(1/2)
Dean wasn't used to people being able to read him that well and from the Captain's look the hunter didn't seem to be that interesting of a story. Then again after the bulk of what the other man told him next Dean supposed things didn't get more interesting than one Captain Jack Harkness. After the subject of time travel was put on the table Dean decided that the glass of scotch that had been pushed in his way was the prettiest thing he'd seen all day, even when compared to the inquisitive baby blues still staring in his direction silently waiting for the hunter to reciprocate and put his cards on the table. Cause that was the only way he'd be getting any help here and as much as Dean hated to admit that he needed it, well he didn't really have a choice at this point.
After a short pull, an annoying habit he'd been forced to pick up because luxuries like good liquor were hard to come by post-apocalypse, just enough to feel the beginning of a burn at the back of his throat, Dean tilted his head from side to side, cracking some of the tension from his neck as he mentally prepared himself. To answer any of the other man's questions, both stated and not-so-subtly implied, Dean was going to have dig deep into that mental black box of batshit crazy he rarely acknowledged in the light of day, filled with dark unmentionable things that no normal human was ever meant to experience let alone live through. Luckily, or maybe not depending on who you asked, Dean had a pretty good penchant for living when logic and ultimately fate was against him and he was putting a lot on the line now with the plan that was rattling in his head that his track record would stick.
Still to even get that far first, as the Captain so neatly put it, he'd have to explain himself and that was going to be so many bucket loads full of fun he could hardly stand it. Ah, sarcasm. How Dean has missed his lifelong friend. Now amused at his own somewhat lame mental joke, lips quirking up into an easy smirk, Dean figured it was as good a time as any to rip off the band aid and get this over with. "Well if we're starting this off how many times we've died then I've got three times here under my belt. And then something over hundred in another place. Some kind of pocket dimension conjured up by a runaway archangel playing at being a demigod trickster. He had a pretty sadistic sense of humor."
Considering this was the first time he'd ever admitted out loud to anyone about remembering the numerous deaths that had been thrust upon on him during the time he and his brother had been trapped in that damn mystery spot, time loop from hell fiasco Dean thought he deserved another drink for that. Taking a second short pull from his glass, damn his brain, and fuck all of what Jack might interpret from it. Because Dean and the concept of 'opening up to another person' was rarely ever a pretty sight for anyone involved. But he'd never shied away from doing what he needed to do just because it was difficult in the past. So he took a breath and relaxed further back into his chair, lifting one leg to rest his ankle on the opposite knee, fingers idly curled around the top of his glass as he took a moment before he looked back up at Jack and continued, "Twenty-fifth century huh? Considering the way things are now I didn't think we'd make it that far, but I guess whatever happens here to us doesn't really stop time from moving on, does it?"