Chuck did not have any hang ups with the offer of Dean offering to look out for him. Maybe he should be more cautious - he was, essentially, the first adult he ever met that he remembered. But Dean was giving them food and seemed really nice, so that shouldn't be a problem, right?
"Thanks, Dean!" Chuck could be somewhat self-sufficient thanks to the Maze, but he was still just a kid. The offer seemed to put him more at ease. "I like meat." He wasn't really fussy though. Surviving on whatever you had meant you weren't picky. As if to demonstrate the point, Chuck took a big bite of sausage that he picked up with his hand. "You're really good at cooking too. This all tastes so good"