I successfully haggled with an AI garage sale by empowering it

Haggling is awkward and erratic at the best of times, even when you're bartering with an AI.

In a highly addictive project spotted by TechCrunch, you can debate prices with an AI Garage Sale, an artificial intelligence bot selling items of varying value. It's the work of Los Angeles art studio Brain, and according to the publisher, it's mainly powered by OpenAI with intensive training to learn the ins and outs of bartering.

Amid the Cyber Monday madness, it's a neat way to play around with AI and online shopping. I tried haggling with the AI a few times with various items on sale: a 1997 Tamagotchi, one of those old Big Mouth Billy Bass wall plaguers, a copy of Cyrus A. Parsa's book Artificial Intelligence: Dangers to Humanity, an Untitled Folder Wallet designed by Nikolas Bentel, a roll of $1 George H.W. Bush presidential coins, one issue of Portable Restroom Operator mag — the random range of items you'd actually find at a garage sale.

I was way too skeptical and unsure to spend actual money on any of these items (as you should be too), but it's a blast trying to haggle down the price with these rather enthusiastic AI sellers.

Each time, the AI has a new name and backstory, details of which it will wield to bargain with you, whether they need extra cash for a gift for their granddaughter or they have a high-pressure boss urging them to make the sale. The AI will often try and equate the price with something cheaper, like "two fancy coffees", and learning to actually do the math on that and call it out helped me bring down the price.

In an unusual garage sale find, I managed to get two pit tickets for Olivia Rodrigo's sold out GUTS tour show at Madison Square Garden $3,689 down to $2,940 by bonding over ludicrous ticket prices, but still a towering sum considering pit tickets went for $464.50. I haggled on a physical certificate entitling the holder to one share of Tesla Inc for $481 — Tesla stocks are currently sitting at $236.08.

But my most effective method of haggling, beyond directly asking "can you make this cheaper", was deeply human. I managed to barter most effectively when professionally empowering the AI bot, empathising with their long hours or getting them to vent about their boss.

Turns out the best way to connect with an AI seller is with the most human traits.