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Like most people, two times a month I attend to online bill paying. This requires multiple attempts to sort incongruent accounting with a 1-800 number. The online amount due on portals is often not reconciled with the present amount due. American Express and utility companies are notoriously mysterious with debits and credits.
About a year ago I realized that being mad at a service representative ("please press #2") even if s/he barely speaks English or lives in a country across the world is not an advanced spiritual position. Now, however, we are faced with another growing obstacle.
Jill Lapore (American historian and journalist, b. 1966 -) in her essay, Bot or Not, which appeared on 8/17/26 in The New Yorker's "Brave New World Dept." column, gave her readers a test for determining if you are speaking with a human.
Ask: "Are You Wearing Socks?"

Human agents laugh or come up with a quirky way to answer this question that begins the tedious process of figuring how much I owe (based on what I've previously paid and what I've recently consumed). I'm asking for interpretations of statements issued by their employer that seems to require knowledge of Mandarin accounting. Of course most human service agents don't have the faintest idea. They are just trying to do their jobs with portals and platforms giving dead end decision trees, in accurate or incomplete information.They can only repeat what they see on their online dashboard even though often it doesn't reflect payments that have already been made.
I will mourn the day when I cannot dial 1-800 or 1-888 because I am of a generation when we could do that - pick up the phone and have the feeling that something was going to get done. Bills were going to get paid! Sorted for tax time!! Another task could be tackled and one could move on to another with a remote feeling of smug satisfaction. Some call it self esteem.
Newer generations who have grown up tied to cell phones as though they are a part of human anatomy often dread dialing the phone. For them this may mean having a conversation that cannot be scripted or edited and prefer texting chat bots or AI agents. For them, this is more natural and I suppose, they trust technology to solve their problems where I am suspect of it. So I suppose they are less angry? But it doesn't seem to work this way, either.
WHEN AI COULD NOT HELP ANSWER AN INARGUABLE SAFETY CONCERN
I did come up against it when a recent international flight was delayed for six hours and my driver could not do a 2 AM JFK airport pick up. I did not want to check into a NYC hotel if a reservation agent could not confirm that a concierge or bell hop would be at the front desk to let me during the dead of early morning.
Under the duress of a very delayed flight (thanks Jet Blue for the $75!), all I could imagine was standing with my new tan and suitcase on 59th/Park at 3 AM in the morning.
Way too late into a phone conversation attempting to make a room reservation with a corporate hotel chain on a 1-800 number, I realized that I was speaking with a service representative that could not admit to not being human. I hung up or clicked off, rather impolitely, realizing that the AI decision tree had not been coded to account for this question. Could I for sure be let into the hotel at 3 AM?
A human operator could have called the hotel that was ready to book the room and gotten the question answered quickly. I suppose this would have been a next step - presuming that some NYC hotels still employ human reservation agents.
HUMAN ENDING TO POTENTIALLY DANGEROUS SITUATION
It had not been necessary. Another human sitting next to me at the gate with her head in her hands (six hours is a long delay) had overheard my distress, even though I was trying to whisper with AI. It is a long time gone since I've lost it, either with
Imagine this. This fellow delayed passenger was also returning to the same state, in the same direction! Her driver could help us both!!
She was wearing socks.
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