It 9:30 pm, I checked my calendar for tomorrow’s appointments, alt-tabbed frantically into ChatGPT, and started typing:

Tomorrow is my 24th anniversary. It’s a bit late for me to buy anything (except maybe an online service) or prepare something.

This has become a habit – leaving things to the last minute and asking ChatGPT to save my day.

I did give it good context, though.

You remember the OCBC expenses treemap you created by analyzing my transactions? That will give you a good guessable idea of the kinds of things she spends on and hopefully, therefore, what she likes.

I was analyzing my bank transactions over the weekend, so that came in handy.

What can I do (either create for her, like I made a peanut jelly nutella sandwich birthday for Dhyeya or buy - if it’s an online service / gift voucher kind of thing) in the next hour or so?

ChatGPT began with gyaan - which I promptly ignored:

Your best move is not “buy a gift”. It is “prove that I have noticed your life, then attach a redeemable escape hatch…

… and moved on to analyzing her personality and recommending from different perspectives:

Practical person

  1. No-decision day: “Tomorrow, you decide nothing. I handle transport, food, booking, payment, and exit plan.”
  2. Service relief voucher: 24 hours where she forwards any household/admin nuisance to you.
  3. Personal-care float: ClassPass/spa/salon voucher plus the promise: “I will book the slot and taxi, not just give you a coupon.”

A romance playwright

  1. 24 tiny vows: not grand vows; operational vows: “I will stop asking where the charger is.”
  2. The ordinary-places pilgrimage: one route across 3-5 mundane but meaningful places.
  3. Private audio guide: 8 short voice notes she unlocks at home / taxi / restaurant / temple.

… and so on.

For some of these, I’m absolutely the worst person to execute. ClassPass? Spa? Salon? I don’t even know the difference between them.

But 1.2 and 2.4 were interesting. So, after a few iterations with ChatGPT, I woke up the next morning with:

Today’s our 24th anniversary. For the next 24 hours, I’m going to knock off 24 things from your TODO list.

I rescheduled my meetings. I spent the entire day doing nothing but what was on her list. Water purifier, doctor appointments, toothbrush shopping, investments, drying clothes, duct-taping, … and we dined out.

At 10:00 pm: “I think it was my most memorable anniversary. Thank you.”

Thank you, ChatGPT. Thank you, habit of setting low expectations.