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Dates Gone Wrong: That Time My Date Got Arrested

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This happened 9 years ago, when I was 21. My date — whom we will call Zack — was about my age, a business owner, and very charming. I had met him at work — we were both Orthodox, and I was excited when he suggested that we should go out for dinner in Manhattan.

Our date progressed uneventfully up until the waiter brought the check to our table. One by one, the plastic came out. Swipe, declined. Swipe, declined. Swipe, declined. Zack wasn’t doing very well. I was horrified and embarrassed for the two of us.

He finally paid in cash and we left in a hurry.

Back in the car, perhaps to take my mind away from his questionable financial standing, Zack suggested that we take a drive before heading back to Brooklyn. He asked me for my favorite part of town. Having only recently moved to New York a few months prior, I told him Times Square was still very exciting to me. “Times Square, it is!”

As we approached Times Square, I craned my neck to gaze at the flashy advertising sprawled across the various skyscrapers. Being an advertising junkie, this was heaven.

All of the sudden, flashing blue and red lights filled the car and sirens blared. “Pull over!” a loud voice yelled.

“What had we done wrong?” I wondered. We weren’t speeding. Were we driving too slowly?

“It’s just a random check,” Zack said. But he didn’t look convinced. I saw that three other cars were being pulled over as well.

We rolled to a stop at the nearest curb. A female cop approached the driver’s window as it steadily rolled down. “License and registration,” the cop demanded.

Zack leaned over me to grab the registration documents from the glove compartment. Then he fumbled around in his back pockets until he found what looked like a very ragged driver’s license.

The cop took the papers back to her car and sat. And sat. We waited in silence. The minutes crawled by. What was going on, I wondered?

It sure didn’t feel like a random check with this guy. As the minutes passed I became more and more anxious. Finally, I saw from the rearview mirror that the cop was heading back toward us, except that she was flanked on either side by male officers as well!

I started panicking. Why would they need three cops for a random check on one vehicle?

“Is there anything that might be wrong?” I asked. “Maybe,” Zack stammered. “My license might be suspended. This car is registered upstate, so any tickets would go to that address. It’s possible that there are tickets outstanding, which could mean that my license is suspended.”

It didn’t take long to find out.

“Sir, please step out of the vehicle with your hands where we can see them,” the cop barked.

With his hands outstretched in front of his body, Zack clambered out of the car. I couldn’t bear to look. How embarassed he must be, I thought. Just when he thought things were going smoothly, he gets arrested in front of his date?

That’s right. They handcuffed him. Right in front of me.

The metal clicked shut tightly around his wrists. “Why are you arresting me?” he asked them. “Because it is after 11 p.m. and the judge cannot hear your case until tomorrow morning.”

I was shellshocked. I couldn’t move.

“Take my phone from under my seat and call Sam*,” he said, his voice steady but hurried. I nodded. The driver’s door shut and I found myself alone in a vehicle that did not belong to me, in a city I did not know well, with no clue how to get back to Brooklyn.

About 40 minutes later I knocked on Zack’s apartment door. His roommate answered, I handed him the keys, and turned to go.

Never again, I swore.

Background checks from now on.

Names have been changed to protect anonymity.

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