I sure hope those are tears in Clark's eyes in panel 7 and not glass fragments. Hmm, who could this be? He doesn't look like Admiral Asshole Awesome. My other guess in the last panel was Brooder, but he might not be available here.
That definitely looks like tears, and I've got a suspicion that the chap we're looking at got foreshadowed back on page 106 (http://dudeindistress.thecomicseries.com/comics/135/#content-start), as well as a few comics leading up to that, and following, but 106 seems… pertinent.
Also, I'm pretty sure the location of the trouble mentioned on page 132 (http://dudeindistress.thecomicseries.com/comics/166/) reinforces my theory…
getting your nose broken often leads to severe watering of the eyes. Considering the way he was punched, and the amount of blood, I'd guess that's what happened.