A/N: A great big thank you to those who took the time to read this story and an even bigger one to those who followed or faved it. Don't expect updates this often all the time but I can't get these plot bunnies out my head. This is set around 2 years before pilot but that might change as story develops. Please read and review. I'd love to know what you think even if it's negative. All mistakes are my own.

Disclaimer: Still not mine

Over the next few days I found myself making increasingly feeble excuses to call Dean. Not that I ever actually phoned him because, you know, I didn't actually know the guy but it was a close run thing. It was ridiculous. I had barely even spoken to the guy and now I was acting like a stereotypical teenager with her first crush. And I abhorred that sterotype. One time I actually had the cell in my hand with my finger on the dial button before I mentally shook myself and chucked it on my bed. What was wrong with me? I hadn't dared to ask Sam anymore questions about his family for fear of drawing suspicion upon myself even though he probably had been more suspicious that I wasn't asking question but whatever. I grew so stupidly paranoid that he's find out I had his brother's number I changed the name it was saved under to Winnie as a bit of a play on Winchester. I knew I was acting ridiculous but couldn't bring myself to stop. Finally, after all my obsessing, I found a legitimate excuse to phone Sam's mysterious brother and I had to stop myself from dancing with glee despite the reason I was calling. Sam had already asked me why I had a manically large grin present at all times. Yeah, wasn't really good at this whole subterfuge thing. I took a deep breath and dialled.

He picked up on the third ring. "Hello?" I frowned disapprovingly. His voice shouldn't be slurred mid-afternoon. Wait, was it mid-afternoon for him? Where did he even live? I internally cursed myself for being so judgemental.

"Erm, sorry, hi it's Jessica." I felt my face flush in embarrassment as I managed to trip over every word. Great first impression, Jess.

"Who?" The deep voice was even more gravelly drunk.

"Jessica Moore? Sam's girlfriend?" For some reason, I felt slightly disappointed that he hadn't remembered me. I mean, why should he? We've barely spoken let alone met.

"Is Sammy OK?". Disconcertingly, Dean now sounded almost completely sober. Who was this guy? And Sammy? Seriously?

"Yes, yes of course. Sam's fine. Well…" here I hesitated unsure of what to say now I was actually taking to Dean. I should of planned this a couple more times in my head. I plan everything. Apart from this. Not that Dean would've stuck to the script I mentally wrote for him so I guess planning was kinda pointless anyway. "Mostly fine. He's been drinking a bit today and been muttering about it being November 2nd?"

"Aw Sammy," Wait now he sounded relieved? Sam drinking was a relief? And again with the Sammy. Sam hated that nickname. All nicknames, actually. I'd always assumed that was just one of his pet peeves but now I wondered if it was because it reminded him of Dean. They'd obviously been close. It just made Dean all the more intriguing. And I love a mystery. Well, only mysteries I can solve. Otherwise they are just frustrating.

"So," I pressed, "I was wondering if you knew what was up."

"Hang on a minute. How did you get this number?" Dean was slurring subtly again but that was mainly hidden by the suspicion that laced his voice.

I winced. I was hoping that would not come up. "Um… well… I sorta copied it from Sam's cell… yeah sorry…" I spoke fast with long pauses. I prayed my tone didn't convey the mortification I felt but it probably did because I'm no actress.

"Oh." He gave none of his thoughts away. Unlike me.

"Anyway… November 2nd?" I repeated hopefull.

A rush of static that I deciphered as a sigh came through the line. "November 2nd." He murmured. "Well, November 2nd is kinda… the anniversary… the anniversary of our mom's death." The last few words came out in a hurried mess. Pain was evident in his voice. I was mortified beyond belief. I just had to bring that up. Well done, Jess. I silently berated myself.

"Shit. Oh god. I'm so stupid. I'm so so so sorry." My thoughts tumbled out my mouth. My mind whirled with this information. This was obviously why Dean was drunk. Who am I to judge? Oh God. I'm an idiot.

"It's fine. I just prefer not to talk about it." My guilt multiplied at the raw hurt still shining though his words. Great second conversation, Jess. "So yeah," he continued. "there's nothing really you can do for Sammy. He'll be fine tomorrow."

"I'm so sorry to bother you." A quick glance in the mirror revealed my face to be a prominent pink.

"I don't mind, darling. I'll always have time for you." He suddenly sounded charming. Slightly fake.

Wait… was he hitting on me? I felt slightly alarmed at the drastic change in tone. "OK? Thanks I guess. Bye?"

Like last time he hung up without warning. I sighed. My mind was churning with confusion, embarrassment and unanswered questions. However, he had said I could call him back. Well, OK, technically he said he always has time for me but that was basically the same thing, right? I smiled.

TBC…