---
title: My most memorable anniversary
date: 2026-06-03T09:27:14+08:00
categories:
  - llms
description: I saved my 24th anniversary by using ChatGPT to analyze bank transaction data for gift ideas. I ended up spending the day finishing 24 tasks from my wife's to-do list, which she called her most memorable anniversary.
keywords: [chatgpt, llms, data analysis, personal productivity, gift ideas, prompt engineering]
---

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.

<!-- https://chatgpt.com/c/6a1d867e-47bc-83ec-b25f-54d858826d24 -->

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](https://www.s-anand.net/blog/birthday-sandwich-cake/) 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."

![](https://files.s-anand.net/images/2026-06-03-my-most-memorable-anniversary.avif)

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