How-to

How to plan a group trip with AI (and end the 200-message thread)

Updated September 2026 · 5 min read

Every group trip has the same three problems: nobody says their real budget, one person does all the research, and the decision never gets made. An AI in the group chat fixes all three, if you use it the right way.

Step 1: Put the AI in the chat, not in your DMs

If you plan alone with a chatbot and paste the result into the group, you've just become the person who does all the research, with extra steps. The point is to have the AI where the group already is. In SharedChat, start a Friend Groups room and text the link; everyone's in with one tap.

Step 2: Get the constraints on the record

Ask everyone for three things in the thread: dates they can do, a real per-person budget, and one dealbreaker ("I won't share a bed," "I can't drive more than 3 hours"). People say honest numbers in a room with an AI referee that they'd never say to the group's loudest planner.

Step 3: Drop in the options and ask it to pick

Paste the two or three listings you're considering and say: "Pick one for 8 people, show the per-head cost and drive time, and say who gets the worst sleeping spot." A good room answers with a decision, the math, and the trade-off, not a list of considerations.

Step 4: Let it settle the tie

Split 4-4? Move it to a Settle It room and let the Judge rule. It sounds silly until you realize nobody's feelings get hurt when the referee is a robot.

Step 5: Ask for the summary

"Give me the plan in five lines with who owes what." Pin it. That's the message people will read.

Prompt that works: "We're 8 people, dates June 12-15, budgets $150-$300 each. Here are three listings. Pick one, show cost per person, and flag any dealbreakers from what people said above."
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