I Let AI Manage My Social Life; AI Texted Friends and Picked My Outfit

I’ve been quietly outsourcing more and more of my life to AI. It started with work tasks and writing prompts. AI even helped me land my latest job. Now, with “agentic AI” and autonomous agents making headlines, the possibilities have multiplied.

So, I started to wonder: if AI is so good at optimizing my professional life, could it do the same for my personal one? Could ChatGPT, Claude, Gemini, or Grok plan my week better than I could? Would it make me more connected or just more robotic? Would people notice a difference? Would I care?

I decided to run the experiment, fully prepared for things to get weird.

Laying down the ground rules for my AI takeover

Out of all the main AI players, I picked ChatGPT, partly because it already knew me — maybe a little too well — and because it’s the only AI subscription I pay for. My chat history includes everything from therapy-adjacent venting and restaurant scouting to career planning, creative brainstorming, and fashion advice.

The kicker: I’d just been granted access to OpenAI’s Agent feature, essentially an AI that can take action on your behalf. It can book reservations, pull live data, and organize tasks without you pasting in every detail.

At first, it was unsettling. The idea of a chatbot having conversations for me felt like handing my personality to a stranger. Following instructions about where to eat or what to wear felt alien. We even spoke through ChatGPT’s voice mode to give it more context, which was weirdly intimate, like confiding in a personal assistant who never blinked.

The upside? My account usually gives me a couple of options when I ask for something, so I still had some say. And soon, the weirdness faded.

The warm-up: errands, Netflix picks, and borrowed small talk

The first few days were low-stakes. My focus was work, so ChatGPT handled the easy-to-outsource stuff: building my grocery list, finding a new Netflix series that actually matched my taste, and answering a few casual text messages from friends.

Things got interesting on Thursday, when weekend messages started trickling in. A good friend texted: “What are you doing this weekend?” Normally, I’d give a vague “not sure yet” and figure it out later. This time, I showed ChatGPT the text.

Seconds later, my friend had a cheerful, fully formed plan that I hadn’t even thought about, and I’d barely lifted a finger.

From tourist traps to compliments on my shirt

Saturday night’s AI-chosen “top-rated” Italian restaurant was a miss: laminated menus, bored waiters, and a room packed with tourists snapping photos of their food. It was not terrible, but it did not have the hidden gem energy I like.

Sunday’s brunch, though, was a win. At brunch, one friend raised an eyebrow.

“Since when do you book places more than five minutes in advance?” she asked. I admitted the reservation came from my new personal assistant, and by the time the pancakes arrived, she was pitching ways to outsource our entire social calendar to it.

Also, I asked ChatGPT to pick my outfit on Saturday, based on male fashion trends and what it already knew about my wardrobe. Interestingly, it chose a bold patterned shirt I’d normally shove to the back of the closet. I wore it, got more compliments than I’ve had in months, and started to wonder if maybe AI knows something about my confidence that I don’t.

Letting AI plan my week showed me what I actually value

What surprised me most was how much I overthink the simplest plans. With the busywork handled, I felt lighter and freer to be present instead of mentally juggling what’s next.

It wasn’t flawless. AI can’t tell the difference between “highly rated” and “actually worth going to,” and some of its messages had a faint uncanny valley vibe. But its mistakes — the tourist-trap dinner and the overly enthusiastic RSVPs — became moments of genuine connection among friends. We laughed about them. We improvised.

There was also a strange intimacy in letting AI into my social life. I noticed patterns I hadn’t before: I often delay responding to invitations, default to the same three restaurants, and am more adventurous with clothing when someone else makes the call. Those nudges made me aware of my own habits in a way that felt oddly personal.

In the end, outsourcing my week didn’t strip away my humanity. It highlighted it. By handling the logistics, AI left me with more bandwidth to listen, to laugh at the awkward bits, and to embrace the unpredictability that makes social life worth having.

Would I let AI run my personal life forever? No. But for one week, it didn’t just make my life more efficient. It reminded me of what’s actually human about being social: showing up, enjoying the company, and letting the unexpected make the best memories.