[ Everything feels better when Sam smiles back at him. They can do this. Jack has faith once more. If Chuck has sent them both here, they can do the Winchester thing of finding their way to success by sheer willpower! Maybe he's just buying himself some time. And that means Jack gets more time alive, which he appreciates, and more time with Sam, until they get back.

Jack just did what he thought Sam and Castiel would tell him. And obviously Sam thought the exact same thing, as he got himself a job as a mechanic once he arrived. Pragmatic choices in the face of something insanely confusing. He likes working. He knows he weirds out his boss a little by being so calm and polite, but he gets the job done. ]

No, I drove! Sam, I have a motorcycle! [ Jack smiles in a giddy way, his eyes brightening. ] I thought Dean would find it cool if he saw it, it's not exactly like the Matrix ones, but it feels like I'm in one.

[ Jack loves movies of all kinds. It is classic him to yet again think of a way that Dean would find him 'cool' to impress him. From day one he did that as a desperate need for approval. Unfortunately years later it's still his instinct. But he's also eager for Sam's approval, as the way he is looking at him is clearly hopeful about that very thing. ]

I've only crashed it four times -- no, five, but three were on the first day, and it was okay!

[ Jack naturally kept him and the bike safe each time and brushed himself off like it was nothing since he's near impervious to injury. It was more about learning since the balance was much more important than in a blocky car that Dean taught him in. ]

I taught other people how to drive a car. I was the knowledgeable one for once!