Hot Josh’s Valentine’s Day Payback

Valentine’s Day. A day for romance, overpriced chocolates, and people pretending to be more in love than they actually are. I had a date lined up with someone I had been seeing casually—nothing serious, but I figured dinner at a fancy restaurant wouldn’t hurt. Plus, I fully expected not to pay for it.

Now, before anyone gets judgmental, let’s be clear: I had my reasons. The last few times I had gone out with this particular date, I had picked up the tab. Every. Single. Time. This was supposed to be her turn. Fair is fair, right?

So, we arrive at this upscale place—the kind where they serve food on giant plates with little specks of sauce that look like modern art. The waiter hands us menus, and I make sure to mention how much I’ve “been looking forward to a nice treat.” She smiles. I assume she gets the hint.

I order the steak. Not the cheap one, either. She orders a salad—concerning, since I’m expecting a full-course meal from her side to balance this transaction. But maybe she’s just one of those people who eat light on dates.

The night goes well. We talk, we laugh, we pretend to care about the love stories of the other couples around us. Then, the check arrives. And she doesn’t even flinch. She just sips her wine, waiting.

I clear my throat. She smiles. I smile back. A full minute passes.

Finally, I break. “So… should we split this?”

She tilts her head, genuinely confused. “Oh, I thought since you picked the place, you had it covered.”

Picked the place? I had suggested it. That’s not the same thing!

Realizing I had been outmaneuvered, I swallowed my pride (and my dignity) and pulled out my card. The waiter gave me that “Ah, another one who thought he had it all figured out” look.

Lesson learned: Never assume someone else is going to pick up the tab, even if it’s “their turn.” Also, maybe don’t expect a payback meal on Valentine’s Day—it turns out, love doesn’t operate on a ledger.

But don’t worry—I made sure to take full advantage of the chocolate-covered strawberries before leaving.