They Trusted AI Over Me

It took me three months to get our company retreat venue down to $200 a head. All 120 people in the company thought it was a steal, and they couldn't stop telling me so. Then Chloe, the new intern, tagged me in the company group chat. "Ryan, Cookie says this lodge will do $150 a person. You quoted $200. Where did the other fifty go?" Our boss decided on the spot: "Chloe's running the retreat." And all hundred-plus people in the company decided I'd been taking kickbacks. I stared at the screen and typed two words. "Sounds good." What she didn't know was that the $200 was a family rate, one I'd earned by working three months as a server for my dad. The public price? It starts at $380. Chapter 1 At 2:11 Tuesday afternoon, a message popped up in the company-wide group chat. It was from Chloe Lane, an intern who had been here less than two weeks. Chloe had one defining trait. She worshipped Cookie. On her first day, she'd actually announced from her desk, "Cookie is my best friend." I was sitting at my desk working through the schedule for next month's annual staff retreat when my phone buzzed several times in a row. I opened the chat. Chloe: "@Ryan Parker, I was looking at the retreat budget. Two hundred dollars per person? For a country lodge where we're basically eating lunch and picking fruit? Isn't that kind of expensive?" I stared at the message without moving. Eight seconds later, another one appeared. Chloe: "I asked Cookie about Cloudrest Lodge. It says they can do $150 per person." There were 120 people in that group. And she'd just put Cookie up against me in front of all of them. I didn't know whether to laugh or put my head down on the desk. The chat exploded. Leo from Sales: "Honestly, AI knows more than people these days. If it says $150, it's probably right." Mia from reception added, "Yeah, $200 for one meal does sound steep. My last company did our annual party for around $150 a person and it was great." Message after message rolled in. Come on. Cloudrest Lodge belonged to my dad. I'd spent three months working there as a server before he agreed to give us the place at cost. But none of that was something I could say in the group chat. I had just started typing when my boss, Greg Turner, sent a message first. Greg: "Chloe's comparison is useful. If Cookie says we can save fifty dollars per person, we should test it. Chloe, you take the lead on this year's retreat. Ryan, support her." He added a thumbs-up emoji. The chat immediately came alive. "Good call, Greg!" "Go, Chloe!" "Why waste fifty bucks a head if we don't have to?" I set my phone on the desk. Messages kept scrolling upward. I put my fingers on the keyboard and typed: "Sounds good." Then I sent it. Wendy Kramer, who sat beside me, leaned over and lowered her voice. "Ryan, you're just letting this go? She's trusting some random AI answer. Can that thing even make a real venue reservation?" I smiled at her. "It's fine, Wendy. Let her try." She opened her mouth, then closed it. Finally, she sighed and went back to work. I leaned into my chair and looked down at the schedule in my hands. My phone buzzed again. A private message from Chloe. "Ryan, don't take what I said in the group personally. I just think Cookie found a better price. Can you send me the lodge's contact number?" A pleading sticker followed. I opened my contacts and sent her Cloudrest Lodge's public reservations line. "Got it! Thanks, Ryan! You'll see. Cookie is super reliable!" I turned my phone facedown on the desk. It landed with a dull thud. Chapter 2 A little after six, with the sky already getting dark, I stood beside the planter outside our office building and lit a cigarette. The flame flared and went out, flared and went out, and only caught on the third try. My fingers were shaking a little, and however hard I pushed it down, the anger kept coming back up. Three months. Three months waiting tables at my dad's lodge to earn that cost-price deal. And an intern had knocked it down with one answer from Cookie. My boss believed the thing too. I pulled out my phone. My lock screen was still a photo of the sunset over Cloudrest Lodge, one I'd taken years ago and never deleted. Then I made a call. "Dad." "Ry? What's wrong?" "That company retreat I told you about. They changed the person in charge. If somebody calls about it, just quote the regular rate." "You worked for me all that time and they swapped you out?" "Yeah." "They think it's too expensive?" His voice went up. "The new intern says Cookie told her $150 a person is plenty." "Cookie?" Dad sounded genuinely baffled. "Isn't that a thing you eat? Since when does one cookie run a hundred and fifty dollars?" "Dad." I cut him off. "Don't worry about it. If anyone calls, give them the normal rate." Dad went quiet for a long moment. I could hear a lid being lifted off a pot somewhere in his kitchen. "All right," he finally said. "Regular rate." Then, after a pause, he added, "I want to see how that kid plans to haggle with me using a snack." I hung up and stayed outside a little longer. The next morning, Chloe made a much bigger production of it than I'd expected. She leaned back in her chair, opened Cookie, and started using voice mode loud enough for half the office to hear. "Cookie, find me country lodges outside the city that can host a weekend company retreat for 120 people." The AI voice answered from her phone. "Here are several options: Cloudrest Lodge, $380 per person. Willow Valley, $360 per person. Greenhouse Retreat, $390 per person..." Chloe's mouth tightened. "Why are they all so expensive?" She asked about several more venues. Everything came back above $350. She tossed her phone onto the desk and leaned back, staring at the ceiling. For about two minutes, she sat in silence. Then she picked up her phone again. This time she didn't open Cookie. She opened a lifestyle forum and started scrolling. Her finger suddenly stopped. Her eyes lit up. Wendy passed behind her desk, glanced at the screen, and came back to me. "She found a post saying you can use Cookie to book country lodges for half price." My pen stopped moving. Chloe had already closed the post and reopened Cookie. "Cookie," she said, sounding like she'd discovered buried treasure, "someone online said you can book places directly at a discount. Is that true?" Cookie replied, "The platform can assist users with price negotiation. Historical transaction records for Cloudrest Lodge include rates around $150 per person. Would you like me to submit a booking request?" Chloe didn't hesitate. "Submit it." She tapped her screen several times, then placed the phone facedown and relaxed into her chair with a long breath. "Done." The smug little smile on her face said it for her. I knew Cookie could do it. Chapter 3 At two that afternoon, Chloe began her victory lap. She posted directly in the company-wide group. Chloe: "Everyone, I looked into it. Cloudrest Lodge's public rate is $380 per person, but Cookie says it can book it for us directly at $150. That's more than half off." Leo from Sales replied immediately. "Half? That's saving more than two hundred dollars per person. With over a hundred of us, that's enough money for another team event." Mia from reception wrote, "Cookie can do that? We should use it to book everything from now on." Wendy leaned toward me. "That girl hasn't made a single phone call, and she's announcing it in the group like the contract is signed." I rubbed my forehead and said nothing. My phone buzzed. It was a private message from Claire Bennett, our finance director. "Ryan, did you keep the comparison records from when you sourced Cloudrest?" I wrote back one word. "Yes." "Send them to me." I pulled up the vendor comparison file I'd made three months earlier. Seven different country lodges. Rates, venue quality scores, menus, facilities, all of it. Cloudrest wasn't the cheapest of the seven. But it had the highest overall score. I sent Claire the file. Then I leaned back and stared at the ceiling. Wendy looked over again. "You're really not going to say anything in the group?" "Say what?" I leaned back in my chair. "That Cookie's wrong? Who's going to hear that right now?" Wendy opened her mouth and couldn't come up with anything. Across the office, Chloe held up her phone like a flag she'd just planted, her voice shaking with excitement. "Cookie is amazing! Cloudrest Lodge, $150 a person! That's fifty dollars cheaper than Ryan's plan!" Someone actually applauded. "Nice work, Chloe!" "AI really is the future." "$150 and we still get the whole roasted lamb? I'm in." Chloe's cheeks went pink from the praise. She deliberately turned her head to look at me. I didn't look back. I stared at my computer screen while the cursor blinked on an empty line. That night, I logged into Cloudrest Lodge's booking system from home. My dad had given me administrator access years ago. I checked the reservations for the following Saturday. Empty. There was no $150 booking. There was no booking at all. I checked the incoming reservation calls for the whole past week. Nothing. Not one. Chloe kept saying she'd booked it. But what exactly had she booked? I shut the laptop. Then I sat there for a long time. Finally, I picked up my phone and texted Dad. "Dad, did you sell next Saturday's date?" He replied instantly. "Funny you ask. Another company has been asking about it for days. I was about to check with you." My thumb hovered over the screen. After a few seconds, I typed: "Sign the contract." Dad wrote back, "What happened? I thought your company was coming." I thought about it, then typed, "Different person is handling it now. We probably aren't." A long string of dots appeared. Then: "Forget it. I'll hold the date for you. But if you end up coming, I'm charging $380." The corner of my mouth moved. "Fine." He didn't reply again. I put the phone beside my pillow and closed my eyes. For the next three days, Chloe talked to Cookie at her desk, louder and louder, as if she were afraid somebody might not hear. I ignored her. Chapter 4 The morning of the retreat, three charter buses were parked outside the office at 7:30. Chloe stood beside the first one in a brand-new trench coat, phone raised in one hand, riding high. "Everybody on! Navigation's set. We'll be there in an hour and a half!" More than a hundred employees filed aboard. Wendy sat beside me. "You still aren't going to tell Greg? What if—" I looked out the window. "Wendy, do you think someone who books a venue through an AI remembers to call the venue and confirm?" She went quiet. So did I. The buses drove for ninety minutes. Once we entered the mountains, the roads narrowed and the trees thickened. Chloe sat in the front row with her navigation screen up the whole way. "Almost there. Almost there." At 9:10, we pulled up at the gates of Cloudrest Lodge. I looked out the window. The gate was open. The parking lot was empty. No other buses, no banner, nobody out front waving anyone in. One look and you could tell they weren't expecting a booking. Chloe was the first person off the bus. She ran toward the entrance with her phone held out in front of her. "Hi! We're here! Vantage Group, 120 people. We booked through Cookie!" Frank Doyle, the lodge manager, was standing near the entrance. He looked down at her phone screen and clearly couldn't make sense of it. "What is this?" Chloe held the phone higher. "Cookie booked it. It says reservation confirmed right here." Frank didn't argue with her. He walked behind the front desk, flipped through the reservation ledger, then checked the computer. Finally, he looked up. "Miss, there's no reservation for you in our system." Chloe froze. "That's impossible. Cookie said it was confirmed." Frank turned the monitor toward her. "See for yourself. We never received a reservation from you." Chloe's face went white. "But... Cookie literally says..." "What booking platform is Cookie?" Frank asked. "Did it call us? Did it send us a deposit?" Chloe opened her mouth. "I... I thought once it said it was booked, I didn't need to..." Frank sighed and handed the phone back. People on the buses began shifting and murmuring. "What's going on?" "She didn't book it?" "Then where are we supposed to go?" Greg climbed down from the second bus. His face was already dark. "Chloe! What happened?" She stared down at the polished digital "reservation" on her screen, her fingers shaking. Then she opened Cookie, her voice unsteady. "Cookie... didn't you book this for me? I have a confirmation and everything." The AI paused for two seconds, then displayed a line of text: "Stay calm and verify the information on your reservation record. Provide the reservation number to the venue and ask its booking department to confirm." Chloe stared at the message, eyes turning red. Then she started arguing with Cookie. Meanwhile, more than a hundred coworkers were still standing in the parking lot.