John Wilson reflects on the delicate balancing act of making – and safely redirecting – casual conversation, highlighting the rewards and risks of small talk.

After realizing too much of his life is spent inside, John tries out birding, which opens up a world of possibility...and dubious claims.

John Wilson offers a unique history of New York’s hideous yet sprawling network of overhead “protection,” otherwise known as scaffolding – and contemplates what it might take to reduce its nearly 300-mile eyesore presently overtaking the city.

John Wilson taps into his “Memory Palace” for an unforgettable exploration into our ability – or inability – to remember things.

John Wilson attempts to make sense of the intricacies – and fairness practices – behind the complex art of splitting the check.

After having his ears properly cleaned, John wonders if better hearing is what he actually wants.

John reflects on the competitive and complex process of parking in NYC, where the possibilities opened by having a car comes with a catch.

Seeking a solution to the universal conundrum of battery disposal, John ponders the value of things we hold onto – and what we throw away.

As the availability of public restrooms dwindles in NYC, John tries to find clever ways to relieve himself.

After renting the same apartment for years, John contemplates an unexpected opportunity to become a homeowner.

After years of rooting his life in non-fiction, John drifts from the world of rational thought in hopes of finally remembering his dreams.

Though determined to let fate be his guide, John’s attempt at spontaneity doesn’t go as planned.

While trying to live peacefully with his furniture destroying cat, John Wilson explores the challenges of keeping an object in pristine condition.

When confronted by the overwhelming and mysterious world of wine, John attempts to master his senses and make informed choices.

John starts working out and tracks the pros and cons of big.

John's discovery of the deeply-embedded rituals and bonding in sports leads to a greater appreciation of the game.

After having a delivery stolen, John investigates how to keep his packages secure.

To thank his elderly landlord for all the times she has cooked and cleaned for him, John attempts to make her favorite dish. Season finale.