My brother Adam’s latest matchmaking attempt landed me on a date with his friend, Stewart, and it turned into a total fiasco. Stuck at a fancy restaurant, we were faced with an unpaid bill as tensions escalated and the manager threatened to call the police. I couldn’t believe how far Adam had gone, leaving me to wonder how we’d escape this mess.

“Jess, you gotta meet this guy,” Adam grinned, lounging on my couch. “Stewart’s a stand-up guy—stable job, nice car, the works.” Despite my skepticism, I agreed to give him a chance, only to regret it later as I spent hours preparing for the date.

Stewart arrived in a shiny sedan, looking impressive, and the evening started well. The restaurant was upscale, and our conversation flowed easily. But when the bill came, Stewart’s card was declined—not once, but three times. As his charm evaporated, embarrassment washed over me. “Do you have any cash?” he asked, and my heart sank. I didn’t.

As the situation spiraled, Stewart argued with the security guard while I stepped outside to call Adam. When I confronted him about the mess he created, he laughed it off as a prank. Furious, I realized that I needed to reassess my trust in my brother and set some boundaries. As I left, Stewart’s apologetic gaze lingered, leaving me with mixed feelings of disappointment and regret.