When Dating Goes Wrong: Expectations vs. Reality

Dating in a small town is like shopping in a boutique—you’ve seen the inventory before, but every once in a while, you convince yourself to take another look. Enter him. A local business owner, real estate investor, and, as of last November, a persistent suitor. After months of polite deflections, I finally said yes to lunch.

He arrived before me—points for punctuality. I walked in, gave him a warm but hug-free greeting (a decision I’d later regret), and took my seat. The conversation? Think weather updates and local road conditions. He was shorter than me, which I honestly wouldn’t have minded if he exuded a strong, confident presence. Instead, his hands trembled so much I thought he might be reenacting an earthquake drill.

Trying to put him at ease, I leaned into my best soothing therapist voice. “So tell me about your latest project.” But instead of steadying himself, he steadied his drink. And then another. And another. Meanwhile, when the food arrived, he picked at his plate like a bird on a diet.

At the end of lunch, we split the bill—a detail I didn’t mind but also didn’t swoon over. He walked me to my car, where I did finally give him a hug, a small token of goodwill for his valiant effort. I figured that was the end of our romantic misadventure.

Until the text came.

“We should conduct some kissing.”

Conduct. Some. Kissing.

Not share a kiss. Not I’d love to kiss you. But conduct some kissing—as if this were a science experiment or a contractual obligation.

And just like that, it was clear.

  1. We had zero kissing chemistry.
  2. That date was a one-and-done experience.
  3. I desire someone intellectually stimulating, masculine, and sexy—not a nervous wreck drowning in cocktails and formulating romance like a board meeting agenda.

Bless his heart, though. Maybe his next date will be less of a high-pressure boardroom presentation and more of a relaxed, mutual connection. As for me? I’ll be over here, patiently waiting for a man who doesn’t need liquid courage to keep up.

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