Our Terrible, Horrible, No Good, Very Bad First Date

Neither Jason nor I am a fan of Woody Allen, so to choose one of his movies to see on our initial date was our first mistake. We only went because everyone was saying how good it was. When we got to the theater, the line was long and the theater was packed. The only two seats we could find together were in the front row. We sat with our necks crooked up for all 107 miserable minutes of the film. By the time it finished, I had a raging headache and I never wanted to hear the name Woody Allen again.

We’d saved eating dinner at the Green Door Tavern for after the movie. Throughout the show and walking over to the Tavern, I worried about having enough cash to pay for dinner. Since I’d asked Jason out, I figured I should pay for it. But I’d run out of time and hadn’t made it to an ATM to get more. I didn’t know if the Tavern would take my one credit card. Besides being distracted by how much money I didn’t have in my purse, it was the coldest night Chicago had suffered in years. It was freeze-your-nose-closed frigid. It didn’t help that I’d lost a contact the day before and had to wear my glasses. Not only did they nearly freeze to my face, but every time we went inside, they fogged up. Jason was having contact troubles of his own, so he had on his glasses too. So when we walked into the Green Door Tavern, a dimly lit restaurant with a bar at the front and dinner seating in the back, both of our spectacles immediately clouded up and were useless. We both took them off, because you just don’t keep your glasses on when they’re steamed up. But when you’re as blind as the Three Mice, and the maître d’ says, “Follow me,” and takes off into the dark restaurant to lead you to your table, there is really nothing you can do but stand there by the bar totally lost waiting for your glasses to warm up so you can get your vision back. In the meantime, losing your sense of sight, and having the maître d’ come back and snap, “Are you coming?” just makes everything a little more on edge. Especially when your headache is only getting worse after the twenty-below wind chill just blew the snot out of your face. (Sadly, literally.) Pressed by the host to get a move on, we stumbled our way back through the dark while trying to wipe clear our lenses. We finally floundered our way to the table and awkwardly got our eyesight straightened out so we could pay attention to each other again.

I ordered something that didn’t cost too much, the whole time calculating how the total price of our order corresponded to the cash in my purse. It was the first time we shared a meal without eight other people around. And I found out that Jason was an introvert, a very quiet man. And that I was uncomfortable with silence and babbled stupidly to fill the silence. Then some guy, out of nowhere, came and sat down at our table. At first I thought Jason must have known him. But then it became clear he didn’t. Afterwards we wondered aloud if he was the manager checking to see if we liked our service and food but just forgot to explain himself. In Chicago, you never really know who the strangers are around you. At least he didn’t pick the French fries off our plates. And he did help fill a few minutes of silence for us.

When dinner was over, Jason picked up the check and saved me the embarrassment of counting out my quarters. We returned to my building, walking through the horrid wicked cold again. When we went through the revolving door to my lobby, of course both of our glasses fogged right back up. Being clever, I said, “Bye again,” and by the time I got my stupid glasses cleared and back on, I was standing there alone with my doorman. Jason had heard me tell him Bye so abruptly, he took that to mean something like “Go away” and he just kept going around that revolving door back out to the brutal Chicago night.

Though I didn’t know yet why he just left, I did have my headache, and with the whole awkward glasses thing making normal function impossible, and that extra guy at our table, and the stress of no money, and the horrible movie, I didn’t go running after him. So a bit flummoxed, I took the elevator to my 11th floor apartment. On the way up I realized that I didn’t have my keys. They were in my purse. And my purse was not on my shoulder! Somewhere in the course of the night, I’d lost it. My doorman let me use his phonebook and phone, and I called the Green Door Tavern, where I thought I had it last. They indeed found it beneath our table. (If only I’d paid the bill!) I couldn’t walk back by myself — the restaurant was right by Cabrini Green. So I had my doorman switch on the taxi light for me outside the building’s front door and I caught a cab back.

My purse was safely returned, and with my meager cash inside, I paid the cab fare to go get the stupid thing. When I got home, I thought, “Oh Well.” Once in a while you had those kinds of dates and you moved on. No need to sweat it. I’d just have to get through the remaining meal our dinner group had scheduled and I wouldn’t need to see Jason again. We could put it behind us and chalk it up to dating and how not all of them worked out.

At our next dinner group, I was standing with the rest of the gang outside the restaurant waiting for late comers, of which Jason was one. I was thinking about how I’d just play it cool and not worry about the embarrassment of an awkward evening.

But then he walked up and smiled. And I realized that my heart had taken off without me. We were going to have a second date, I was certain.


— Hello! I have quadruplets, I’m an editor and writer, and I like to make every subject as interesting or funny or thought provoking as possible. If you’d like to follow me, I’d love the connection with other readers. I blog every day, on a year-long dare. Each day is a different theme, with parenting and kids and writing and history and flash fiction and op eds. I’d love your support! Thanks!

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