When I was stuck in the Jewish dating world, and thank God I wasn’t stuck there for too long, I very quickly lost most of my sanity. It was a rapid process of grey matter deterioration where I felt like I was being pithed like a frog. One day I decided I wasn’t going to take it seriously anymore, so I radically changed my approach. Instead of trying to keep a conversation going or looking at the girl with images flashing in my head of what kind of Shabbat Candlesticks we’d have in our home when we were married or what kind of Bar Mitzvah gifts we’d give to our future son thirteen years from now (granted, I never intentionally thought about these things, they just infiltrated my mind) I was going to take control and do whatever I wanted. This meant I wasn’t going to plan anything, and I was going to be fully myself.

I’m a very random person, so I decided I’d do something completely random. I met the girl at Columbus Circle at 59th street in Manhattan. She asked what we were going to do. I told her I had everything planned out to a tee and we’d be doing the first thing that randomly came to my head. I saw a Wholefoods right across from me and decided we were going to go there and buy three strange pieces of fruit and then hand them out to homeless people on our way out. Why the heck not?

She was not happy about this. It was too adventurous. But I didn’t care, because I wasn’t going to do what I wanted, not what she wanted. Of course I was continually trying to get her into the whole idea of doing something weird, but she had none of it. Encouraging her to pick out a weird fruit, trying to get her spirits up, but it wasn’t working. We ended up getting a star fruit, an “ugli grapefruit” which looked something like a large green warty Sukkot Etrog, and a cactus leaf I guess you were supposed to use for cooking or something. What homeless person would appreciate a cactus leaf I hadn’t quite thought of at the time.

I could feel her stress level increase exponentially every time I picked out something, and when I got the cactus leaf, she was on the verge of hitting me. But even worse, when we went to the checkout counter, the sticker on the cactus leaf was missing and the cashier had to call the manager to find out the price. It ended up being something like 89 cents but in the meantime the cashier was eyeing us strangely and saying, “What the heck is this thing? Did you get it here?” The girl’s face started turning white.

The whole time I was cracking up inside.

We held up the line for about 5 minutes, and finally got out of the supermarket. We went upstairs, the girl visibly shaken. There was an art exhibit upstairs, so I asked her this question. “If you could take home something in this exhibit, what would it be?”

It was a lame question. If I could do it over, I’d tell her to teach me something about the exhibit. She was an art major, and having girls teach you things about what they know is always very good and attractive. But anyway, she said this: “The Audrey Hepburn picture.”

“Who is Audrey Hepburn?”

“She’s an actress,” she answered.

“Anything else you want to tell me, feel free.”

“I want to go home now.”

She had had enough and just up and left, but  I felt liberated. I did what I wanted and she didn’t like it. I went to the bookstore and decided to talk to random women for practice. It was the best worst date of my life.