When Jess was set up on a disastrous date with Stewart, it quickly spiraled out of control at a swanky restaurant. What was meant to be a casual evening turned into a nightmare when Stewart’s credit card was declined and the manager threatened to call the police. “Jess, you gotta meet this guy,” Adam said, sprawled out on the couch and flipping through TV channels. “Stewart. Works with me. Real stand-up guy. Stable job, nice car, the works.”Jess barely looked up from her laptop. “Who’s this guy?” “Stewart. Trust me, he’s different. You’ll like him.” “Another setup?” Jess asked, rolling her eyes. “No, seriously. He’s asking about you. I think you two will hit it off.” Jess sighed, her skepticism palpable. “Alright, but if this turns out to be another dud, I’m never listening to you again.” “Deal. You’ll thank me later,” Adam said with a smirk. After hours of getting ready, Jess’s apartment looked like a tornado had struck.
needing to regroup. A text from Adam buzzed on her phone: “How’s it going?” Jess stared at the screen, fuming. She splashed water on her face and tried to steady her nerves. When she returned, Stewart was still arguing with the waitress and the manager. The security guard had joined the scene, warning that they might need to involve the police. Stewart looked at Jess with desperation. “Can you help out? Just this once?” “I can’t. I don’t have that kind of money,” Jess said, feeling trapped.Her phone buzzed again. Another message from Adam: “How’s the date going there, Sister? ;)” Jess showed Stewart the text. “Did Adam know you couldn’t pay?”Stewart looked confused. “I don’t know. Adam set this up, and he said he’d put money in my account. Looks like he didn’t.” Jess turned to the security guard. “Please, can we step outside? I’ll call someone to settle the bill.” Outside, the cool night air did nothing to alleviate the tension. The security guard kept a close eye on them as Jess called Adam, her anger barely contained. “Adam, Stewart can’t pay the bill. It’s huge! What did you do?” Adam chuckled. “Relax, Jess. Just adding a bit of excitement. Use your card if you have to.” “Are you kidding me? Get down here and fix this mess!” “Alright, alright. I’m on my way,” Adam said, still amused. When Adam arrived, he was still grinning. “Hey, folks. Problem with the bill?” “This isn’t funny, Adam. You’ve humiliated me,” Jess snapped. Adam shrugged. “I thought it would be fun. I’ll cover it. Chill out.” Moments later, Adam returned with a receipt. “There. All settled. Happy now?” “You think this is a joke? You crossed a line,” Jess said, her voice sharp. Adam seemed unfazed. “It was just a prank. I wanted to spice things up.” Stewart looked at Jess, then at Adam. “I’m really sorry. I had no idea.” “It’s not your fault,” Jess said, her gaze fixed on her brother. Adam, still grinning, gave Jess a playful punch on the arm. “Come on, Jess. It wasn’t that bad.” Jess shook her head. “You don’t get it, Adam. You went too far.” As Adam walked away, Jess turned to Stewart. “I’m sorry about tonight. I didn’t expect any of this.” “It’s okay,” Stewart said quietly. “I understand.” They shared a moment of silent understanding before parting ways. Jess walked home, feeling betrayed by her brother and contemplating new boundaries for the future. What would you have done in Jess’s situation? If you enjoyed this story, here’s another one for you about a waitress who texted with a stranger, pretending to be a woman he’d met before.