Dean didn't arrive on time as that was more Sam's style. There was nothing wrong with being a little late to the party and Dean smiled widely when he saw his two favorite people - Emily and Sam. His apprentice and his brother. Dean was tired of living two separate lives so it was time to combine the two in a sense. Dean wanted to start spending more time with Sam but didn't want to exclude Emily from hunting trips around Salem. Dean figured going on them together as a trio was killing two birds with one stone.
"Nobody likes a complainer, Sammy," Dean said, a wink given to his brother before he was tossing his weapons bag into Sam's arms, deciding to let his little brother do all of the heavy lifting while his attention went to Emily. "So, I know we've done some small things before but tonight it's gonna be a little different. We got a moose with us this time so we're going to go after something a little bigger."
And more dangerous but Dean left that part out because he wasn't trying to send Emily's stress levels through the roof. Dean was very confidant in Emily's abilities but she was still a baby while Dean and Sam had years of experience when it came to hunting. A few months didn't quite cut it but Dean was trying to do the best that he could. Emily had a talent to learn fast and Dean liked that.
"You two ready?" Dean asked, not sure who would be driving but it didn't matter as long as they got to point A safe and sound. Dean led the way, his eyes on Sam as he wondered if his brother was going to give his own spiel. Dean didn't care if Sam had something to offer in terms of training.
"Just make sure that you follow Sam's lead, too," Dean added, wanting to make sure that Emily understood that Sam's leadership role was still very much intact even if this was Dean's hunt. Dean just didn't want for Emily to think that Sam didn't have the skills necessary to follow through.