Hey there, nice to see another Chicagoan on the boards.
I watched your short (without sound, so this is just a visual critique). What was with all the shots of the brands and labels all front and center? Was this supposed to be an ad or something? I see the characters talking about the stuff, but I still think it's kind of weird to be advertising the jewel brand of all things....
You obviously have a nice camera, a lot of the shots look great. Nice camera work on the skating sequence. What kind of stabilizer do you use? I might have liked to see some color correction on those shots, it was all very white and bland (the sky being overcast doesn't help, I'd love to see some blue brought out there). This could partially be avoided by having your actors wear clothes that stand out a bit more from the background.
I know I was watching it with no sound, but I think those long dialogue shots would flow better if you threw in some over the shoulder shots and cut it tighter(you actually could cut the whole thing a lot more tightly, this would be better if it were 3-4min shorter, and I don't mean that in an insulting way). You seem to have some grasp of DOF, so that would make an over the shoulder shot look great.