So I think Kevin was actually hallucinating. I wasn't sure, but when Sam and Dean came in I was checking the windows and they were intact and there was no broken glass anywhere. I don't think demons have a magic window-fixing power...even Crowley.
So I thought they had killed Mrs. Tran in one line, but if it was all in Kevin's head she is still alive. He must be having a psychotic break...
When Dean brought in food I thought I saw a piece of pie and thought "Dean will finally get some pie!" But of course Kevin stole it! And Dean plaintively said that was his pie (confirming that it was pie to me!)...Poor Dean never (only once?) gets his pie.
I am pretty upset about how easy it was for Sam and Dean to find a way into Hell. All that time Sam searched for a way to save Dean from Hell (and later Dean searching for a way to save Sam) and they didn't find out reapers could get them in? And they've tortured demons for info before! Maybe this particular demon was weak or the boys have gotten to be better torturers (though it only looked like they used holy water this time)...but I don't buy it. It was all too easy. It was a cool idea, but they needed a better way for the guys to find out about it.
Also, season 6 was all about getting to purgatory! And this reaper got in so easily--and Crowley knows him and the guy works for Crowley...It's just not consistant.
Also, time passes differently in Hell, so that 24 hour limit and Sam's watch matching up is fishy. And just how quickly Sam finds Bobby in the vastness that is Hell, and Benny finds them in purgatory (when he and Dean spent months/weeks looking for Cas), and Dean finds Sam in the vastness that is a 100-mile-stretch-of-forest-in-Maine...
But I did like how things got complicated later on. Naomi is trying to win Dean's trust and I don't think he's buying it. But they know now she could be a useful but dangerous source...though they could never trust her.
That reaper wasn't a good liar at first, but then he improved and didn't spill that Sam was already in Hell or that he was going after Bobby. [Not sure what Crowley's scene with the secretary!demon was for--to show us he realizes something is up I guess?]
Also I loved that Dean reconnected with Benny. As soon as he did I realized they were going to kill Benny to get Sam out of purgatory. Benny and Dean's scene was very emotional. I was really getting close vibes from them. Dean teared up quite a few times this episode--this scene and later when Sam gets out safe. And we got a brother hug! (Plus Dean hugged Benny too.)
I like that they didn't show Benny's death--it was mostly off screen. That was a nice touch.
So I wasn't surprised it was Bobby rescued from Hell, but I'm still sad they didn't use Adam. Poor forgotten Adam...
Bobby even mentions how off it was for Sam not to look for Dean! Something more has to be going on than we've been shown! I will hope out hope until the season is over!
Overall I'd say okay episode.
And it looks like 2 weeks until the next new episode? But it looks cool! Dean will be in a hot uniform.