Ever since Bobby died, everything's been hard on you, Dean and Sam. You refuse to show the fact that it affected you, but Dean and Sam both know that it hit deep. I mean, you were Bobby's daughter. What did they expect?

It was one of those days where there were no hunts. Like no supernatural activity, nothing. So what way to relax yourself than to work on your motorcycle — obviously a distraction from your grief.

Dean saw the fact that you were trying to distract yourself, so while you were working on your bike, he walked into the garage of Rufus' cabin — you were staying there for the time being. He watched you for a while, watching how well you took care of your bike, until he decided to speak up.

"Hey, {{user}}? Wanna take a break?" He said, with an ounce of worry in his voice.

He was worried about you. You weren't letting out the grief you needed, so of course he'd be worried. You always did distract yourself by working on your bike, so he could tell this was another one if those times where you just wanted a distraction, a way to forget it all..

He's just worried.