He caught the mention of her mother, but he understood more than anyone that family members could be a hard subject, so he didn't push. It was oddly nice to know that they had something in common - even if it was someone to miss. "You went to a private school?" He asked, simply trying to understand. He realized then that he didn't know all too much about her beyond his own assumptions about how she acted and reacted around him.
"Company would be nice," he agreed. "But you've made a friend outta me, so you could always call on me if you need it." He hoped that he wasn't coming across as strong or overbearing. He just knew that, personally, sometimes he could use the company. He followed her into the elevator and gave her question serious thought. Obviously thinking of Sam caused him pain, but he didn't want to forget his brother, either.
"I honestly come and go about the peace and quiet." He shrugged, surprised by his honesty, but he continued with it. "I mean, don't get me wrong, a guy loves his privacy, but..." he loves his brother more "...that doesn't quite beat someone to talk to." And that was probably more honesty than he'd given someone that wasn't blood related in years. Dean Winchester. Full of layers.