My AI assistant emailed four of my friends from my inbox and picked which one I'
By Alliekmiller · November 7, 2026 · Curated by George's Blog
My AI assistant emailed four of my friends from my inbox and picked which one I'd spend Saturday with.
I gave dot (OpenAI's new always-on AI agent) a $500 budget and almost no rules. The day itself was great and included stamp workshop, art gallery, and dinner at a place neither of us had heard of. Most of what went wrong was on me, like I never told it when to give up on a restaurant (it kept asking the same one for a table until I had to apologize) and I never told it my friends text (It emailed all four of them).
Here's the note I'm giving it before round two:
✅ Ask a place twice, then move on.
✅ Text friends. Email businesses.
✅ Anything that costs money or speaks for me, check with me first.