When the Hypotheticals Get a Lot More Specific
There was a version of Fuck, Marry, Kill that worked perfectly at 2 a.m. in a shared room with a mini-fridge humming in the corner. The choices were celebrities, fictional characters, people from class – nothing with legal standing, nothing that required a notary. The game was disposable by design. Nobody was going to remember what you said by morning, and the consequences of choosing wrong were exactly zero.
Middle age has a way of recalibrating the stakes. The New Yorker recently surfaced a version of the game updated for the actual conditions of adult life, and the three options on the table are: income-tax returns, life-insurance policies, and that folder explaining benefits that you received from H.R. when you were onboarded – and then immediately lost. Which raises the question of whether any of us are actually equipped to play.

Three Contestants, One Exhausted Adult
Start with income-tax returns. They arrive annually with the dependability of a bad ex, they know more about your finances than you do, and there is no graceful way to handle them. You either hand them off to someone else entirely or you spend three weeks telling yourself you’ll start soon while the deadline quietly advances. On the other hand, they are technically functional. They do what they’re supposed to do. There is an argument – not a romantic one, but an argument – for keeping them around.
Life-insurance policies occupy a different psychological register. They exist in the category of things adults are supposed to have, nod seriously about at dinner parties, and understand in principle while avoiding in practice. A life-insurance policy makes you think about your own death, the financial stability of the people you love, and the actuarial tables that have already assigned you a number you don’t know. Marrying a life-insurance policy means committing to the long game. It means sitting down, reading the document, understanding what “term” versus “whole” actually means, and accepting that this relationship will only really pay out after you’re gone. It is the least romantic proposition in the history of the game.
And then there is the H.R. benefits folder.
This is where the comedy becomes something closer to archaeology. The folder arrived on or around your first day at a job – probably slid across a desk, possibly emailed as a PDF with fourteen attachments, maybe handed to you in a manila envelope while someone in a lanyard explained the dental plan with the enthusiasm of a person who had explained the dental plan four hundred times before. You nodded. You said you’d read it later. Later was a very long time ago. The folder, if it still exists, is almost certainly in one of three places: a drawer you haven’t opened since the Obama administration, a cloud folder with a name like “Important – MISC,” or nowhere at all, because you moved apartments twice since then and it simply didn’t make the cut. Killing the H.R. benefits folder is not an act of malice. It is a mercy. It is also something you have already technically done.

What the Joke Actually Knows
Humor about administrative paperwork only lands when it’s pointing at something real, and what this particular premise points at is the quiet gap between who we intended to be as adults and who we actually are. The intended adult filed things. The intended adult read the benefits summary, understood the FSA contribution limits, and made an informed decision about the supplemental life-insurance rider. The actual adult has a general sense that health insurance exists and a very specific memory of the last time they needed it and couldn’t find a single relevant document.
That gap – between the organized, financially literate person we assumed we’d become and the person currently Googling “what is a deductible” at age 44 – is where middle-age comedy lives. It’s not about failure, exactly. It’s about the particular exhaustion of realizing that adulthood is mostly paperwork, and that the paperwork never stops, and that the folder you lost in 2011 has been replaced by a newer folder you are already in the process of losing.
The Actual Difficulty of the Question
Here’s what makes the updated version of Fuck, Marry, Kill genuinely harder than the original: there are no objectively bad answers, because all three options have real consequences. Ignoring your tax returns creates problems. Letting your life insurance lapse creates problems. Never reading your H.R. benefits folder means you are almost certainly enrolled in the wrong health plan and have been for years. The college version of the game was consequence-free by construction. This one is not.
You could argue that the income-tax returns deserve the most commitment – they show up every year, they require action, they determine whether the government owes you money or you owe the government money, and that relationship is not optional. Marry the tax returns. Learn to live with them. Make peace with TurboTax.
The life-insurance policy, by contrast, might be better suited to a passionate but finite engagement. Get one. Understand it. Set a reminder to review it every five years. Do not attempt to build your entire emotional life around it.

Which leaves the H.R. folder. The one with the laminated card that listed the employee assistance hotline, the section on tuition reimbursement you meant to use, the page explaining how to roll over your 401(k) when you eventually left for a different job – which you did, without rolling anything over. That folder deserved better. It also deserved to be read before it disappeared. Somewhere in an office filing system, there is probably a record of the person you were supposed to become on day one of a job you may no longer have, organized and prepared and ready. The folder is gone. That person is probably fine.






