I don't think there's a scene with Bobby that I don't like, but the scene where Dean tells Bobby about his deal to save Sam, and Bobby's obvious distress at it, is an amazing scene.
I also think the whole episode, Weekend at Bobby's' is just delightful!
Day 14 - Ruby 1.0 or Ruby 2.0
I don't really have a preference one way or the other, so I'm going to say Ruby 2.0 as Gen is now a much-loved member of the Spn family.
Day 15 - Episode that makes you cry
A Very Supernatural Christmas is one of those great bittersweet episodes that has you laughing uproariously and then sobbing within just a few minutes. Also< on the subject of Bobby, the seasn 7 episodes, Death's Door, where we lose Bobby is a feal tearjerker too!