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Self | Dating
Mismanaging Expectations and the Slog of Online Dating
Why you should proactively guard against cynicism.
Jen walked through the dimly lit restaurant doors and I was pleasantly surprised. Her beautiful white smile, long auburn hair and pretty eyes far surpassed her pictures. She walked over and said, “Sean?” I stood up and we had an introductory hug. Then our date rolled down a cold and muddy hill of incompatibility.
She was negative and complained about everything and made insulting jokes at my expense. She drank like a fish — which wasn’t a red flag on its own, but it struck me as odd, given she was an addiction counselor. As she talked, I had a vision of her in a counselor’s chair with a margarita, lecturing her patients on the benefits of sobriety.
Rock bottom was when she said, “I know this might sound off but I need to text my -ex really fast.” She added that she wasn’t hung up on him but needed to tell him something because she’d just moved out a week prior. It was an earful. I sat and wondered how many things could go wrong on one date. “Maybe the waiter will spill a drink on me next,” I thought.
She was still flirty and made a few funny jokes, so I agreed to go out on a second date in the spirit of giving things a fair shake. I’d only been…
