Which is exactly why he knows he should have come to Dean sooner. If there's any other idea more effective than to jailbreak heaven without a clue of how to find Ruby, he's all for listening.

Honestly, that's exactly how Sam expects Dean to react. It's not the worst reaction he's ever received by far, but the disappointment (as he perceives it) is palpable. He drops his shoulders. He turns his eyes down long before Dean is able to speak. "I know what I did. I'm not making excuses for that. Ruby knows because I... I wrote to her because I couldn't lie about something so big. I wrote to her many times."