It all started with a seemingly innocent suggestion from Jess’s brother, Adam. He had been lounging on the couch, flipping through TV channels, when he suddenly said, “Jess, you’ve got to meet this guy. Stewart. He works with me. Great guy—stable job, nice car, the whole package.”

Jess, barely glancing up from her laptop, responded with skepticism, “Who’s this Stewart?”

“Trust me, he’s different. I think you’ll really like him,” Adam insisted.

With a sigh and an eye roll, Jess finally agreed to the setup, but not without a warning. “Alright, but if this turns out to be another disaster, I’m never listening to you again.”

Adam, confident as ever, smirked. “Deal. You’ll thank me later.”

The evening of the date arrived, and Jess found herself in a whirlwind of preparation. After what felt like hours of getting ready, her apartment looked like a tornado had hit, but Adam’s encouragement had her convinced to give it a try. When Stewart pulled up in a sleek, brand-new sedan, Jess was impressed. The car’s pristine condition and the quiet hum of its engine did little to calm her nerves, but she climbed in, hoping for the best.

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

“Nice to meet you too, Stewart,” she replied, trying to mask her apprehension.

“I thought we’d try this new place downtown. It’s fancy, but the food is amazing,” Stewart said, clearly excited about the evening.

“Sounds good,” Jess said, hiding her surprise at the upscale choice of venue.

The restaurant was a picture of luxury, and Jess couldn’t help but feel slightly out of place. Stewart, on the other hand, seemed completely at ease, leading her confidently to their table.

“Order whatever you like,” Stewart said, waving off her hesitation over the pricey menu.

With that, Jess started to relax. The evening began smoothly—Stewart was charming, engaging, and Jess found herself laughing more than she had in a long time. But the lighthearted mood shattered when the bill arrived.

Stewart handed his credit card to the waitress with a flourish, but moments later, she returned, looking uncomfortable. “I’m sorry, sir, but your card was declined.”

“That’s impossible. Try it again,” Stewart said, his tone more insistent.

When the card was declined again, Stewart’s demeanor shifted from charm to frustration. “This is ridiculous. Do you even know how to use the machine?” he snapped at the waitress.

Jess’s face flushed with embarrassment as she noticed the other diners starting to glance their way. Trying to calm the situation, she suggested, “Maybe there’s a problem with the card. Do you have another one?”

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

Jess was taken aback. “I told you I couldn’t afford this place,” she said firmly. “This was your idea, and Adam’s. He said you were well-off.”

The tension at the table was unbearable, and when the manager joined in, threatening to call the police, Jess excused herself to the restroom to collect her thoughts. As she splashed water on her face, her phone buzzed with a text from Adam: “How’s it going?”

Jess stared at the screen, fuming. When she returned, Stewart was still arguing with the manager, and now a security guard was involved, warning them that the police might need to be called.

“Can you help out? Just this once?” Stewart asked, looking desperate.

“I can’t. I don’t have that kind of money,” Jess replied, feeling increasingly trapped.

Her phone buzzed again—another text from Adam: “How’s the date going there, Sister? ;)”

Jess showed Stewart the message. “Did Adam know you couldn’t pay?”

Stewart looked confused. “I don’t know. Adam set this up and said he’d put money in my account. Looks like he didn’t.”

Feeling betrayed, Jess asked the security guard if they could step outside while she called someone to settle the bill. Outside, the cool night air did little to ease her anger as she called Adam.

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

Adam laughed. “Relax, Jess. Just adding a bit of excitement. Use your card if you have to.”

“You’re kidding, right? Get down here and fix this mess!” Jess demanded.

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

When Adam arrived, he was grinning like it was all a big joke. “Hey, folks. Problem with the bill?”

Jess was furious. “This isn’t funny, Adam. You’ve humiliated me.”

Adam shrugged it off. “I thought it would be fun. I’ll cover it. Chill out.”

Moments later, Adam returned with the receipt. “There. All settled. Happy now?”

Jess was livid. “You think this is a joke? You crossed a line.”

But Adam remained 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, but her gaze was fixed on her brother.

Adam, still grinning, gave Jess a playful nudge. “Come on, Jess. It wasn’t that bad.”

But Jess shook her head. “You don’t get it, Adam. You went too far.”

As Adam walked away, Jess turned to Stewart, apologizing for the disaster of an evening. “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 thinking about the new boundaries she needed to set in the future.