The Guy Who Cried On Our First Date (Yep, It Happened)

Once upon an OkCupid message, a dude named Andrew messaged me.

His message was charming and thoughtful, unlike the many (sarcasm intended) ‘Yo baby, wasssssup’ spams I get and frankly never understand because, does anyone respond to that?! Anyway, we did the flirty back and forth text tango for a day or so before he asked for my number. I made him give me a pickup line for it, he went with the cheesiest one, and I smiled at my desk at work when I read it.

Two days later, we were finally setting up our first date when he suggested a well-known, old school Italian joint in the West Village. I had always wanted to go but could never afford it, and it felt really odd accepting such a generous offer from someone I hadn’t technically met. But he was tall and had a great, interesting job and we seemed to like the same things, so I gave in and made an off-hand comment insisting I’d buy him drinks after dinner.

I wore a red dress I got at a sample sale with some pretty tall heels (he said he was 6’4″!), and I arrived just a few minutes late, finding him sipping on a dirty gin martini at the bar. I was instantly intrigued; it’s my favorite drink.

This was originally posted on To read the rest, click here.


One thought on “The Guy Who Cried On Our First Date (Yep, It Happened)

  1. Pingback: Why I Haven’t Given Up On Love |

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