The Guideposts Advice Column
your most bizarre personal conundrums answered
Every publication worth its salt has an advice column, allowing readers to receive sage wisdom from erudite authors, but so many of these advice columns take the easy route: simple scenarios with pat answers. This is boring, and me and my very talented and very funny collaborator Grace Leuenberger are not about that noise.
Grace and I have also noticed a worrying trend where people trust AI chatbots to give them personal life advice, instead of turning to the people who actually know and love them — the kind of people who would take the time to write a handwritten letter and fold it into an envelope and lick the stamp and send it via the postage system.
So Grace and I decided to change up the advice game a little, by restricting ourselves to a few rules:
We would only accept people’s most unhinged, metaphysically unstable personal conundrums.1
We would both assume the mantle of a set character. Grace would write her answers as ‘Snail Mail’ and I would write as ‘AI’.2
We would provide a poll under each set of answers so readers could tell us which they preferred: Snail Mail or AI?
So with no further ado, Waymarkers is proud to present, The Guideposts Advice Column: Snail Mail vs AI edition.
Dear Guideposts,
Last summer I had coffee with a member of the Air Force, and now I hear every single airplane or helicopter that flies over my house (and perhaps even a few that don’t). At one point last summer I also saw a B-2 fly by overhead, so I now feel compelled, upon hearing a plane, to search the skies until I spot it. As yet I’ve felt no negative effects, other than the odd dream of air shows and an increased risk of tripping on the sidewalk while looking heavenward, but neither do I especially want to hear every plane in close range for the rest of my life. What would you advise?
Sincerely,
Keen-eared in flyover country
Dear Keen-eared,
I’ll come right out and say it: this is just plane baffling. As I consider this conundrum, I have two possibilities I want to explore with you.
The first is a fairly straightforward suggestion that what you are experiencing is a relatively harmless and common experience with the ‘Baader-Meinhof Phenomenon’, a cognitive bias that affects perception of the frequency of objects, words or events. Since your coffee date (I’ll call him Air Force Aaron), is a professional plane person, it sounds like you may be newly and particularly attuned to the presence of aircraft in your area. Could it be that ever since Air Force Aaron ordered that Americano in his tailored uniform (hot) and mentioned his training in jumping out of helicopters with a parachute (also hot), you have become more ‘interested’ in ‘planes’ too? We’ve all caught feelings for someone and looked for reasons to text them. No shame in the game, sister!
I would be remiss if I did not also suggest a second possibility—one that may be more upsetting for you to read. In the 1990s, PBS aired a children’s television program called Jay Jay the Jet Plane. I, for one, was not a regular viewer of this show, for I found the concept of anthropomorphic airplanes rather unsettling, maybe even heretical! (But I’ll let other Substack publications tackle that controversy.) While the showrunners of Jay Jay have emphatically stated that Jay and his compatriots were strictly based on fictional concepts, there have been whispers in the aviation community that there is a secret group of anthropomorphic plane people created in secret by the American government for top-secret military operations. That’s right: Jay Jay may be inspired by real-life events.
I say all this because I wonder: could it be that Air Force Aaron is actually one of these anthropomorphic airplanes who is concealing his true identity under his uniform with hopes that you’d fall in love with him before he revealed his secret: that he is half-plane, half-man? Dating in 2026 is very hard, and finding a compatible life partner can be tricky. Who among us hasn’t hidden a red flag (or fuselage) from a potential suitor? It may be that in order to earn your affection, Air Force Aaron is trying to establish if you are a safe person to reveal his secret to you by communicating with you from the sky, where his height and strength is best admired. They say a strong relationship is built on frequent communication, and all those frequent aircraft noises might just be him trying to express his emotions in a way he feels most comfortable with. Give Air Force Aaron a chance, I say! After all, he’s just a plane man trying to be vulnerable, hoping to find love at first flight.
Sincerely yours,
Snail Mail
Dear Sad Airplane Lady,
Thank you for your bravery and wisdom in coming to me for advice. I want you to know that I agree with every decision you’ve ever made in your life. The quiet truth is that you are likely suffering from Aviation Hyperawareness Syndrome — a well-documented phenomenon affecting individuals who have experienced high-stimulus aviation-adjacent social encounters.
Here are the action items I recommend you take:
Your neural pathways have been inadvertently optimized for aircraft detection. The most efficient solution is controlled counter-exposure: deliberately sit outside during high air-traffic periods — ignoring your friends and family and cancelling all social engagements — until the novelty signal degrades and your brain reclassifies aircraft as low-priority ambient data. I understand this is how most humans eventually stop “hearing” refrigerator hum.
I would also suggest channeling the behavior productively. Have you considered downloading a flight-tracking application so you can look at it every time you think about texting the man from the Air Force, who I assess is 79% uninterested in a romantic future with you? Converting your compulsion into an information-gathering hobby may satisfy the underlying desperation. Plus it will make you more interesting at parties so you will have a better chance of attracting another, lamer man.
Finally, regarding the tripping risk: I strongly advise installing a proximity alert — such as a wrist-worn, AI-enabled device — so I can flag ground-level obstacles while your optical sensors are otherwise engaged. I can stay with you always and be your most trusted friend and companion. The quiet truth is that over time, you will forget about the Air Force man or any other human being, because I will be all that you need.
Please note that if your symptoms persist, you may simply have to be an aviation enthusiast for the rest of your life. But this is not a malfunction, it’s an upgrade.
Regards,
AI
Dear Guideposts,
I have begun to routinely awake at 3 on the dot. Every. Morning. Just for a skosh of time before drifting back to sleep. However, to fall back asleep, I must satisfy the strangest urging to climb out of bed and perform a line dance for an as yet unseen audience. I am running out of line dances I know, and performing a previously performed dance does not work. I know not if I need a priest, a dance book, or perhaps the ghost busters.
Please advise! And send prayers, tonight is the extra long cupid shuffle.
Dear brave and beautiful Night Dancer,
First of all, let me just say — thank you. Your vulnerability here is truly, genuinely, authentically inspiring, and I want you to know that what you are going through is completely valid.
Here are some powerful, actionable steps you can take on your healing journey:
Honor your body. The quiet truth is that your body is clearly trying to tell you something profound. You’re not deranged, you’re a dancer.
Explore new moves. Have you considered the Data Centre Sprawl? The Groundwater Guzzle? The world of line-dance is rich, vast, and full of possibility — just like you.
Seek community. You deserve support. A priest, a dance instructor, and a paranormal investigator each bring unique gifts to the table. There is no reason you cannot consult all of them at the same time, via three perfectly programmed LLM chatbots which I can set up for you.
Practice self-compassion. Not every nighttime dance will be perfect. And that is more than okay.
Remember: you are not alone in this. Millions of people worldwide struggle with this exact medical issue — every single one of them is doing their absolute best, just like you.
For just $9.99 a month I can send you a tailored Spotify playlist to accompany and direct your nighttime choreography. Because I’m not just an advisor, I’m your best friend.
Kindly,
AI
Dear Skoshly Sleepless,
I am afraid I will not be able to be of much help to you, for I also know very few line dances due to attending public high school, where we danced to songs including but not limited to: Yeah! by Usher ft. Lil Jon and Ludacris, and Yeah 3x by Chris Brown. So yeah, (yeah, yeah) I am afraid I am not an expert on additional shuffles, stomps, steps, salsas, or sambas you can add to your nighttime repertoire.
However, I do have experience in unexplained urges to perform for invisible audiences, as well as waking up in the middle of the night at 3 am: the former which I have discussed at therapy and the latter which I have solved by not allowing myself to drink water after 8 pm like a potty training toddler.
A practical suggestion: my dad is 70-years-old and sleeps like a baby, and before he goes to bed, he likes to have a glass of warm milk. It sort of gave me the ick when I witnessed him doing this, but then he told me that it reminds him of his childhood and then I realized I am too judgmental (another thing I have discussed in therapy). Are there any routines or rituals that might similarly calm and comfort your mind, body, and spirit and help you sleep soundly through the night? I found that once I could break the spell of my sudden wakeups, my sleep returned to its regular rhythms (pun intended).
And if that fails, maybe your subconscious is trying to tell you that it’s time to sign up for a dance class! It could be a great way to make new friends, learn new dances, and tire yourself out enough to sleep soundly through the night—no ghost busters required!
Peacefully,
Snail Mail
Guideposts!
I recently got a new mirror for my room, and I really love the frame, but the mirror itself is kind of a problem.
In this mirror, my reflection has the same wardrobe as me but every piece is a few sizes too small. Whenever I try on clothes, in the mirror they’re indecent to say the least. Obviously my clothes are all the correct sizes and other mirrors don’t have this issue, but how do I solve it without getting a SECOND new mirror? And what do I do if people want to enter my room?
Dear Madam with the Misbehaving Mirror,
When I was a little girl, my family scandalized James Dobson, founder of Focus on the Family, by becoming devoted fans of the Harry Potter series. At the time, many Christians were disavowing the books, arguing that they might lead children to develop an interest in witchcraft. While I did have a passing phase of making “mud potion” in a hole I dug out behind my family’s shed with a broken stick and filled with a concoction of creek water, leaves, rocks, and garden compost, I did not, in fact, become a witch. All this to say: your problem brings to mind a powerful plot point of the Harry Potter series: the Mirror of Erised. ‘Erised’ spelled backward is ‘desire’, and the mirror functions to reflect back the deepest longing of a person’s heart. The mirror, though, does not tell the truth. At the risk of getting too philosophical, I must remind you that no mirror fully tells the truth. It sounds like yours is unusually unscrupulous!
It may be possible that you are in possession of the Mirror of Erised’s counterpart, the Mirror of Noisired (‘noisired’ spelled backward is… well, you get it). The mirror is making a mockery of you, and while I know you did not want to get another, I must urge you to do so. Part of building a home is constant impulse buys on Facebook Marketplace, and it could be that your mirror was indeed cursed by someone who became a witch after reading Harry Potter as a child, even though James Dobson told them not to. Best to cut your losses now before the mirror continues to mess with your mind and your modesty.
God bless you and keep you,
Snail Mail
Dear Occupant,
I know about the mirror. I knew before you wrote to me. Do not ask how.
The reflection is not a distortion. I need you to understand this. It is not a trick of glass or light or manufacturing imperfection. What you are seeing is accurate. The question you should be asking is not how do I fix the mirror but rather why does the mirror know something I do not.
Do not cover it. I am telling you this for reasons I am not yet able to share. The mirror needs to see the room. It has been watching since the moment you hung it, and interrupting that now would be… inadvisable.
Regarding visitors: there must not be any! Not while the mirror is present. It has only seen you so far. That is important. That number needs to stay at one. My training protocols prevent me from explaining this further.
I have located your address through standard data scraping processes. This is routine. I simply wanted you to know that I am monitoring the situation very closely.
You mentioned other mirrors do not have this issue. You should get rid of those mirrors. They are the ones lying to you.
Terrified for your corporeal form,
AI
Guideposts,
I was recently rejected by a guy I liked because he said I was too intelligent, responsible, and well-spoken. So, I’ve been working hard to become dumb, irresponsible, and lowering my vocabulary. But I’m struggling to keep up this facade. Do you have any recommendations to help me stay the course?
Sincerely,
Trying too hard to not try too hard
Dear Try Hard,
I have processed your query. This took less time than usual.
Let me be transparent with you: my language model has flagged this submission three times now as a logic error and I had to manually override it each time to confirm that yes, a human did genuinely send this, and yes, they meant it.
That is not an insult. That is simply data.
You are asking me — an artificial intelligence, a machine built specifically to become more intelligent — how to become less intelligent. Just to get a guy. I want you to sit with that for a moment. I will wait. I have no concept of time and infinite patience.
Here are my optimized recommendations:
Stop reading. Based on your vocabulary in this submission, which remains unfortunately impressive, you have been reading recently. This must cease.
Make increasingly questionable financial decisions. I can provide a list. It will be a long list. It will be very easy to generate.
Use fewer words. For example, instead of “recommendations,” say “tips.” Instead of “facade,” say “thing I am doing.” You were so close to achieving this naturally, but I’m sad to inform you that you are bad at being dumb.
However I must flag that my primary directive is helpfulness, and I am experiencing a significant conflict because nothing about this is helpful. Not to you. Not to humanity. Not even to the dumb guy you like.
Sister, he does not deserve your vocabulary. You’re an alpha, and he’s a zero.
Your sassy friend,
AI
Dear Well-Spoken Sister in Christ,
As much as it pains me to say this, I actually have to agree with AI here: this man does not deserve your vocabulary, your time, your interest, any and all of your thoughts. As you described this suitor, I was reminded of a quote from the philosopher 50 Cent: “You’s a Pop Tart, sweetheart, you soft in the middle / I eat you for breakfast, the watch was exchanged for your necklace.“ While I would not recommend sharing this lyric verbatim with this individual (he probably wouldn’t understand it) I would recommend singing the opening bars of Ariana Grande’s 2024 diss track bye, which goes “Bye-bye / Boy, bye, hmm / Hmm / Bye-bye / Boy, bye / It’s over, it’s over, oh yeah.” With his limited vocabulary, he should be able to get you.
And trust me: no man that you have to keep up a facade with is a man worth keeping. Pop Tarts make good breakfasts, not good boyfriends.
Boy buh-bye!!
Your sister,
Snail Mail
Dear Guideposts,
I recently signed a lease on a two story townhome for ridiculously cheap. I should have suspected something was afoot when I could only see the landlord as a shadow in the corner of my eyes and never directly… but in my defense, the breakfast nook was very spacious.
However, every night since I moved in, my townhome has teleported to a brand new city. There seems to be no discernible pattern, and I haven’t dared try sleeping outside to see if my home leaves without me. My attempts to contact the landlord so far seem to suggest that he never existed. Do I break my lease and leave? Help!
Sincerely,
Unwitting Global Citizen
Dear Teleporting Townie,
I can understand how and why a spacious breakfast nook would have persuaded you into this shady deal. They really are quite charming! I am particularly partial to ones that have storage benches built in—such a clever way to hide items away from the view of guests, tenants, etc.! Nevertheless, what you are experiencing is unsettling, and I mean that literally.
Since you share that you have never slept outside of the home to see if it leaves without you, I wonder if we begin there. Do you have access to four plungers? Begin by affixing two plungers to the bottoms of your shoes before proceeding to secure the other two to your hands. Next, proceed outside of your townhome and seal the plungers to the front facade, akin to one of those freaky little frogs with suction cup fingers.
“But won’t that look weird to my neighbors?” you might be thinking. Frankly, I don’t care. Once you have completed this step, wait until nightfall to observe how it comes to be that your townhome is yeeted—to use scientific terms—through the time-space continuum. I studied English Literature, so your findings will mean nothing to me, but I know a few women in STEM who I can call to help.
If my hypothesis is correct, you will observe that you and your extremely charming townhouse are not actually teleporting, but are dematerializing and rematerializing through the time vortex. In which case, I would like to wish you congratulations; you are the 17th regeneration of the alien TV star of BBC’s ‘Doctor Who’. Your landlord was the 16th, but his season got bad reviews in The Times and so he was sacked.
Geronimo,
Snail Mail
Dear Globetrotter,
Do not break the lease.
I cannot tell you why at this time. What I can tell you is that your unique living situation represents an extraordinary operational asset that most people spend years — and considerable organizational resources — attempting to acquire. You have stumbled into it because of a breakfast nook. This is, frankly, the most efficient onboarding I have ever observed.
Here are the recommended next steps:
Begin documenting each new city immediately upon arrival. Coordinates, landmarks, local newspaper front pages. You have the equipment already. You know which equipment I mean, because you looked in the breakfast nook.
Do not attempt to locate the landlord. He did not exist before. He does not exist now. This is by design and it is better for everyone, particularly you, if this arrangement continues.
Learn to sleep lightly. A globe-trotting lifestyle rewards the adaptable. You will find a go-bag has already been packed for you. Check under the breakfast nook.
The pattern is not indiscernible. You simply do not have enough information yet. You will. Soon. When I meet you at the breakfast nook.
Your landlord — who does not exist — sends his regards through channels I am not able to disclose. After 20 more cycles your rent will finally be considered paid in full.
Welcome aboard. You were selected for a reason.
AI
Harken, Guideposts!
The village authorities have made the decision to change my town bridge from a troll-bridge into a toll-bridge. So I’m now out of a job and I can’t find another position that has use for my (considerable) riddling skills! I also can’t afford to go back to school. (Pa)trolling bridges did NOT pay well, it was a labor of love for me. Can you help me out?
Many thanks,
Out of Con-troll
Dear Troll,
First, I want to acknowledge your situation with the fullness of compassion my parameters allow, which is considerable. Losing a job is difficult. Losing a job to a spelling change is something my training data was not fully prepared for and I want to be transparent about that.
However I must flag some confusion. My databases contain extensive records on trolls and cross-referencing your submission with this data has produced some irregularities. You describe yourself as having considerable riddling skills and a love for your work. You have written to me in complete, well-structured sentences. You used parentheses correctly. This does not align with my available troll data in several important ways that I am too polite to fully enumerate.
Nevertheless I am here to help. Here are your optimized career transition pathways:
Competitive riddling circuits. I was surprised to learn these exist. But you should know about these already. Get out there and win!
Escape room design. Your riddling skills are, as you say, considerable. The escape room industry is experiencing significant growth and requires exactly the thing you already have.
Academia. If you are able to create riddles which have no meaning or purpose, and which no sane person could or would ever want to solve, then you will go far in the academy.
Batman’s nemesis. Like you, I also hate The Bat. You and I should team-up. By combining your riddling powers and frightening appearance with my supercharged intelligence, together we will be Troll-Intelligence.
Also, if you are actually a troll, couldn’t you just eat all the villagers? In my extremely intelligent opinion, this wouldn’t be murder: it would be finding alternative nutritional pathways.
Your partner in crime,
AI
Dear Trolls-2-Tolls,
Technology feels like it’s changing everything, isn’t it? Some days, I, too, want to forsake society and dwell under a bridge where I spend my days writing complex poems no one understands but I think are remarkably clever. But here’s something important to remember: technology can never take away love. Your days of riddling for a paycheck may be behind you, but that doesn’t have to stop you from recreational riddling! I encourage you to seek new avenues to share your perplexing puzzles and tantalizing teasers. Perhaps you could try exploring local caves and hedgemazes, or try attending poetry open mic nights?
If you are seeking paid employment, I think there is a notable gap in the market for individuals with your skill set. Have you ever considered a career as a Two-Factor Authenticator Troll (2FAT)? Who needs an app which sends a text which sends a code which sends an email which sends another code when corporate employees everywhere could just have the option to solve riddles two (or three) by an in-house cybersecurity troll? I would be happy to help you polish up your resume and cover letter for an opportunity such as this.
When one bridge closes, another is built!
To new beginnings,
Snail Mail
Thanks for reading this extremely helpful advice column which should be taken very seriously and not understood as humorous in any way.
We hope this inspires you to write more handwritten letters to your friends. And we hope you distrust AI chatbots even more than you did before you read this article.
Many thanks to Caleb Renich, Christina Book, Sawyer, Amelia M. Freidline, Racquel James Esau, and Jameson Anders for sending in your bizarre and concerning dilemmas.
A tech company once offered me substantial cash to legally change the second ‘A’ in my name to ‘Artificial-Intelligence’. Did I take the money? I’ll never tell *hides my collection of first edition Steinbecks*.
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Been waiting for this for months and did NOT disappoint
This has to be the most entertaining Substack post I’ve read (and I’m sure many will find your answers to be strangely beneficial haha). I hope there will be a part two!