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Happening The Post

Awkward Dates at Postino

February 12, 2024

Grainy photo of a man and woman at a restaurant table

We acknowledge that our four walls are the backdrop to many encounters such as beautiful love stories, but what’s the fun in that? We asked our guests to submit their best, most awkward dates as Postino. And remember, we’re laughing with you, not at you!


“One time I was with a guy and we were talking and had just ordered our board (so pretty early on in the date) and he legit said to me ‘do we have to fill every second in conversation? Can’t we just sit here and enjoy?’ So we literally sat in complete silence the entire rest of the date.

The worst part is the food wasn’t even there yet. Needless to say I enjoyed the rest of our bottle and stuffed my face with bruschetta.”


“As we arrived, there was a bit of a wait time for a table so the host kindly asked us if we’d like a glass of wine while we waited for our table. We said sure why not and as we were pulling out our IDs, my date had whipped out his wallet and a condom flew out and landed on the ground right in front of everyone. He immediately stomped it with his foot and slowly slid it back towards him to put it back in his pocket.”


“I was unimpressed with his outfit and his awkward mannerisms and so I told him, in order to get the date over quickly, “I date to marry, just so you know.” Instead of scaring him off, he said he agreed and that led it to more awkward convos. To make it even more awkward, we ordered a bruschetta board but we each only ate one bite. Regardless, my now fiancé.”


“We had a great conversation that came to an abrupt end when he noticed someone on the other side of the bar. He put down $10 and left – barely saying goodbye. The bartender looked at me and said… his wife just walked in.”

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