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Description
Dean was gone.
It was less than two weeks since that bitch Lilith collected on Dean's contract and had her dogs drag him to hell.
Two long agonizing weeks without your best friend.
You couldn't make it to his 'funeral', you had a nasty vengeful spirit you had to deal with in Reno. After that you went straight to Bobby's where you did nothing but drink and mourn with the old man.
Sam wasn't there, and he wouldn't answer his damn phone. For all you knew, he was lying dead in a ditch somewhere. Or caught in some vampires nest without back up. Maybe hung up in some nasty warehouse where a Dijin was feeding off him.
All the scenarios you come up with made you cringe.
Please don't be dead.
You took another swig of whatever you had found at Bobby's, it went down rough, but at this rate you didn't care, it did the job.
Feeling the warmth seep into your bones, you relaxed thinking about the last time you saw Dean. You had swore to him you'd look after Sam, and Bobby. So far you were doing a top notch job.

*Flashback*
You sat in a both at a local diner, laughing at Dean from across the table as he wiped the remnants of his dinner off his lap.
“It's not funny (nickname).”
And still you laughed, clutching at your sides that hurt.
“Laugh it up, you know what they say about payback.”
It was still another minute before you sobered. “Sorry, b-but you'd be the only one...” You were cut off as you broke out into another fit of laughter.
“Shut up.”
“Hey, at least it wasn't in baby.”
Dean paled at the mere thought.
You had met with the Winchester boys, investigating the same case.
You had a lead, but there was nothing you could do till the morning, so Dean suggested you go out and catch up since the last time you actually saw him was back at the Roadhouse months ago. Sam declined, wanting to do more research.
Little did Dean know is that you were helping in Sam's research project, and it wasn't on the case. No, you knew Sam was looking for a way to save Dean, so you helped by keeping him distracted. Once this was wrapped up, there was a witch in New Orleans you had your eye on who you hoped might be able to help.
The rest of the night passed without issue. It was actually relaxing just sitting and catching up with Dean.
You were up at the counter paying when Dean came up beside you, his arm snaking around your waist. “Thank you (y/n).”
“For what? It was my turn.”
Dean remained silent as you finished the transaction, his arm remaining around you. It stayed there as you made the walk back to the motel.
“I wasn't thanking you for dinner.”
“Cheapskate.” You teased.
You laughed, until you saw the look on his face. “What's wrong?” You asked, coming to a halt.
He stood in front of you, just watching you. Honestly, it was getting uncomfortable being scrutinized under his gaze.
“Thank you, for this. It's been a while since I've done anything like this. With Sammy, it's all about the deal and trying to save me.”
“Dean...”
“Let me finish (y/n).”
You did, not wanting to ruin the moment by telling him of your involvement.
“I know I have no right in asking you this, after everything that's happened, but...” He stopped short, running a hand over his face. He groaned before continuing. “Will you promise that once... once I'm gone, that you'll look after Sam and Bobby.”
“Dean, don't...”
“I know you'll take care of them (y/n).” Dean went on as if he didn't even hear you. “I-I just need to know they'll be in good hands.”
“This sounds too much like a goodbye.” You spat, hating the tears in your eyes.
Dean mustered a small smile. “Trust me sweetie, this isn't the goodbye I had intended for you. I just need to-”
“I promise.” You said quickly, not wanting to hear anything else in case you did start to cry.
Next thing you knew, his lips were on yours.
*End Flashback*

That night was engraved in your memory, especially the look on his face as he begged you to look after his little brother.
It should have been a blessing, instead it was a constant reminder of how you failed him.

Description
Dean was gone.
It was less than two weeks since that bitch Lilith collected on Dean's contract and had her dogs drag him to hell.
Two long agonizing weeks without your best friend.
You couldn't make it to his 'funeral', you had a nasty vengeful spirit you had to deal with in Reno. After that you went straight to Bobby's where you did nothing but drink and mourn with the old man.
Sam wasn't there, and he wouldn't answer his damn phone. For all you knew, he was lying dead in a ditch somewhere. Or caught in some vampires nest without back up. Maybe hung up in some nasty warehouse where a Dijin was feeding off him.
All the scenarios you come up with made you cringe.
Please don't be dead.
You took another swig of whatever you had found at Bobby's, it went down rough, but at this rate you didn't care, it did the job.
Feeling the warmth seep into your bones, you relaxed thinking about the last time you saw Dean. You had swore to him you'd look after Sam, and Bobby. So far you were doing a top notch job.

*Flashback*
You sat in a both at a local diner, laughing at Dean from across the table as he wiped the remnants of his dinner off his lap.
“It's not funny (nickname).”
And still you laughed, clutching at your sides that hurt.
“Laugh it up, you know what they say about payback.”
It was still another minute before you sobered. “Sorry, b-but you'd be the only one...” You were cut off as you broke out into another fit of laughter.
“Shut up.”
“Hey, at least it wasn't in baby.”
Dean paled at the mere thought.
You had met with the Winchester boys, investigating the same case.
You had a lead, but there was nothing you could do till the morning, so Dean suggested you go out and catch up since the last time you actually saw him was back at the Roadhouse months ago. Sam declined, wanting to do more research.
Little did Dean know is that you were helping in Sam's research project, and it wasn't on the case. No, you knew Sam was looking for a way to save Dean, so you helped by keeping him distracted. Once this was wrapped up, there was a witch in New Orleans you had your eye on who you hoped might be able to help.
The rest of the night passed without issue. It was actually relaxing just sitting and catching up with Dean.
You were up at the counter paying when Dean came up beside you, his arm snaking around your waist. “Thank you (y/n).”
“For what? It was my turn.”
Dean remained silent as you finished the transaction, his arm remaining around you. It stayed there as you made the walk back to the motel.
“I wasn't thanking you for dinner.”
“Cheapskate.” You teased.
You laughed, until you saw the look on his face. “What's wrong?” You asked, coming to a halt.
He stood in front of you, just watching you. Honestly, it was getting uncomfortable being scrutinized under his gaze.
“Thank you, for this. It's been a while since I've done anything like this. With Sammy, it's all about the deal and trying to save me.”
“Dean...”
“Let me finish (y/n).”
You did, not wanting to ruin the moment by telling him of your involvement.
“I know I have no right in asking you this, after everything that's happened, but...” He stopped short, running a hand over his face. He groaned before continuing. “Will you promise that once... once I'm gone, that you'll look after Sam and Bobby.”
“Dean, don't...”
“I know you'll take care of them (y/n).” Dean went on as if he didn't even hear you. “I-I just need to know they'll be in good hands.”
“This sounds too much like a goodbye.” You spat, hating the tears in your eyes.
Dean mustered a small smile. “Trust me sweetie, this isn't the goodbye I had intended for you. I just need to-”
“I promise.” You said quickly, not wanting to hear anything else in case you did start to cry.
Next thing you knew, his lips were on yours.
*End Flashback*

That night was engraved in your memory, especially the look on his face as he begged you to look after his little brother.
It should have been a blessing, instead it was a constant reminder of how you failed him.