This (well, this especially, but the last few as well) have been classic Achewood for me. It's funny, and then when you get to the punchline (the funny part) there's something else there. Funny, but also scary or depressing, possibly one quality because of the other. Classic "glass eye in the gumball machine" sorta stuff. I guess that's what keeps me coming back.
Honestly, though, if you don't find the punchline funny (or disturbingly familiar), you haven't spent enough time meeting people in the context of trying to play an online game. Sometimes you get a nice round of checkers, but more often you get a larger than recommended dose of the personal life of somebody who only socializes via internet checkers (while wearing a brass diving helmet).
It's a little better with more complicated games... The people there have invested a lot in the ability to beat up imaginary monsters for their lunch money or what have you, and are more likely to actually go about doing that, but often you still learn something about someone that you'd rather you hadn't. It is sometimes like overhearing the locker room conversations of people who are afraid to leave their houses, with orcs and a Howard Shore soundtrack.