1) Her name is likely spelled Eileen. That's how my middle name is spelled, and that's how the Irish band Dexy's Midnight Runners spelled it for Come On Eileen. Which I have had stuck in my head since last night.
2) "This surprises Dean, which is really odd, since he's expressed more than once that he doesn't expect to live a long life. Ah, continuity." - I didn't read it as Dean being surprised at the idea of them not living a long life so much as Dean being surprised (and concerned) because it was Sam saying it. Sam is always the one talking about being able to see a light at the end for both of them, and about finding love with someone who understands the lifestyle, and sunshiny sentiments like that. And here's Dean saying something Sam would normally be ecstatic to hear Dean say, and instead Sam is dolefully contradicting him instead. It dovetailed nicely into the graveyard scene after it with Dean checking in with Sam, and the bunker scene before it with Dean being concerned with Sam's post-Cage behavior – Dean investigating Sam's mental health and building a solid case for himself that something was wrong with his brother.
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Two thoughts:
1) Her name is likely spelled Eileen. That's how my middle name is spelled, and that's how the Irish band Dexy's Midnight Runners spelled it for Come On Eileen. Which I have had stuck in my head since last night.
2) "This surprises Dean, which is really odd, since he's expressed more than once that he doesn't expect to live a long life. Ah, continuity." - I didn't read it as Dean being surprised at the idea of them not living a long life so much as Dean being surprised (and concerned) because it was Sam saying it. Sam is always the one talking about being able to see a light at the end for both of them, and about finding love with someone who understands the lifestyle, and sunshiny sentiments like that. And here's Dean saying something Sam would normally be ecstatic to hear Dean say, and instead Sam is dolefully contradicting him instead. It dovetailed nicely into the graveyard scene after it with Dean checking in with Sam, and the bunker scene before it with Dean being concerned with Sam's post-Cage behavior – Dean investigating Sam's mental health and building a solid case for himself that something was wrong with his brother.