I was thinking I missed something too, when I first heard Nate make the chaperone comment. After a second viewing, I just thought maybe Nate was saying it was the first time he and Ray had been alone together, at least until Nick showed up and Nate said something like "No fair". During the video portion of the class, there were all the students, and then while Nate was in custody helping on the Jekyll case, there was always a guard present. Of course, I can't be sure though. Another question. I thought Ray was from back east, or did I get that wrong? I remember him saying his first date was with Gloria in Baltimore, but I guess that could have just been where he went to Med School.