“When Jess was set up on a date with Stewart, she had no idea it would turn into a disaster at a high-end restaurant. What started as a casual evening quickly spiraled out of control when Stewart’s credit card was declined, and the manager threatened to call the police.
It all began when Jess’s brother, Adam, enthusiastically suggested, ‘Jess, you’ve got to meet this guy, Stewart. He works with me—solid job, nice car, the whole package.’
Jess glanced up briefly from her laptop. ‘Another setup, Adam?’
‘No, really,’ Adam insisted. ‘He’s been asking about you. I think you two will hit it off.’
With a sigh, Jess agreed, though she couldn’t hide her skepticism. ‘Alright, but if this turns out to be a mess, you’re never setting me up again.’
‘Deal,’ Adam said with a grin. ‘You’ll thank me later.’
After hours of getting ready, Jess finally felt prepared, though her apartment looked like a whirlwind had passed through. Stewart arrived in a sleek, shiny sedan, and as Jess slid into the passenger seat, she was struck by the contrast between her nerves and the luxurious car.
‘Hi, Jess,’ Stewart greeted her warmly. ‘Nice to meet you.’
‘Nice to meet you too, Stewart,’ Jess replied, still adjusting to the upscale setting Stewart had chosen.
The restaurant was the epitome of luxury, and Jess couldn’t help but feel slightly out of place. Stewart, however, seemed perfectly at ease, leading her to their table with confidence.
‘Order whatever you like,’ Stewart said, noticing Jess’s hesitation over the pricey menu.
Relieved, Jess began to relax as the evening progressed. Stewart was charming and engaging, and Jess found herself enjoying his company more than she had expected.
But when the bill arrived, the atmosphere took a sharp turn. Stewart handed over his card, only for the waitress to return, looking uneasy. ‘I’m sorry, sir, but your card has been declined.’
Stewart’s face tightened with frustration. ‘That can’t be right. Try it again.’
The card was declined once more. Stewart’s frustration turned into irritation. ‘This is ridiculous!’
The situation grew increasingly tense as the manager approached, and the other diners began to notice the commotion. Jess, embarrassed, suggested, ‘Maybe there’s an issue with the card. Do you have another one?’
Stewart’s irritation turned to desperation. ‘Just pay the bill, Jess.’
‘I told you I can’t afford this place,’ Jess replied, her patience wearing thin. ‘This was your idea. Adam said you had this covered.’
The tension was palpable, and Jess excused herself to the restroom to regroup. As she splashed water on her face, her phone buzzed with a message from Adam: ‘How’s it going?’
Jess was livid. When she returned, Stewart was still arguing with the staff. The situation had escalated to the point where a security guard was now involved.
Stewart looked at Jess, desperation in his eyes. ‘Can you help out? Just this once?’
‘I can’t,’ Jess replied firmly. ‘I don’t have that kind of money.’
Another message from Adam popped up on her phone: ‘How’s the date going, Sis? ;)’
Jess showed Stewart the text. ‘Did Adam know you couldn’t pay?’
Stewart looked bewildered. ‘I don’t know. Adam set this up. He said he’d transfer some money, but it looks like he didn’t.’
Feeling trapped, Jess turned to the security guard. ‘Can we step outside? I’ll call someone to settle this.’
Outside, Jess called Adam, barely containing her anger. ‘Adam, Stewart can’t pay the bill. What did you do?’
Adam chuckled. ‘Relax, Jess. Just use your card if you have to. It’s just a bit of fun.’
‘This isn’t funny, Adam. Get down here and fix it, now!’
When Adam finally arrived, still grinning, Jess was furious. ‘You’ve humiliated me,’ she snapped.
Adam shrugged it off. ‘I thought it would be fun. It’s all settled now, anyway. No big deal.’
But for Jess, it was a big deal. ‘You crossed a line, Adam. This wasn’t funny.’
As Adam walked away, still treating the situation lightly, Jess apologized to Stewart. ‘I’m sorry about tonight. I didn’t expect any of this.’
‘It’s okay,’ Stewart replied quietly, understanding in his eyes.
They parted ways, and as Jess walked home, she felt a deep sense of betrayal. She knew she needed to set new boundaries with her brother, starting with never letting him set her up on a date again.
What would you have done in Jess’s situation? If you enjoyed this story, here’s another one about a waitress who found herself in an unexpected texting exchange with a stranger.”
