dumb questions to ask your best friend — and i have a working list

best friend is a strong word for somebody who owes me three hundred dollars from a transaction nobody documented. but dave qualifies. dumb questions to ask your best friend are not the same animal as dumb questions to ask anyone else, and i would like a tuesday morning to explain why.

writing this between two slack pings i have left on read. 4:47pm, the printer is making a noise i refuse to investigate, and the woman from procurement has been refilling her water bottle for fourteen minutes, which is not, technically, a meeting.

so. dumb questions to ask your best friend. there is a hierarchy nobody talks about, because most of the internet treats friendship like a flat field. it is not. friendship has tiers. the questions change at every tier.

dumb questions to ask your best friend: the small, useless, slightly cursed questions you would never put in front of a casual friend, because casual friends will think less of you. a best friend cannot. that is, structurally, what makes them a best friend.

CASUAL FRIENDS GET THE FILTERED QUESTIONS. BEST FRIEND GETS THE OTHERS.

last week’s dumb questions to ask friends, generally covered the regular tier. this is the upgrade.

the hierarchy, drawn from a desk reserved for spreadsheets

tier zero: strangers and coworkers. weather, train, whether the coffee is fresh. sounds, not questions.

tier one: acquaintances and group-chat people. the show everybody is watching. you cannot ask whether bread is a kind of cake here. i have been removed from a group chat. fine, i deserved it.

tier two: regular friends. pasta shapes, the moon, is silence a sound. friend laughs, friend plays along, friend, after eight minutes, finds an excuse and hangs up.

tier three: the best friend. different physics. longer, uglier, about money, about death, about the things you do alone in your kitchen at 11pm. the best friend does not hang up. that is what you bought, with fifteen years of small loans and one undocumented three-hundred-dollar transaction we are not discussing.

what makes a best-friend question structurally different

regular dumb questions are about the world. the world is the topic, friendship is the medium. dumb questions to ask your best friend invert that. friendship becomes the topic. the world is the medium. you bring up an object only because you want to know something about each other you cannot just ask.

regular tier: “is silence a sound.” best-friend tier: “if i died on a wednesday, would you tell my mother in person, or let it be a phone call, and be honest because i need to plan around it.” both are stupid. only one gets asked between two people who have, between them, one functional kitchen.

six examples, fresh, from a transcript dave does not know i keep

i went through the call log. wrote them on the back of a printout from a meeting i did not attend. tier three.

1. “if my apartment caught fire and i could only grab one thing, would you judge me, in writing, after the fact, for what i picked.” dave: yes. and he would publish it. i believed him.
2. “do you think the fact that i still own three yoga mats and have used them, between them, twice, is a personality flaw or a financial one.” dave: financial, the third one was on sale. it is both.
3. “if i never paid you back the thing i owe you, would the friendship survive, or would something quiet break, and we wouldn’t notice for a year.” long pause. dave said “we’d notice.” gently. we did not continue.
4. “if i told you i had not opened my mail in seven weeks, would you, as a man in insurance, have to say something, or as a friend let it slide.” dave: he would say something. then let it slide. then say it again.
5. “would you attend my funeral if it were on a tuesday during your fantasy football draft.” dave: yes. drafting from the parking lot. completely sure. i was moved, and refused to admit it.
6. “if my mother called you because she could not reach me, would you cover, or tell her the truth.” dave: cover, but only once per quarter. dave has a policy. i did not know he had a policy. i was honoured.

mom, wednesday, and the question i did not ask dave

mom called wednesday at 4:11pm — “after my walk and before the news”. i let it ring twice. i picked up on the third because she counts.

she asked how i was. i said fine. she said “why does fine sound smaller than usual.” i said it didn’t. then she asked whether i had any savings. i said yes. she said how much. i lied — a number that sounded like a number. she did not raise the volume. that is mom’s technique. she lets the lie sit there until i hear it, with her, in the silence. five seconds. ten. fifteen. i broke. i told her the real number.

mom said one thing, kindly, and hung up: “savings accounts are a hobby for the wealthy, sweetheart.” she meant it as fact, the way she explains the weather. savings accounts ARE a hobby for the wealthy. the rest of us have a slower checking account with extra steps.

i did not call dave after that. picked up the phone. put it down. that question was not tier three. it was tier four, and tier four does not exist yet. some questions only get asked of yourself, in the kitchen, with one AirPod in (the other gave up in 2022; binaural is a luxury i no longer afford), at the volume of nobody.

why dave gets them and tom does not

tom, from university, owns a house, a wife, two children, and a pension he understands. tom and i exchange a text on birthdays. tier one. i can ask tom whether he saw the game. i cannot ask tom whether i should open my mail.

dave has, in fifteen years, never once told me to grow up. that is the whole resume. tom would offer a side-by-side comparison of our retirement accounts. dave would say “open three of them, hold the rest, see if anything blinks.” dave’s wrong is in my dialect. tom’s right is in another language i used to speak.

dave has a weekly check-in he pretends is accidental. on his calendar it is a recurring event called “the idiot, weekly.” dave thinks i don’t know. i’m not going to tell him. that is also tier three. you protect each other from things you accidentally found out.

how to know if you have a best friend

sample size of one (dave). here is what i have noticed. you have a best friend if:

• you can ask them a question containing the word “money” and they do not change the subject.
• you can call after 9pm without an apology in the first sentence.
• you describe a dumb thing you did and they ask follow-up questions instead of looking concerned.
• they have lent you money and not asked for it back, but also not pretended they didn’t.
• your mother knows their name and asks about them, by name, on wednesday.

mom asks about dave by name. mom does not ask about tom. she knew dave would be the long contract before i did. mothers know. it is their power.

if your tier three is empty, i would not panic. more common than the wellness people will tell you. the broader case for dumb as a working philosophy is the pillar this hangs from. there is also the manifesto on dumb and dumber, and the working hierarchy of myself. and the 1994 road movie i will not name is, mechanically, two and a half hours of one man asking another tier-three questions in a dog-shaped van.

the printer has stopped. procurement has refilled the bottle a fifteenth time. twenty-two minutes before someone notices the spreadsheet has not moved.

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