If they had to share John's car when finding him again, she may have been a bit more hesitant at following Dean back into the field metaphorically speaking, but the fact she had her own car, it meant her and Dean could find John and stay in her car, taking turns to drive and reduce the amount of conflicts as possible. Yet when they did have to share John's impala, then they would but she hoped that would be rare in comparison. She smirked at him calling her like Sammy in the regard of butting heads with John but she also saw the brief moment of sadness in his face when he brought up his baby brother once more. She followed his movements with her eyes only as he tapped the glass down on the bar for another drink. Seeing the signal Jess gave she gave her a silent nod in thanks for her making the signal that Dean shouldn't have another drink after this one she just poured him. There had been so many times when she wanted to ask Dean the question she finally asked, but until now she didn't see a valid reason for asking it. Hells, she didn't want to ask it now but she knew if she was to be around John then she had to know what persona he knew her as so she knew what she was going to be walking into. She was also convinced Bobby wouldn't be best pleased with her going off with Dean and being around John so much. So she listened to his answer when he plucked up the inner strength to give her it, nodding in understanding. She knew John wasn't ever her biggest fan, but there were times when she thought he sort of liked her because she wasn't like the other girls he used to go around with. Hearing that wasn't the case made her realise that the Chambers/Winchester/Singer family fued triangle clearly went deeper than either her or Dean truly realised. Yet the slither of hope she did get out of his words was that she was his reason early on to want out of the hunter's life and actually settle down. She squeezed his hand that was still on his lap, leaning forward and kissing him softly and briefly before pulling away, "hey.. Listen to me Dean Winchester. You are NEVER going to go through anything alone again with me around. We're a team. We have defied so many odds to be together again and I won't let you do anything alone, just like you won't let me do anything alone. You and me? We're forever. We're home. No matter what." she told him with strong conviction. Sure, they have their issues and they fight, have angry sex to make up with each other and so forth but at the end of it all they were solid and too stubborn to let each other break up for long. "I love you Dean. If sitting down and talking with your dad is what it takes to be with you then I'll do it. But first we gotta convince dear ol' Uncle Bobby" she told him, ending it on a slightly more lighthearted tone.