When Jess agreed to go on a date with Stewart, she had no idea it would turn into such a disaster. What was meant to be a casual evening quickly spiraled into chaos at a fancy restaurant when Stewart’s credit card was declined, and the manager threatened to call the police.
It all started when Jess’s brother, Adam, tried to play matchmaker once again.
“Jess, you’ve got to meet this guy,” Adam said, lounging on the couch and flipping through TV channels. “His name’s Stewart. He works with me. Really solid guy. Stable job, nice car, all that.”
Jess barely glanced up from her laptop. “Who’s this guy?”
“Stewart,” Adam repeated with enthusiasm. “Trust me, he’s different. You’ll like him.”
“Another setup?” Jess asked, rolling her eyes.
“No, seriously. He’s been asking about you. I think you two will hit it off.”
Jess sighed, clearly doubtful. “Alright, but if this turns out to be another disaster, I’m never listening to you again.”
“Deal. You’ll thank me later,” Adam said with a smirk.
After spending hours getting ready, Jess’s apartment looked like a tornado had hit it. But Adam’s pep talk had convinced her to give it a try. Stewart arrived in a sleek, shiny sedan that smelled like new leather. Jess slid into the passenger seat, feeling a mix of nerves and curiosity as the engine purred smoothly beneath her.
“Hey, Jess,” Stewart greeted with a warm smile. “Nice to meet you.”
“Nice to meet you, Stewart,” Jess replied, trying to stay calm.
“I thought we’d go to this new place downtown,” Stewart said confidently. “It’s fancy, but the food is amazing.”
“Sounds good,” Jess said, hiding her surprise at the upscale venue.
The restaurant was a picture of luxury, with sparkling chandeliers and white tablecloths. Jess felt a bit out of place, but Stewart seemed right at home. He led her to their table with ease and charm.
“Order whatever you like,” Stewart said, dismissing Jess’s hesitation over the pricey menu.
“Thanks,” Jess said, feeling a little more at ease. The evening began smoothly. Stewart was charming and engaging, and Jess found herself laughing more than she had in a long time.
Then, the bill arrived.
Stewart handed over his credit card with a flourish, but the waitress came back with a worried look. “I’m sorry, sir, but your card was declined.”
Stewart’s face fell. “That’s impossible. Try it again,” he insisted.
The waitress tried again. And again. The card was declined each time. Stewart’s calm demeanor shifted to frustration. “This is ridiculous. Do you even know how to use the machine?” he snapped.
Jess’s face burned with embarrassment as other diners started to glance over. “Maybe there’s a problem with the card. Do you have another one?” she suggested, trying to ease the tension.
Stewart’s frustration turned to anger. “You think I planned this? Just pay the bill, Jess,” he demanded.
“I told you I can’t afford this place,” Jess said firmly. “This was your idea, and Adam’s. He said you were well-off.”
The situation grew tense as the restaurant manager approached, looking serious. “We might need to involve the authorities if this isn’t resolved,” he said.
Feeling overwhelmed, Jess excused herself to the restroom, needing a moment to calm down. As she splashed water on her face, her phone buzzed with a text from Adam: “How’s it going?”
Jess stared at her phone, fuming. She took a deep breath and tried to steady her nerves. When she returned to the table, Stewart was still arguing with the waitress and the manager. A security guard was now present, warning that they might need to call the police if the issue wasn’t settled.
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 puzzled. “I don’t know. Adam set this up and said he’d put money in my account. Looks like he didn’t.”
Jess turned to the security guard. “Can we step outside? I’ll call someone to settle this.”
Outside, the cool night air did little to ease 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?” Jess demanded.
Adam’s voice was light and amused. “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!” Jess yelled.
“Alright, alright. I’m on my way,” Adam said, still sounding amused.
When Adam finally arrived, he was grinning from ear to ear. “Hey, folks. Problem with the bill?” he asked.
“This isn’t funny, Adam. You’ve humiliated me,” Jess snapped.
Adam shrugged nonchalantly. “I thought it would be fun. I’ll cover it. Chill out.”
A few moments later, Adam returned with a receipt. “There. All settled. Happy now?” he asked, still grinning.
Jess’s eyes were blazing. “You think this is a joke? You crossed a line,” she said sharply.
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 nudge on the arm. “Come on, Jess. It wasn’t that bad.”
Jess shook her head, frustrated. “You don’t get it, Adam. You went too far.”
As Adam walked away, Jess turned to Stewart. “I’m really 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 deeply betrayed by her brother and thinking about setting clearer boundaries in the future.
What would you have done in Jess’s situation? If you enjoyed this story, check out another one about a waitress who accidentally started texting a stranger, pretending to be someone else!
