A Boston TikTok creator’s story about an expensive work dinner has sparked a broader conversation about restaurant etiquette, company spending, and whether employees should ever order the priciest item on the menu when someone else picks up the tab. The creator, Jay (@.jaydave), shared the story in a July 2026 video after offering one piece of advice: “Never order a market price item at a restaurant without checking the price first.” According to Jay’s TikTok, the lesson came from a company-sponsored holiday dinner where his manager encouraged employees to “order whatever you want.” Believing the meal was a chance to enjoy a special night without paying out of pocket, Jay decided to splurge. “I want to ball out a little bit cause my company was paying,” he said in the video. “It’s not coming out of my pocket.” Jay opted for the largest serving. That decision led him to order the surf-and-turf, which included a 12-ounce filet and lobster, he said. Things became more expensive when the server asked how much lobster he wanted. Jay said he did not understand how lobster portions worked at the time. After hearing he could choose one pound, one and a half pounds, or two pounds, he opted for the largest serving. “Not realizing how absurd that actually is,” he recalled. Only after the meal did he realize what that choice meant. @.jaydave Lesson learned #market #price #restaurant ♬ original sound – Jay “Little did I know the check was gonna come. My own personal meal was like $175,” Jay said. Although his manager had encouraged everyone to enjoy themselves, Jay said he immediately regretted his decision. “I felt so bad,” he said. “Granted, he did say, everybody order whatever you want, I was just listening, but I did not need to take it that far.” According to Jay, the large dinner bill later drew scrutiny from company leadership, leaving his manager to explain the expense. “He ended up getting, like, in trouble with, like, the higher-ups of my company,” Jay said. He added that his boss defended the decision by explaining it was a Christmas celebration and that employees had been told they could order freely. Looking back, Jay said the experience taught him to ask questions before ordering expensive items, especially those listed at market price instead of a fixed menu price. “If I knew it was gonna cost that much money, I would have never ordered that,” he said. “I would have just got a steak or just got lobster,” because he didn’t need both. The story prompted plenty of reactions and comments, where viewers debated who should bear responsibility for an unusually expensive business meal. One commenter wrote, “I hate when companies do that.” Another argued, “If you’re ordering market-price food, be in a position where the price doesn’t matter.” Others felt the company overreacted. One commenter wrote, “$150 is nothing for the company. That’s like the equivalent of a $2000 year salary bump. And they get to write it off.” Despite the debate, Jay said his biggest takeaway had nothing to do with lobster itself. Instead, he urged diners to ask about market pricing before ordering, even if they worry it might feel awkward. “I know you don’t wanna be that guy who’s like, ‘Oh, how much does this cost?’ Cause you look like an idiot,” he said. “But trust me, I learned this the hard way.”