Most people revel in milestones. Turning the yearly page on birthdays, holidays and anniversaries is an opportunity for big parties, exchanging nice gifts and celebrating the ones we love. It can also be a minefield of missed connections and hurt feelings if you forget the dates.

If you’re ever sent a “happy belated birthday” message, neglected to recall your own anniversary or simply struggle to keep in touch with people, this guide might be for you. Granted, you’ll have to put your trust in an AI agent to do the heavy lifting, but you might never need to remember to send a card again.

While AI may not understand human connection and happiness, what it does well with is rote tasks. I tried to use ChatGPT and a few other AI tools to automate the upkeep of my personal and professional relationships — but here’s where it all went wrong.