Last night, playing with photoshop to try and wake Poet up... I was looking for decent callum-spam. This is irrelevent...
More relevent, is Newbie's shirts. Think of Newbie's shirts. Then think about Sandor in Asylum. Make a little photo line-up and you have the totally valid point --
Newbie!Callum dresses like Poet!Callum and his best friend Sandor, secret member of the bongo underground* and clearly Ray's guide to the "alternative" Chicago after the break up with Stella (yes, he could have been having it off before then, but Ray just isn't that guy, he's the obsessed and consumed guy) and - yeah - maybe sex on the side, just good-times not lifetimes. That's why there is Tony, king of pizza.
*he's a drum player and he hears about everything, like why the drummer in Jenifur is having a bad time of things... and there's this dead punk following the band around (or so the drummer says).