When Jess agreed to go on a date with Stewart, she never imagined how badly things would go. What started as a casual evening turned into a complete disaster when Stewart’s credit card was declined at a fancy restaurant, and the manager threatened to call the police.
It all began when Jess’s brother, Adam, tried to set her up again.
“Jess, you gotta meet this guy,” Adam said, lounging on the couch while flipping through TV channels. “Stewart. He works with me. Real stand-up guy. Stable job, nice car—the whole package.”
Jess looked up from her laptop, skeptical. “Who is this Stewart?”
Adam leaned forward, his face serious. “He’s a great guy. Trust me, you’ll like him.”
Jess rolled her eyes. “Another setup? Really?”
Adam grinned. “This time is different, I promise. He’s been asking about you. I think you two will hit it off.”
Jess sighed. “Fine. But if this turns out to be another disaster, I’m never listening to you again.”
Adam chuckled. “Deal. You’ll thank me later.”
After spending hours getting ready, Jess’s apartment looked like a tornado had hit it. Despite her doubts, Adam’s insistence had convinced her to give it a chance. Soon, Stewart arrived in a shiny, new sedan that smelled like fresh leather. Jess climbed into the passenger seat, feeling a mix of excitement and nerves.
“Hey, Jess,” Stewart greeted her with a big smile. “Nice to meet you.”
“Nice to meet you too, Stewart,” she replied, trying to hide her nervousness.
“I thought we’d go to this new place downtown. It’s fancy, but the food’s incredible,” Stewart said, sounding confident.
“Sounds good,” Jess agreed, surprised but willing to go along.
The restaurant was very upscale, with elegant decorations and soft lighting. Jess felt a bit out of place, but Stewart seemed completely at home. He led her to their table, acting cool and confident.
“Order whatever you like,” he said, noticing Jess hesitating over the pricey menu.
“Thanks,” Jess replied, feeling a bit more relaxed. The evening started off well, with Stewart being charming and funny. 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 grin, but moments later, the waitress returned, looking uncomfortable. “I’m sorry, sir, but your card was declined.”
“That can’t be right. Try it again,” Stewart insisted, frowning.
The waitress swiped the card again. And again. It was still declined. Stewart’s smile faded, replaced by frustration. “This is ridiculous! You must be doing something wrong with the machine,” he snapped.
People at nearby tables started to stare, and Jess felt her face getting hot with embarrassment. She leaned in, trying to calm things down. “Maybe there’s an issue with the card. Do you have another one?”
Stewart’s frustration quickly turned into anger. “Do you think I planned this? Just pay the bill, Jess,” he demanded.
Jess’s eyes widened. “I told you I can’t afford this place. This was your idea! Adam said you were doing well.”
The tension grew as the restaurant manager approached, warning that he would have to involve the police if the bill wasn’t paid. Jess excused herself and headed to the restroom, needing a moment to breathe. Her phone buzzed with a text from Adam: “How’s it going?”
Jess stared at her phone, fuming. She splashed water on her face, trying to steady herself. When she came back, Stewart was still arguing with the waitress and the manager, and now a security guard had joined them, looking ready to call the police.
Stewart turned to Jess, his eyes pleading. “Can you help me out? Just this once?”
“I can’t,” Jess replied firmly. “I don’t have that kind of money.”
Her phone buzzed again. Another message from Adam: “How’s the date going, sis? ;)”
Jess showed the text to Stewart. “Did Adam know you couldn’t pay?”
Stewart looked puzzled. “I don’t know. Adam set this up. He said he’d put money in my account. But it 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 little to calm the tension. The security guard kept a close watch on them while Jess called Adam, her voice shaking with anger.
“Adam, Stewart can’t pay the bill. It’s huge! What have you done?”
Adam laughed. “Relax, Jess. Just trying to add a bit of excitement. Use your card if you have to.”
“Are you serious? Get down here and fix this mess!”
“Alright, alright. I’m coming,” Adam said, still chuckling.
When Adam arrived, he was still grinning like he’d pulled off the funniest joke ever. “Hey, folks. Problem with the bill?”
“This isn’t funny, Adam. You’ve embarrassed me,” Jess snapped.
Adam just shrugged. “I thought it’d be a fun surprise. I’ll pay. Relax.”
A few minutes later, Adam came back with a receipt in his hand. “There, all sorted. Happy now?”
Jess’s face flushed with anger. “You think this is a joke? You’ve crossed a line.”
Adam seemed unfazed. “Come on, it was just a prank. I wanted to spice things up.”
Stewart looked from Jess to Adam, clearly uncomfortable. “I’m really sorry. I didn’t know this would happen.”
Jess sighed. “It’s not your fault,” she said, turning back to her brother.
Adam, still smirking, gave Jess a light punch on the arm. “Don’t be so serious, Jess. It wasn’t that bad.”
Jess shook her head, her patience wearing thin. “You don’t understand, Adam. This wasn’t funny. 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 get it.”
They shared a moment of silent understanding before going their separate ways. Jess walked home, feeling hurt and betrayed by her brother, realizing she needed to set some new boundaries with him.
What would you do if you were in Jess’s shoes? If you enjoyed this story, here’s another one about a waitress who got caught up in a texting mix-up with a stranger!
