I Went on a Date with My Brother’s Friend – Turned out It Was a Trap

Jess’s date with Stewart quickly went from promising to a full-blown disaster. What was supposed to be a simple night out turned into a nightmare at a posh restaurant when Stewart’s credit card was declined, and the manager threatened to call the police.

It all started with Jess’s brother, Adam, trying to set her up 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—great guy, stable job, nice car, the whole deal.”

Jess barely looked up from her laptop. “Who’s this guy?”

“Stewart,” Adam repeated, a bit annoyed. “Trust me, he’s different. You’ll like him.”

“Another setup?” Jess asked, raising an eyebrow.

“No, seriously. He’s asking about you. I think you two will hit it off.”

Jess sighed. “Alright, but if this turns into another disaster, I’m done listening to you.”

“Deal. You’ll thank me later,” Adam said with a smirk.

After hours of getting ready, Jess’s apartment looked like a tornado had hit it. But Adam’s encouragement convinced her to give it a shot. Stewart arrived in a shiny, new sedan that smelled like leather. Jess slid into the passenger seat, trying to ignore her nerves as the engine hummed smoothly beneath her.

“Hey, Jess,” Stewart greeted with a warm smile. “Nice to meet you.”

“Nice to meet you too, Stewart,” Jess replied, trying to sound enthusiastic.

“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 luxury haven with sparkling chandeliers and white tablecloths. Jess felt like she didn’t belong, but Stewart seemed perfectly at ease. He led her to their table with charm and confidence.

“Order whatever you like,” Stewart said, waving away Jess’s hesitation about the pricey menu.

“Thanks,” Jess said, feeling slightly relieved. The evening started off well. Stewart was charming, and Jess found herself laughing more than she had in a while.

Then the bill arrived.

Stewart handed over his credit card with a flourish, but the waitress soon returned, looking uneasy. “I’m sorry, sir, but your card was declined.”

“That’s impossible,” Stewart said, his face turning red. “Try it again.”

The card was declined again. And again. Stewart’s calm demeanor shifted to frustration. “This is ridiculous. Do you even know how to use the machine?” he snapped.

Other diners started to glance over, and Jess’s face burned with embarrassment. “Maybe there’s a problem with the card. Do you have another one?” she asked, trying to calm the situation.

Stewart’s frustration boiled over into anger. “You think I planned this? Just pay the bill, Jess.”

“I told you I can’t afford this place,” Jess replied, her voice firm. “This was your idea, and Adam’s. He said you were well-off.”

The tension grew as the manager approached, looking serious. “We might have to involve the authorities if this isn’t resolved,” he said.

Jess excused herself to the restroom, needing a moment to regroup. Her phone buzzed with a text from Adam: “How’s it going?”

Jess stared at her phone, fuming. She splashed water on her face and tried to calm down. When she returned, Stewart was still arguing with the waitress and the manager. A security guard had now joined, warning that the police might be called if the bill wasn’t paid.

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. “Please, can we step outside? I’ll call someone to sort this out.”

Outside, the cool night air did little to ease the tension. The security guard watched them closely as Jess called Adam, her anger barely contained.

“Adam, Stewart can’t pay the bill. It’s huge! What did you do?”

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!”

“Alright, alright. I’m on my way,” Adam said, still sounding amused.

When Adam 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. “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 punch 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 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!