I’d argue that today’s strip is the product of an AI tasked with generating images for the word “wistful”… but that’s an insult to artificial intelligence and I don’t want to be responsible for unleashing Skynet. This is just completely sad, but in the stupidest way.
Mindy is the one that really punches up the stupidity here. First, “when” Ruby retires is essentially right now, it doesn’t need to be discussed as if it is well in the future. Second, Mindy also draws a paycheck from Atomik Komix… so does she dramatically underestimate the financial resources it takes to travel extensively or does Chester really pay that well?
And if Chester pays that well, why can’t he spend some money on an office that doesn’t look like a dungeon crawl game being played on a vintage grayscale Macintosh? Maybe everything in the office is made of stone. So that’s why they called him “Chester the Chiseler”!