He slowed his pace to a stop, making sure to leave a comfortable distance between them. There was no way to know if someone wanted to be part of a conversation or not until you initiated things. Well, unless they walked past you or turned tail and ran. At any rate, Rory was making a point of getting to know people, being friendly, putting himself out there as a possible assistant to anyone not taking to Red Oak well.
She managed to smile but she was out here, alone, probably a victim of insomnia or bad dreams like he was so he asked, "Hope everything's alright? Not to pry or anything, just that it's late and you looked a bit pensive. You're not new, are you? To Red Oak," he clarified. It was all of a second before he added with a slightly apologetic grin, "Sorry, that's a barrage of questions you probably weren't expecting. I've just been on the look out for arrivals to make sure they're not lost and that they get properly settled."