Jerome wasn't able to really figure out what Tobias' slight reluctance was about, but as it was subtle and not horribly apparent, he hoped that Tobias would just need a little bit of time to warm up to a stranger, opposed to being dragged into a search he didn't really want participate in. No matter how urgent and necessary this search was, by now, Jerome knew perfectly well that the things happening around here fucked with people's brains, and he sure as hell didn't want to expose people to things they were uncomfortable with. If things needed to be done, there were enough people willing to do it, and unless everyone had to participate in some stupid event, nobody needed to be burdened with more responsibility than they could bear.
He was probably overthinking things, and someone else maybe wouldn't even have noticed Tobias' hesistance, but as he was used to always trying to read the mood of his daughter, trying to help whenever she felt anxious or depressed, always fearing for her well-being even in the most relaxed of situations, his mind basically forced those things into his consciousness when he encountered them elsewhere, triggering sympathy on the spot.
"Well, I hope I still am." A tiny laugh fled his lips, covering up the slight uncomfortableness accompanying the thought of not being able to return to his job anytime soon. His life. His family. A downward spiral of thoughts he surely wouldn't enter now, but speaking about his life in the past tense wasn't especially comforting. Not that he would hold that against Tobias in any way, nodding along to the things he added to his initial question.
"That's convenient. I only know where those places are because I saw them on the map, I've never been there before. Your first-hand knowledge could really help." He smiled again, wondering how long Tobias was already here, and why the hell he had been inside a building Oliver had told him was basically a ruin he shouldn't enter, but those questions, if at all, were something for later. He finished up his own mug, putting it inside the backpack which was already situated on a nearby chair along with this nasty winter gear he hated so much. Presumable American winters were fucking awful.