I Went on a Date with My Brother’s Friend – Then I Realized It Was All a Setup!

My brother’s latest matchmaking attempt turned into a disaster when his friend, Stewart, took me on a date that ended with us stuck at a fancy restaurant with no way to pay the bill. As the situation got worse and the manager threatened to call the police, I started wondering how much trouble Adam had dragged me into—and how we were going to get out of it.

A few weeks ago, Adam introduced me to his friend, Stewart. He told me Stewart was a great guy—someone with a good job, his own house, and a nice car.

I was curious and decided to give it a try. Stewart picked me up one evening, and we went to a super fancy restaurant. It was the kind of place I’d never thought I’d go to. Even the coffee was crazy expensive—around $100 a cup!

Looking at the menu, I told him honestly that I couldn’t afford to eat there. Stewart just smiled and said, “I’ve got this. Please don’t say no, or you’ll hurt my feelings.” I felt flattered and didn’t want to argue, so I agreed.

We ordered our food, and everything seemed to go smoothly. Stewart was funny, charming, and full of interesting stories. We talked about all sorts of things, and I was actually enjoying the evening.

Then the bill came. Stewart confidently handed his card to the waitress. I excused myself to use the bathroom, but when I came back, everything had changed. Even now, it still feels like a bad dream.

“Is everything okay?” I asked, trying to stay calm even though I was getting nervous.

Stewart looked frustrated. “They’re saying my card isn’t working. Can you believe this?”

I hesitated, unsure what to do. “Maybe we should… leave quietly?” I whispered.

“What? Walk out without paying? Are you serious? The security guard will stop us in seconds,” he said, glancing toward the entrance.

Before we could figure anything out, the manager walked over. “Sir, we need to settle the payment. Do you have another way to pay?” he asked, staying polite but firm.

Stewart turned to me, his eyes pleading. I shook my head. “I can’t help you,” I whispered.

He sighed and rubbed his forehead. “Fine. We’ll figure something out,” he muttered, but his earlier confidence was gone.

Then, things got even worse. A security guard approached, his large figure looming over us. Stewart started getting annoyed.

“I told you there’s an issue with my card! Call my bank if you don’t believe me!” Stewart snapped, his voice getting louder.

“Sir, if you can’t pay, we’ll have to call the police,” the guard said, leaving no room for argument.

At that moment, my phone buzzed. It was a text from Adam: “How’s the date going, Sis? ;)”

Anger boiled inside me. I showed the message to Stewart. “Did Adam know you couldn’t afford this?”

Stewart looked genuinely shocked. “I—I don’t know. He set us up, but—”

I cut him off, narrowing my eyes. “What about the car outside? How are you driving something like that if you’re broke? That car requires good credit.”

Stewart sighed, shoulders slumping. “Adam rented it for me,” he admitted. “He thought it would impress you. He also said he’d send me money to pay for dinner, but… I guess he never did.”

I turned to the security guard and spoke calmly, “Sir, can we step outside? I’ll make a call to fix this.”

Once outside, I immediately called Adam, trying to control my frustration.

“Adam, what is going on? Stewart can’t pay! You told me he could! How could you set me up like this?”

Adam just laughed. “Relax, Jess. I was just making your night a little more interesting. Use your card if you have to.”

I clenched my jaw. “Are you serious right now? Get over here and fix this. I’m not kidding.”

“Alright, alright. No need to freak out. I’m coming,” he said, still chuckling.

Next to me, Stewart leaned against the wall, his face pale. “Jess, I’m really sorry. I had no idea Adam would do this.”

I sighed, shaking my head. “It’s not your fault, Stewart. My brother is just… unbelievable.”

When Adam finally arrived, he had a smug look on his face. “What’s the problem? Something wrong with the bill?”

I glared at him. “This isn’t funny, Adam. You went too far. Was this a joke to you? You set us up for fun, and that’s not okay.”

He waved me off like it was no big deal. “Fine, fine. I’ll take care of it. Chill out.”

Stewart looked between us, clearly uncomfortable. “Jess, I’m really sorry. I didn’t know this would happen.”

“It’s not your fault, Stewart,” I said firmly, shooting another glare at Adam.

We stood outside in the chilly night, the weight of everything settling in. Stewart shifted awkwardly. “I hope you can forgive me, Jess. I really want to make it up to you.”

I took a deep breath, trying to let go of my frustration. “Maybe. I just need some time to think.”

There was a moment of silence, the disappointment heavy between us. As we got ready to leave, I felt a little sad.

“Goodnight, Jess,” Stewart said quietly, regret in his voice.

“Goodnight, Stewart,” I replied, feeling exhausted.

As I walked home, the cold night air felt heavier than usual. I realized I needed to rethink the trust I put in the people around me. Adam had gone too far, and it was time to set some clear boundaries—not just for him, but for myself.