Wisdom of the Ages, a segment about analyzing common cultural wisdom, makes its return in this pain-themed episode. Bennett has Daniel analyze common sayings that have something to do with pain, and in the process, they ask many thought-provoking questions. What are the differences between physical and mental pain? What is the value of loyalty, and when is it okay to break confidentiality? Is it possible to "pause time" and never allow pain to heal? All of this from common, trite sayings. But that's the point of the segment: to reexamine wisdom that might be taken for granted.

How do people who wear glasses manage it? That is what Bennett asks after getting his first pair in over 25 years. Warping, shrinking, and chromatic aberration... why not just get contacts?! Bennett and Daniel discuss, and then a long dormant segments returns, just in the nick of time: Bennett Fixes Sports. Bennett, a known fan, and some might say expert, analyzes the pros and cons of football and then suggests a number of improvements to make this fading sport truly stand the test of time.

Turnabout is fair play, and in this episode, Bennett avenges himself on Daniel for past gotchas. Daniel has in the past sprung a segment called "Father Bennett" on Bennett, where he puts Bennett in the hypothetical role of a father and asks uncomfortable parenting questions. Bennett turns the tables and asks Daniel, now and actual father of two year old Cosmo, how he would handle situations such as potentially embarrassing high school choices, aesthetic decisions, and technological methods of disobedience.

In this aging-themed podcast, Bennett and Daniel muse on the adventure of getting older, beginning with a vaguely age-themed Adventures in Etymology. Next, they discuss retirement; what is the purpose of retirement? What are its benefits and drawbacks, and what would happen if we retired in the middle of our lives instead of at the end?

Bennett gives an 18 year out-of-date review of No Country for Old men, criticizing its postmodern qualities, and then Bennett and Daniel discuss surveillance. With the ever-present increase in technological sophistication and affordability, cameras are ubiquitous: doorbells, bodycams, traffic cameras, and more. Is this a good thing? Why do we value privacy? Is security worth it? What about cameras in the workplace, like in the classroom or in a technical field? The pros and cons are weighed, and Daniel and Bennett give their views (audio only, of course).

Daniel and Bennett discuss the Independence Day fireworks hangover, Costco evangelism, and penny pinching before diving headlong into a long-awaited Superpowers and Drawbacks. This time, they consider the benefits of salvaged food weighed carefully against hirsute bedspreads.

Bennett introduces a new segment called Wisdom of the Ages, in which he takes three common aphorisms that everyone knows and has Daniel assess the wisdom contained in them. How should we treat so-called enemies? How is it that people with seemingly incompatible characteristics end up together? Should one gravitate toward or reject stereotypes? All of these are examined, and Daniel also talks a little about the new house he's buying.

Bennett discusses the difficulty of digging holes, and then perhaps digs a metaphorical hole with this episode's spicy (or zesty?) Mind Your Morals, which focuses on homosexuality. What if a substance were invented that could eliminate the same-sex attraction and restore opposite-sex attraction? Bennett quizzes Daniel on multiple scenarios of this hypothetical drug's use to see what the moral implications of such an invention might be.