I Went on a Date with My Brothers Friend – Turned out It Was a Trap

My brothers latest setup landed me on a disastrous date with his friend, Stewart, and we were stuck at a swanky restaurant with an unpaid bill. As tensions escalated and the manager threatened to call the police, I realized just how far Adam had gone, leaving me to wonder how wed escape.

“Jess, you gotta meet this guy,” Adam said, grinning like he had just discovered the secret to eternal youth. He lounged on my couch, flipping through channels.

Adam lounging in the living room | Source: Pexels

“Whos this guy?” I asked, not looking up from my laptop.

“Stewart. Works with me. Real stand-up guy. Stable job, nice car, the works.”

I rolled my eyes. “Another one of your brilliant setups?”

“No, seriously! Hes different. Youll like him. Plus, hes been asking about you.”

I sighed. Adams track record with setting me up was abysmal, but the way he spoke about Stewart piqued my curiosity. “Fine. But if he turns out to be another dud, Im never listening to you again.”

Jess deciding to give Stewart a chance despite her doubts | Source: Pexels

Adam smirked. “Deal. Youll thank me later.”

I spent the next few hours meticulously getting ready, wanting to make a good impression despite my reservations. By the time I was done, my apartment looked like a war zone of makeup and clothes. My nerves were on edge, but Adams encouragement kept me on target.

Stewart picked me up in a shiny sedan that looked like it had just rolled off the showroom floor. As I slid into the passenger seat, I couldnt help but notice the clean, leather smell and the subtle hum of the engine.

Stewarts shiny sedan parked outside Jesss apartment | Source: Pexels

“Hey, Jess, right?” he said with a smile that seemed genuinely warm.

“Yep, thats 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 headed?”

“Thought Id take you to this new place downtown. Fancy, but the food is incredible.”

“Sounds good,” I replied, trying to hide my surprise. I wasnt used to such upscale outings.

Jess and Stewart at the upscale restaurant | Source: Pexels

The restaurant was like something out of a movie, with charming, low-key decor, but oozing luxury. I felt underdressed in my carefully chosen outfit. Stewart seemed completely at home, though, chatting easily with the host and leading me to our table.

“This place is amazing,” I said, looking around in awe.

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

The menu made my eyes widen. Everything was outrageously expensive, but Stewart waved off my hesitation. “Dont worry, its on me.”

The elegant restaurant interior | Source: Pexels

I smiled, grateful and flattered. Our conversation flowed effortlessly. Stewart was charming, funny, and intelligent. I found myself laughing more than I had in weeks.

The evening was perfect until the bill arrived. Stewart handed over his card with a confident flourish, still in the middle of a joke. The waitress returned, her expression uneasy.

“Im sorry, sir, but your card was declined.”

Stewarts face dropped. “That cant be right. Try it again.”

Stewart presents his credit card to pay for the meal | Source: Midjourney

She did. Twice more, with the same result. Stewarts charm evaporated, replaced by a scowl. “This is ridiculous. Do you even know how to use the machine?” he snapped.

Other diners began to glance our way. I felt my face burn with embarrassment. “Stewart, maybe theres a problem with the card. Do you have another one?” I suggested, trying to defuse the situation.

He glared at the waitress, then turned to me. “I swear this never happens. Someone must have screwed something up.”

The waitress inspecting Stewarts declined card | Source: Pexels

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

I was taken aback. “I told you I cant afford this place. I dont have this kind of money!”

Stewarts eyes flashed with anger. “You think I planned this? Please, just pay the bill, Jess.”

I crossed my arms, standing firm. “No. I dont have the money. This was your idea. And Adams, I should add. He said you had a good job and lived the high life.”

The tension at the table was thick. I could see the waitress shifting uncomfortably, the manager now standing by her side.

Stewarts face twisted in frustration. “Unbelievable.”

Jess stands up angrily, refusing to pay the bill | Source: Midjourney

I felt angry and humiliated. “Im going to the bathroom,” I muttered, needing a moment to collect myself.

Inside, I leaned against the sink, taking deep breaths. My phone buzzed in my purse. A text from Adam: “Hows it going?”

I stared at the screen, debating whether to reply. How could I explain this disaster? I splashed water on my face and tried to steady my nerves. I had to go back out there and face the music.

Jess reads the text message from her brother in the restroom | Source: Pexels

Stepping back into the dining area, I could see Stewart still arguing with the waitress. The manager was now involved, and the tension was palpable. I walked back to the table, my heart pounding.

“Everything alright now?” I asked, my voice steadier than I felt.

Stewart turned to me, his anger barely contained. “Theyre saying my cards no good. Can you believe this?”

I swallowed hard. “Maybe we should just leave.”

“What? Just run out without paying the bill?” he muttered. “We cant do that. Look at their security guard, hell catch us for sure. And this looks like the sort of place thatll press charges to make an example of us.”

I shook my head. “Then were stuck.”

Stewart and Jess discussing their options as the situation worsens | Source: Midjourney

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

Stewart looked at me, desperation in his eyes. I shook my head firmly.

“I guess well have to figure something out,” he muttered, his bravado completely gone.

I couldnt shake the feeling that the night was far from over, and not in a good way. Sure enough, Stewart started a heated argument with the restaurants security guard when he stepped over. Stewarts face was red, and his voice was rising with each utterance.

The restaurants security guard getting involved | Source: Pexels

“I told you, theres a mistake with my card! Call my bank if you have to!”

“Sir, if you cant pay, well have to involve the authorities,” the swarthy security guard warned sternly.

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

He turned to me, desperation in his eyes. “Jess, I didnt expect this. Can you help out? Just this once?”

“I cant. I already told you I dont have that kind of money,” I replied, feeling trapped and humiliated.

As if on cue, my phone buzzed. A message from Adam: “Hows the date going there, Sister? ;)”

Stewart arguing with the security guard while the manager looks on | Source: Midjourney

I felt a surge of anger. I showed Stewart the message. “Did Adam know that you couldnt afford all this?”

Stewart looked genuinely confused. “Well, I dont know. He just set us up. But — “

“Whats with the car then? How can you afford it? You need good credit to drive a car like that.”

He sighed, looking defeated. “Adam hired the car for me. Said it would impress you. He also said hed put money into my bank account to cover the date, but now Im realizing he never did.”

Jess showing Stewart the text from Adam | Source: Pexels

I turned to the security guard. “Sir, please can we step outside to avoid disrupting the other diners further? Ill make a call for someone to come and settle the bill.”

Outside the restaurant, the night air was cool and biting. The security guard followed us, standing a few feet away to ensure we didnt run off. I dialed Adam, my anger barely in check.

“Jess! Hows the date?”

“Adam, what the heck did you do? Stewart cant pay the bill! Its huge. You said he was good for it. How could you do this to me?”

He chuckled. “Relax, Jess. Just spicing up your life a bit. Use your card if you have to.”

Jess looking askance at Stewart while the security guard watches them | Source: Midjourney

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

“Alright, alright. Dont blow a gasket. Im on my way,” he said, still laughing.

I hung up, seething. “Hes coming. Lets wait.”

Stewart leaned against the wall, looking miserable. “Im really sorry, Jess. I didnt know hed pull something like this.”

I shrugged, feeling angry and exhausted. “Its not your fault. My brothers an idiot.”

Jess and Stewart having a frank discussion outside the restaurant | Source: Midjourney

Adam arrived, his smug grin making me want to scream. “Hey, folks. Problem with the bill?”

I glared at him. “This isnt funny, Adam. You went too far. Why did you set this trap for us? For your own amusement? Its totally unacceptable.”

He waved his hand dismissively. “Alright, alright. Ill pay. Relax.”

Adam sauntered in, and moments later, returned with a receipt. “There. All settled. Happy now?”

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

Adam shrugged. “Lighten up, Jess. It was just a prank. I wanted to spice your lives up a little, give you guys an adventure.”

Stewart looked at Adam, then at me. “Im really sorry. I had no idea.”

“Its okay, Stewart. This isnt on you,” I said, glaring at my brother.

Adam arriving with a laugh, ready to rescue the situation | Source: Midjourney

We stood outside the restaurant, the night now feeling heavy and cold. The security guard watched us closely. Stewart shifted awkwardly. “I hope you can forgive me, Jess. Id like to make it up to you.”

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

Adam, still grinning, gave me a playful punch on the arm. “Come on, Jess. It wasnt that bad.”

I shook my head. “You dont get it, Adam. Youve crossed a line.”

Jess and Stewart sharing a moment of understanding | Source: Midjourney

As Adam walked away, whistling, I turned to Stewart. “Im sorry about tonight. I didnt expect any of this.”

“Its okay,” he said quietly. “I get it.”

We shared a moment of understanding, a silent acknowledgment of the disappointment we both felt. As we parted ways, I betrayed by my brother. Stewart, still apologetic, watched me go.

“Goodnight, Jess,” he called after me.

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

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

Jess walking home, deep in thought about setting new boundaries with her brother | Source: Midjourney

What would you have done? If you enjoyed this story, heres another one for you about a waitress who texted with a stranger, posing as a woman hed met there before.

This work is inspired by real events and people, but it has been fictionalized for creative purposes. Names, characters, and details have been changed to protect privacy and enhance the narrative. Any resemblance to actual persons, living or dead, or actual events is purely coincidental and not intended by the author.

The author and publisher make no claims to the accuracy of events or the portrayal of characters and are not liable for any misinterpretation. This story is provided “as is,” and any opinions expressed are those of the characters and do not reflect the views of the author or publisher.

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