On our first date, we went to a classy restaurant. As soon as we sat down, she smiled at the waiter and asked, “What’s the most expensive dish on your menu?” My heart sank.

I was ready to pay for dinner, but I hadn’t planned for a meal that would leave me broke. The waiter froze, glanced at me, and then carefully described a lavish seafood platter that cost more than my monthly grocery bill. I forced a smile, trying to hide my shock, and told him to give us a moment to decide. In that instant, I started to wonder if I’d made a huge mistake.

As we looked over the menu, I gently asked if she really wanted that dish. To my surprise, she laughed and said, “Oh no, I’m just curious. I always ask that on first dates—it tells me a lot about the person I’m with.” Relief washed over me, but curiosity replaced it. She explained, “If someone insists on ordering it, it shows they care more about appearances than about us having a good time. If they react with anger or stress, it means they might not handle challenges well. I’m looking for someone calm and thoughtful, not just generous or flashy.” Suddenly, her odd question didn’t feel like a red flag—it felt like a test of character.

We ended up ordering simple pasta dishes and talked for hours about our dreams, our families, and the kind of lives we hoped to build. By the end of the night, I realized how genuine and kind she was. What started as a stressful dinner had turned into one of the most meaningful conversations of my life. Walking her to her car, I couldn’t stop smiling. That strange question at the start had opened the door to a deeper connection than I’d ever expected.