I Went on a Date with My Brother’s Friend – It Was a Setup

My brother recently arranged for me to go on a date with his friend Stewart, which ended up being a disaster. We found ourselves stuck at a fancy restaurant with an unpaid bill, and as the manager threatened to call the police, I realized the extent of Adam’s plan. I was left wondering how we were going to get out of this mess.

“You need to meet this guy, Jess,” Adam said, his face lit up as if he had just discovered something amazing. He was comfortably settled on my couch, channel surfing.

“Who are you talking about?” I asked, still focused on my laptop.

“Stewart. He works with me. He’s a great guy. Solid job, nice car, the whole package.”

I rolled my eyes. “Is this another one of your setups?”

“No, seriously! He’s different. You’ll really like him. And he’s been asking about you.”

I sighed, skeptical due to Adam’s bad track record with setups, but his enthusiasm about Stewart made me curious. “Alright, but if this goes poorly, I’m not going to trust your setups anymore.”

Adam smirked. “Deal. You’ll thank me later, trust me.”

I spent the next few hours preparing carefully, wanting to make a good impression despite my reservations. By the time I was ready, my apartment was a mess from all the makeup and clothes. Despite my anxiety, Adam’s encouragement kept me going.

Stewart arrived in a shiny new sedan. As I got in, I couldn’t help but notice the car’s clean leather smell and the smooth hum of the engine.

“Hi, Jess?” he greeted me with a genuinely warm smile.

“Yes, that’s me. Nice to meet you, Stewart.”

“Likewise. You look great, by the way.”

I blushed, feeling a bit more at ease. “Thanks. So, where are we heading?”

“I thought we could try this new place downtown. It’s fancy, but the food is amazing.”

“Sounds good,” I replied, surprised by the upscale choice.

The restaurant was like something out of a movie, luxurious yet understated. I felt a bit underdressed in my chosen outfit. Stewart seemed perfectly comfortable, chatting easily with the host and leading me to our table.

“This place is stunning,” I remarked, looking around.

“Only the best,” he said with a wink. “Order whatever you like.”

The menu was shockingly pricey, but Stewart dismissed my hesitation. “Don’t worry, it’s on me.”

I smiled, feeling grateful and flattered. Our conversation flowed smoothly. Stewart was charming, funny, and intelligent. I laughed more than I had in weeks.

The evening was great until the bill arrived. Stewart handed over his card with confidence, still in the middle of a joke. The waitress returned looking apologetic.

“I’m sorry, sir, but your card was declined.”

Stewart’s face fell. “That can’t be right. Try it again.”

She did. Twice more, with the same result. Stewart’s charm disappeared, replaced by frustration. “This is ridiculous. Do you even know how to use the machine?” he snapped.

People started to look our way. Embarrassed, I suggested, “Stewart, maybe there’s an issue with the card. Do you have another one?”

He glared at the waitress, then turned to me. “This never happens. Someone must have made a mistake.”

Stewart glanced at me sheepishly. “Do you have any cash on you?” he asked.

I was shocked. “I told you I can’t afford this place. I don’t have that kind of money!”

Stewart’s eyes flared with frustration. “Do you think I planned this? Please, just pay the bill, Jess.”

I folded my arms, standing firm. “No. I don’t have the money. This was your idea. And Adam’s, for that matter. He said you had a good job and lived the high life.”

The tension was palpable. The waitress looked uncomfortable, and the manager stood by her side.

Stewart’s face twisted with anger. “Unbelievable.”

Feeling humiliated, I muttered, “I’m going to the bathroom,” needing a moment to regroup.

Inside, I leaned against the sink, taking deep breaths. My phone buzzed. A message from Adam: “How’s it going?”

I stared at the screen, wondering how to explain the fiasco. I splashed water on my face, trying to calm myself. I had to face the situation.

Back at the table, I saw Stewart arguing with the waitress, the manager now involved. My heart pounded as I approached.

“Everything sorted out?” I asked, trying to stay calm.

Stewart turned to me, barely containing his anger. “They’re saying my card is no good. Can you believe this?”

Feeling desperate, I suggested, “Maybe we should just leave.”

“We can’t just run out without paying the bill,” he replied. “We’ll get caught for sure, and they’ll make an example of us.”

I shook my head. “Then we’re stuck.”

The manager stepped in. “Sir, we need to resolve this. Do you have another form of payment?”

Stewart looked at me, pleading. I shook my head firmly.

“We’ll have to figure something out,” he muttered, his confidence gone.

I had a bad feeling the night was far from over. Stewart started arguing with the security guard who had approached.

“I told you, there’s an issue with my card! Call my bank if you need to!”

“If you can’t pay, we’ll have to involve the authorities,” the guard warned sternly.

My heart sank. “Stewart, what are you going to do?”

“Jess, I didn’t expect this. Can you help out? Just this once?” he pleaded.

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

My phone buzzed again. A message from Adam: “How’s the date, Sis? ;)”

Furious, I showed Stewart the message. “Did Adam know you couldn’t pay for this?”

Stewart seemed genuinely confused. “I don’t know. He just set us up. But—”

“What about the car? How can you afford it? You need good credit for a car like that.”

He sighed, looking defeated. “Adam rented the car for me. He said it would impress you. He also said he’d put money in my account to cover the date, but apparently, he didn’t.”

Turning to the guard, I said, “Can we step outside? I need to make a call to resolve this.”

Outside, we stood in the cool night air, with the guard close by. I dialed Adam, my anger barely in check.

“Jess! How’s the date?”

“Adam, what did you do? Stewart can’t pay the bill! It’s huge. You said he was good for it. How could you set us up like this?”

He laughed. “Relax, Jess. Just adding some excitement. Use your card if you need to.”

“Are you kidding me? Get down here and fix this. Now.”

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

I hung up, furious. “He’s coming. Let’s wait.”

Stewart leaned against the wall, looking miserable. “I’m really sorry, Jess. I didn’t know he’d do this.”

I shrugged, exhausted. “It’s not your fault. My brother’s the idiot.”

Adam arrived, still grinning. “Hey, trouble with the bill?”

I glared at him. “This isn’t funny, Adam. You went too far. Why set us up like this? For fun?”

He waved dismissively. “Alright, I’ll pay. Relax.”

Adam walked in and came back with a receipt soon after. “All settled. Happy?”

“You think this is a joke? You humiliated me,” I snapped.

Adam shrugged. “Lighten up, Jess. It’s just a prank. I wanted to add some excitement to your life.”

Stewart apologized again. “I had no idea.”

“It’s okay, Stewart. This isn’t your fault,” I said, glaring at Adam.

Standing outside the restaurant, the night felt heavy and cold. The security guard watched us closely. Stewart shifted awkwardly. “I hope you can forgive me, Jess. I’d like to make it up to you.”

I nodded slowly. “Maybe. I just need time to think.”

Adam, still grinning, playfully punched my arm. “Come on, Jess. It wasn’t that bad.”

I shook my head. “You don’t get it, Adam. You crossed the line.”

As Adam walked away whistling, Stewart apologized quietly. “I’m sorry about tonight. I didn’t expect this.”

“It’s okay,” I said quietly. “I understand.”

We shared a moment of mutual disappointment. As we parted ways, I felt betrayed by my brother. Stewart, still regretful, watched me go.

“Goodnight, Jess,” he called.

“Goodnight, Stewart,” I replied, my voice tinged with regret.

As I walked home, I realized I needed to reassess my trust in my brother and those around me. Adam’s pranks had gone too far, and it was time to set some boundaries.

What would you have done?

Share