Dating Disaster: He Said I Looked Like…


dating disaster
A date takes an awkward turn after an unexpected family resemblance.

Everyone—god love ya if you haven't—has a tale of dating gone wrong. Whether it happens on a blind date or three months into a blooming relationship, these disasters usually strike out of the blue and leave you stunned, slack-jawed and, often, downright offended. And that's exactly why they make for such good stories. Hopefully, too, they teach us a thing or two about the pursuit of love. Here's my tale.

I had known Billy* for five years through mutual friends, and at some point we started hanging out independently. I was still sailing on the friend boat when Billy indicated his winds were now blowing from a different direction. I wasn't interested in him romantically then, but we did seem to get on quite well. And so ensued several months of friendly, flirty hangouts, during which I grew more and more fond of the fellow. From Friends To Lovers


We spent one Friday night playing pool with friends, drinking beer and chatting on the front steps of a house party. We talked about the benefits of therapy and shared our respective "here's what made me need therapy" stories (dutiful New Yorkers that we are). And then we kissed. We went to his apartment to walk his dog and, inevitably, kissed again. It was exciting, after the months of build-up. That is, until he suddenly pulled away and said, "I can't do this."

I thought he might be joking. "Um, what?" I asked. "Why not?"

"Well," he responded, without so much as a stifled smile, "you look exactly like my aunt."

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