See, this is what happens when you half-ass it.
Tom Batiuk had this hilarious joke about how only old people use the post office, but he lost that joke somewhere on his desk, so we got this one instead:

Because it might have been “okay” if the length of time was a week, or a month, but if it was a year? Man, the laughs just don’t stop. Mainly because they never start.
The problem seeps in when we look at what he wrote on the 31st of July.

So, the “always like” seems to imply that he’s done this more than once. But the “this year” above seems to imply that he only does it once a year or so.
Which means that Jessica is still in Los Angeles, while Dullard has been in Cleveland for a year.
Or, what I think is more likely, Jessica has jettisoned his sorry ass and is living a successful life elsewhere, and Dullard just likes to “pretend” he has a relationship.
Either way, it makes Dullard look bad, so thumbs up from me!
PS: Speaking of artwork, it almost looks like Commissioner Gordon from the Tim Burton Batman movies checking his watch, and is that Chuck Ayers himself in the beard?