When Jess agreed to go on a date with Stewart, she had no idea what kind of chaos was waiting for her. What was supposed to be a nice, casual evening quickly turned into a nightmare at a fancy restaurant. It all started when Stewart’s credit card got declined, and things went from bad to worse when the manager threatened to call the police.
It all began with Adam, Jess’s brother, who couldn’t help but try to set her up again.
“Jess, you gotta meet this guy,” Adam said, sprawled out on the couch, lazily flipping through TV channels. “Stewart. Works with me. Real stand-up guy. Stable job, nice car—the whole deal.”
Jess barely looked up from her laptop. “Who’s this guy?”
“Stewart,” Adam repeated, trying to sound convincing. “Trust me, he’s different. You’ll like him.”
“Another setup?” Jess groaned, rolling her eyes. She had been through enough of Adam’s matchmaking attempts.
“No, seriously. He’s been asking about you. I think you two will hit it off,” Adam insisted.
Jess sighed, not buying it. “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 grin.
Jess spent hours getting ready. Clothes were scattered everywhere in her apartment, making it look like a tornado had blown through. But Adam had been so insistent that she decided to give it a shot. When Stewart arrived, Jess was surprised to see him in a sleek, shiny new car that smelled like fresh leather.
She slipped into the passenger seat, feeling the smooth leather under her and hearing the quiet hum of the engine.
“Hey, Jess,” Stewart greeted her with a warm smile. “Nice to meet you.”
“Nice to meet you, Stewart,” she replied, trying to sound relaxed.
“I thought we’d go to this new place downtown,” Stewart said confidently. “It’s fancy, but the food’s incredible.”
“Sounds good,” Jess replied, trying to hide her surprise. She hadn’t expected a fancy place.
The restaurant was absolutely luxurious, with sparkling chandeliers, white tablecloths, and waiters in tuxedos. Jess felt a bit out of place, but Stewart seemed completely at ease. He led her to their table like he was used to places like this.
“Order whatever you like,” Stewart said casually, noticing Jess’s hesitation as she looked at the expensive menu.
“Thanks,” Jess said, feeling a little more comfortable. The evening started off well. Stewart was charming, funny, and seemed genuinely interested in her. Jess found herself laughing more than she had in a long time.
But then the bill arrived.
Stewart handed over his credit card with a flourish, looking confident. But a few moments later, the waitress returned, looking nervous. “I’m sorry, sir, but your card was declined.”
Stewart blinked in surprise. “That’s impossible. Try it again,” he said, frowning.
The waitress tried again. And again. The card was declined each time. Stewart’s expression shifted from calm and collected to frustrated and annoyed. “This is ridiculous! Do you even know how to use the machine?” he snapped.
Jess felt her cheeks flush with embarrassment as she noticed other diners starting to look over. “Maybe there’s a problem with the card. Do you have another one?” she suggested gently, trying to calm things down.
Stewart’s face turned red with anger. “You think I planned this? Just pay the bill, Jess,” he demanded.
Jess stared at him in disbelief. “I told you I can’t afford this place,” she replied firmly. “This was your idea. Adam told me you were doing well.”
The tension grew thicker as the restaurant manager walked over, looking stern. “Is there a problem here?” he asked, his tone implying he was ready to involve the authorities if needed.
Feeling overwhelmed, Jess excused herself and hurried to the restroom, needing a moment to collect herself. As she splashed cold water on her face, her phone buzzed with a text from Adam: “How’s it going?”
Jess stared at her phone, feeling a mix of anger and frustration. She took a deep breath, trying to calm down. When she returned to the table, Stewart was still arguing with the waitress and the manager. A security guard was now standing nearby, warning that they might need to call the police if the bill wasn’t settled.
Stewart turned to Jess, looking desperate. “Can you help out? Just this once?”
Jess shook her head, feeling trapped. “I can’t. I don’t have that kind of money.”
Her phone buzzed again. Another message from Adam: “How’s the date going there, Sister? ;)”
Jess held up the phone to show Stewart. “Did Adam know you couldn’t pay?”
Stewart looked genuinely confused. “I don’t know. Adam set this whole thing up. He said he’d put money in my account, but it looks like he didn’t.”
Jess turned to the security guard. “Can we step outside, please? I’ll call someone to settle this.”
The guard nodded, and they moved outside. The cool night air did little to calm Jess’s nerves. The guard kept a close watch on them while Jess called Adam, her anger boiling over.
“Adam, Stewart can’t pay the bill. It’s huge! What did you do?” she snapped.
Adam chuckled on the other end. “Relax, Jess. Just adding a bit of excitement. Use your card if you have to.”
“Are you serious?” Jess shouted. “Get down here and fix this mess, now!”
“Alright, alright. I’m on my way,” Adam replied, still sounding amused.
When Adam finally showed up, he was still grinning like he found the whole thing hilarious. “Hey, folks. Problem with the bill?” he asked, pretending to be surprised.
“This isn’t funny, Adam. You’ve humiliated me,” Jess said angrily.
Adam shrugged. “I thought it would be fun. Don’t worry, I’ll cover it. Chill out.”
A few minutes later, Adam came back with a receipt. “There you go. All sorted. Happy now?” he asked, still smirking.
Jess’s eyes blazed with anger. “You think this is a joke? You went way too far,” she snapped.
Adam didn’t seem bothered at all. “Come on, it was just a prank. I wanted to spice things up a bit.”
Stewart looked at Jess and then at Adam, clearly uncomfortable. “I’m really sorry, Jess. I had no idea this would happen.”
Jess sighed, turning to Stewart. “It’s not your fault,” she said quietly, still glaring at her brother.
Adam, still trying to lighten the mood, gave Jess a playful nudge on the arm. “Come on, Jess. It wasn’t that bad.”
Jess shook her head, fed up with his attitude. “You don’t get it, Adam. You went too far.”
As Adam walked away, Jess turned back to Stewart. “I’m really sorry about tonight. I didn’t expect any of this.”
“It’s okay,” Stewart replied softly. “I understand.”
They shared a moment of quiet understanding before they parted ways. As Jess walked home, she felt hurt and betrayed by her brother. She realized she needed to set some serious boundaries with him from now on.
What would you have done if you were Jess? If you liked this story, there’s another one about a waitress who accidentally started texting with a stranger, pretending to be someone else!
