The fact that Cas isn’t actually in “It’s a Terrible Life” as Dean’s hot secretary is a friggin travesty.
Actually, I’ve thought about this A LOT, and while Cas’s absence in the terrible life!verse is a total travesty, look at what we do see in this episode.
Health club quips aside, we actually don’t see Dean flirting with a single woman in this episode. In fact, we barely see Dean talking to anyone who isn’t Zachariah or Sam in this episode. The only time we don’t see Dean with Zach or Sam…Dean’s talking to this guy.
Who is this guy, anyway? No idea. But just look at this dude. Dark hair. Dark suit. Blue tie. Remind you of anyone? And what is Dean talking about with this guy? …Project Runway. I can’t help but think of the appearance of this actor as anything but intentional.
Look at what doesn’t happen in this episode. You know what I might have expected to see in an episode where our Dean Winchester finds himself in an office environment? For him to flirt outrageously with a hot female secretary. (Especially if the episode was written by, say, Robert Singer.) But this Dean doesn’t flirt with any Hot Female Secretaries. In fact, there doesn’t seem to be any Hot Female Secretaries in the building for him to flirt with. Or at least, he’s not going out of his way in order to find them.
There’s a glaringly noticeable lack of Hot Female Secretary in this episode, actually. I mean, if there had been a hot female secretary, we would have expected Dean to flirt with her, wouldn’t we? Because our Dean likes to flirt with hot young women, right? It almost seems strange that a Dean-flirting-with-the-sexy-secretary scene wasn’t written in this episode. But then, this is a Sera Gamble episode.
Because..what if there had been a Hot Female Secretary - and Dean didn’t flirt with her? What would that have made us think about Dean Smith? Dean Winchester, according to John Winchester’s journal, is a ladies’ man. But Dean Smith, who was never raised by John, might not feel like he has to flirt with women in order to feel powerful, competent, secure with himself. And Dean Smith is clearly all of these things.
Sera Gamble has a bad rep in fandom, but she’s actually a wonderful writer and something of a genius. She probably couldn’t have managed to work Castiel into this episode, and certainly she couldn’t have written a scene where Dean flirts unknowingly with Castiel as his secretary. But she gives us the next best thing - a Castiel look-alike, to whom Dean interacts with in a very friendly manner.
I think the point is (if there is even a point here to make, I’m really just rambling) that Dean tends to express more aspects of his genuine personality around other men than he does around women, with whom he feels compelled to put up a front of masculinity. Dean lets himself go around men. He tends to put on a show for women.
I will maintain that “It’s a Terrible Life” really gives us an incredible insight into Dean’s personality. By seeing Dean Smith juxtaposed against the Dean Winchester we’ve known for four seasons, and seeing various aspects of Dean Smith highlighted in this episode that we hadn’t previously seen expressed so obviously by Dean Winchester - thoroughly enjoying his crappy tv shows, a penchant for dressing up, worrying over his appearance - we get a pretty good sense of what aspects of Dean’s personality might have been influenced by being parented by John and what aspects are just the Genuine Dean. Nature vs. nurture, you know.
casually scrolling through my dash and DO YOU REALIZE WHO THAT GUY IS THAT DEAN IS TALKING TO??!
it’s the guy from “conversations with my 2 year old” on youtube!! what!!