I see a lot of comments about the last few episodes that have some form of "that's so depressing!" in them. They're not necessarily complaints, some are witty, most are wailing and lamenting Dean's pain, but they all talk about how heavy the despair of our show is.
Supernatural is currently in stage 8 of the hero's journey as analyzed by Joseph Campbell and applied to modern storytelling by Christopher Vogler: The Ordeal. This is when all seems lost, when the hero confronts death, his greatest fear, or his most difficult choices. Dean, of course, is facing all three.
Sera Gamble has said Dean will hit rock bottom, and judging by the preview for tomorrow's episode, this is it. This is the moment in the fight scene where the hero is getting pummeled and suddenly finds the strength to turn the tide and fight back. But first, he has to give in to the pressure, the weight, he has to see what it's like to give up.
A number of things combined to bring Dean to this point, and I don't think he would have arrived here if any of them had been missing. First, Bobby seemed to give up. He didn't say the words, but it was clear that killing his wife again had at least temporarily broken his spirit, what little was left after he wound up in the wheelchair.
Then they die and go to heaven, and it's pile-on time. Dean confronts his losses* (Mary, Ash, Pamela, Jo and Ellen [obviously, the latter two not literally]) and gets the hard sell from Pamela about how heaven isn't so bad for those who die, and why not just let it happen**? At the same time, Sam's heaven sticks knife after knife into Dean's heart*** and God is just another deadbeat dad****.
Dean lost a lot all at once. By the time they got to Blue Earth, Minnesota, he'd been chewing on what he had left for a while. Beset by demons, facing one of Hell's horrors, seeing what it can do and knowing that the longer he and Sam hold out without destroying Lucifer, the worse things will get, it makes sense that he'd decide to end it the other way. The logic is there. If it's inevitable, if people can suffer for years this way and they can't ever win, why not speed it up?
Dean needs something to hold on to. Some reason to dig in his heels and resist. Could it be Lisa and Ben? Someone asked why it was Lisa and not Cassie. That's a good question, because he and Cassie had a lot more history than he and Lisa did. But his feelings for Cassie were young and immature. What he had with Lisa (not the bendy weekend, afterward) was all potential, but it was mature. It was who Dean is today, how he's been shaped over the last four years, what he wants for his future and believes he can't have. He and Lisa may or may not be meant for each other, but that's not really the point. Potential is the point.
Now, using them in a bargain isn't smart. Dean will be giving the enemy more ammunition. He can hold out when Bobby's paralyzed and Sam's got no lungs because they signed up for this gig, but Lisa and Ben are innocents. I doubt Dean's thinking of that—he's only thinking that he's got something the angels want, and if they want it, he wants something in return. Somewhere along the line, he'd better realize he can't trust any kind of bargain the angels agree to.
*Interesting that Dean sees Mary, at a time when John was not around, but never sees or considers that he will see John. I'm sure part of this is JDM's availability (or their desire to save him for the end, maybe? please?), but the writing is solid—Dean doesn't have many happy memories of John.
**Because Dean is humanity's champion, and life is not about dying, it's about living. People die every day without the apocalypse, but at least most of them get a chance, and sometimes a choice. Sure, many will wind up in heaven, but not all, and some of them will be coerced into going the other way (ref. Jane's murder of Paul last week). And before they get there, they might endure all the horrors Dean and Sam have fought so hard to defeat. He might have temporarily lost sight of that, in the relief of giving in, but it will galvanize him. I'm sure of it!
***Sam didn't really get a chance to explain, but he never saw his escapes as rejection of Dean. It will take a lot to convince Dean of that, and we might not get to see it (chick flick moments, you know), but somehow Sam will have to convince Dean that he's just as important to Sam as Sam is to him.
****I know the religion connection bothers a lot of people, but as an exploration of relationships, I LOVE this. Who doesn't ask how God could let horrible things happen? If humans are made in his image, why can't he be fallible, too? Why can't he also give in to despair and the relief of washing his hands of the problem? Ooooh, how would Dean feel to be told he and God have a lot in common?
The Rest of the Journey:
I have worked really hard...most of the time...to avoid spoilers. But today I couldn't resist and I clicked a link for promo photos of tomorrow night's episode, and saw...um...a spoiler. It made me mad! So of course, while I was writing this post, I went to IMDb to look at the summaries for past episodes, and read the writeup for next week. Which spoiled me again! I'm very excited, because it sounds like a super awesome episode and the specific spoiler makes me soooooo gleeful, but I wish I hadn't known.
Anyway, as sad as I am that we're down to 5 episodes remaining this season, I'm on the edge of my seat to see them:
Point of No Return
Hammer of the Gods
The Devil You Know
Two Minutes to Midnight