows in his own ways.

So, you were all alone...sitting in a bar. You had at least out enough energy into your appearance to look hot, and every few minutes a new guy was hitting on you. After a couple of hours, it got really annoying, so when you felt another person sit down next to you, without even looking, you said, "If you don't leave right now, I will hurt you."

"Someone's grumpy," the man teased causing you to look at him. "Gabriel," you muttered under your breath. "Hello, Y/N," Gabriel replied sweetly, and you just rolled your eyes at him in response. "You don't like me very much, do you?" Gabriel asked. "You killed Dean over and over again and then trapped me and my brothers in TV Land Hell. Why should I like you?" you inquired.

"Because I'm only here for you," he told you. "What do you mean?" you asked. Gabriel looked down for a split second before returning his gaze to you. "I know that when you lost Dean, you also lost Sam, and I don't want you to be alone," Gabriel explained. You looked at him skeptically before asking, "Why do you suddenly care?"

"It's not suddenly, I've always cared. I just haven't been as open about it," he replied. "Really, Gabriel? When did you ever care?" you questioned. "Well, the only reason I put you through the pain of watching Dean die over and over again is because I thought that if you felt the pain over and over again, then when he actually died, it wouldn't be as bad," he justified.

"Well, it didn't work," you responded. "Which is why I'm here now. I want to help you," Gabriel told you. "Really? How?" you asked, curious. "By reminding you of who you are. You aren't someone who goes to bars every night to try and forget the pain. You're a badass hunter who faces the pain, and conquers it," Gabriel told you with a small smile.

"And how exactly are you planning on reminding me of this?" you questioned with a small smile dancing lightly on your lips. "Do you trust me?" he asked. "Should I?" you responded. Gabriel held out his hand, and said, "50/50 chance. If you come with me, I promise, you will either have an amazing time, or you will want to kill me. Either way, you aren't sitting alone in a bar getting drunk, and yelling at every guy who comes up to you."

You chuckled softly, before placing your hand in his. "You have one shot, don't screw it up," you told him. "Don't worry. I'm an archangel, I don't screw anything up," he replied arrogantly, making you laugh, which in turn caused him to smile. "Ready to go?" he asked you, and you nodded your head.

He then laced his fingers with yours and then snapped once. In an instant you were in an abandoned warehouse. "Gabriel? Where are we? If you're planning on killing me here, I'm pretty sure it was a bad idea to trust you," you whispered, not sure what was lurking in the shadows of the deserted building. You could still feel Gabriel's hand laced in yours, and chills went down your spine as Gabriel bent down and whispered in your ear, "We are in a vampire's nest. They are all sleeping in the next room. This is who you are, Y/N. I'll be here if you need me," Gabriel told you, before placing a machete in your hand.

You looked at the machete and then back at Gabriel who motioned for you to go on into the next room and kill the vampires. You took a deep breath before entering the next room. You scanned the room quickly. There looked to be about eight vampires, a small nest, but still enough to take you down if you let them.

You started to quickly slice off all the vampires' heads, and you took care of the first four, when there was suddenly a noise from outside. You had no idea what it was, but it was loud enough to wake up the other four vampires, who looked around their nest, and were furious to see the heads of their other members cut off, and you standing in the center of the room, machete in hand.

As if on cue, they all jumped out of their hammock-like beds, and launched towards you. But, as Gabriel said you were a badass hunter, and knew exactly how to get out of this situation. You finished off three of the four vampires, but the last one, the largest, toughest one was still left, and he had disappeared.

You looked around the room, but you couldn't see him, as soon as you turned back around, he attacked. He was about to get a hit on you, when all of a sudden he glowed brightly before dropping to the floor, dead, as Gabriel stood behind him, with a small smile on his face.

"I told you I had your back," Gabriel said. "I didn't need your help. I was just a little out of practice," you told him. "Y/N, you killed seven out of eight vampires by yourself. If that's a little out of practice then I would hate to see you're A game," Gabriel responded, making you a proudly smile. "And by the way, would it kill you to say thank you?" he teased.

You now fully smiled, enjoying being here with Gabriel. "Thank you, Gabriel," you told him. "Your welcome," he replied, before you and he made your way out of the building into the cold night air. "So, tomorrow, I'm thinking we go to New Orleans, and hunt some demons," Gabriel suggested.

"Tomorrow? Why wait?" you replied with a warm smile. "Really? You aren't too tired?" Gabriel asked. "I'm Y/N Y/L/N, I don't get tired," you joked, making Gabriel chuckle. "Look, if I get too tired after the hunt, you and I could just stay at a motel," you proposed. Gabriel looked shocked, but didn't say anything. He just nodded his head, silently agreeing. "Well then, ready to go?" he asked. "Always," you responded, and he smiled as he once again snapped, transporting you to New Orleans.

~Time Skip: 6 months~

You and Gabriel had been hunting together every day for the last six months, and you have enjoyed every second of it. You and Gabriel have gotten close, and if you were being completely honest with yourself, you had feelings for the archangel.

Gabriel was watching TV in the living room of the motel, while you were in the bathroom, making yourself look amazing, because you wanted to go out tonight, and you were going to beg Gabe to go with you. When you were finally finished, you walked back out into the living room, and Gabriel whistled. "Someone looks very hot tonight," Gabriel told you, making you slightly blush.

"Where you headed?" Gabriel asked you. "We are going out tonight," you replied. "We?" he questioned, raising an eyebrow. "Yep, I'm making you come with me, because I'm bored, and we have no hunts to go on at the moment," you responded.

"Alright, where are you taking me?" he asked you, and you went a little quiet. "I don't know yet," you replied, a little quietly, making Gabriel laugh. "You know what, I have a place in mind," he told you. "You do?" you questioned. "Yep, we can go there right now, if you want," he said.

"Yep, let's go," you told him, and he stood up and walked over to you. He laced his hand with yours and then snapped his fingers. The next thing you knew, you were in the middle of a huge fair. It was nighttime so everything was beautifully lit up, and you were a bit taken away. "Is this good enough?" Gabriel asked, holding his breath as he awaited your answer.

"It's perfect," you said, and he allowed himself to breathe again. You never let go of Gabriel's hand, instead, you dragged him to the nearest booth. In this booth, you had to shoot ten baskets in thirty seconds to win the grand prize. "Care to put your archangel mojo to the test?" you asked Gabriel.

"Please, I could do this in my sleep," Gabriel responded. "I thought angels didn't sleep," you retorted. "You know what I mean," he responded, making you laugh. He paid the two dollars to the booth manager, and then the clock started. Gabriel was actually doing really well, so you decided to mess with him a little bit. You stood really close to him, so close you could feel the heat radiating off of his body.

Gabriel was almost immediately distracted by your proximity, and he looked over to his side, at you. "What?' you asked innocently. "You're distracting me," he told you. "I thought you were a big, bad angel. Surely, you could still make baskets with me standing here," you teased, making Gabriel let out a sigh.

"I can, actually," he replied. "Well, go on, show me then," you coaxed, and he went to shoot the ball, but he missed. He let out a sigh as the buzzer rang, and smile spread across your face as Gabriel made eye contact with you, looking playfully mad at you.

"Awe, what's wrong Gabe?' you asked. "You cheated," he told you. "I didn't cheat! I just wanted to get a better look at your technique," you responded. "Well, you must be blind if you had to get that close just to see how I shoot a basketball," Gabriel countered making you laugh.

"Well, maybe, I just wanted to be close to you," you told him, your face going serious, and Gabriel felt his heart rate increase dramatically. "What?" he asked, and you once again walked up to him, until your face was mere inches away from his. His breath hitched as you leaned in, until your lips were barely touching, before you looked over Gabriel's shoulder, and asked, "Is that cotton candy?"

You quickly pulled yourself away from Gabriel as you started to bound off to the cotton candy. "Oh, you are so going to pay for that," you heard Gabriel say as he followed you, making you smirk. He looked flustered and frustrated as you got your cotton candy. "What?" you asked him.

"Nothing, I just thought we were having a moment," Gabriel told you. "We were, but what can I say, my lips wanted you, but my stomach wanted the cotton candy, and my stomach controls my mind," you said with a smile, and Gabriel shook his head at you, trying not to laugh.

"Do you want to play some skee ball?" Gabriel asked, as he gestured over towards the five skee ball games that were set up. "Sure," you replied, as Gabriel led you over to the game. "You go first," he told you. "Okay," you replied, as you grabbed a ball and rolled it up the ramp, and scoring the lowest possible score. You looked down, slightly embarrassed, and Gabriel asked, "Have you ever played skee ball before?"

"I'm a hunter, what do you think?" you replied, a little sheepishly, and Gabriel chuckled. "Awe, Y/N, you're so adorable. Come on, I'll show you," he told you, as he came up behind you, pressing his chest into your back.

He grabbed a ball and placed in your hand, before wrapping his hand around yours, and placing his other hand on your waist, making you blush hard. He placed his head at the side of yours, and then brought your arm back, and quickly rolling the ball back up the ramp. You hit the highest hole, and you smiled happily, as you turned to face Gabriel, not realizing your face was still red from the earlier placement of his hands.

"Are you okay Y/N? You look a little flustered," Gabriel told you. "I'm fine," you responded. "I don't think so, maybe you have a fever. Let me check," Gabriel told you as he placed both of his hands on your waist, pulling you close to him. He slid his right hand up your body until he reached your forehead, making your heart skip beats.

"No fever. Which means it's okay to do this," Gabriel said before sliding his hand back down to your waist and leaning in. It was your turn for your breath to catch in your throat, and right when Gabriel's lips were about to touch yours, Gabriel made a quick move, and started tickling you .

You squealed as you jumped back from Gabriel and smacked his arm. "Gabriel!" you complained. "What? To did it first!" he retorted, and you made a really cute said puppy dog face. Gabriel laughed before saying, "Come here." Gabriel pulled you close once more, but this time he smashed his lips to yours. Fireworks exploded as Gabriel and you both held your breaths.

When Gabriel pulled away it was only because he needed air. He looked at you speechless, and without even realizing he way saying it, Gabriel blurted out, "I love you." You looked at him shocked at how forward he was, and his eyes went wide as he realized what he said. You could tell worry was starting to build up in him, so you reassured him by replying, "I love you too, Gabriel." The biggest smile appeared on Gabriel's face, as he pulled you into another passionate kiss, never happier, because he knew he had the perfect girl, the girl he would always love, and the girl who would always love him.

Hello my little monsters,

I hope you guys liked this one. Let me know what you thought. Sorry for typos! As always, thank you all for reading. I love you all and all of you are amazing!

Always Keep Fighting!