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Caveat Emptor: Lawyers and Dating (Episode 2: Ella)
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Lawyers and Dating


Summary: Caveat Emptor is a dating column about lawyers on bad dates. Here, we talk to Ella about hers.

Click Here to Read About Another Lawyer Date Gone Horribly Wrong


A lawyer friend, Ella, reached out to me about a terrible date she had been on – with a fellow lawyer.

Although the two didn’t work in the same firm, they had met at a work event.

“He was cute,” she said. “Like, exactly my type. Tall, skinny, with glasses. And totally charming.”

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They met up at a bar in Midtown Manhattan, after work. He bought her a drink, and they sat down at a table. It started with small talk – what TV shows they watched in their down time, what music they liked. And then it turned unfortunate.

“Where did you go to law school?” he asked.

She responded, and then, immediately, he started talking about himself.

“I went to Georgetown,” he said. “I got straight A’s.”

“That’s great,” she said.

“Wait a second,” she said to me, getting out of the story. “I need to mention that he was thirty-five. He hadn’t been in law school for at least ten years.”

Yes. He was bragging about how smart he was in law school. When he was twenty-two.

Anyway, back to talking about himself.

“I thought I wanted to do criminal law,” he said. “Like, a DA, or something. But then I got this great job at a law firm.”

“Mmhmm,” Ella said. “I’m gonna get another drink.”

She got up from their table and went to the bar. She ordered a gin and tonic and went back to her date.

“So anyway,” he said. “I got this job at a law firm. And they pay really well.”

“Mmhmm.” Ella took another sip of her drink.

“Like, really well.”


He proceeded to tell her how much money he made. And how much his apartment cost a month. And the trendy neighborhood he lived in.

“I live in Brooklyn,” Ella told me. “There is no way I have anything in common with someone who lives in the Meatpacking District.”

For the rest of the date, he talked about how impressive he was. Soon, Ella stopped even trying to engage, and just resorted to responding with, “Oh, nice,” and, “Cool.”

“Want to go somewhere else?” he asked.

Ella wasn’t ready to go home yet, so she accepted.

“I figured I’d get some free drinks,” she said to me.

He took her to a swanky lounge with $17 cocktails. The hostess told them that there was a private party going on, and they couldn’t come in until seven. And then he threw a fit.

“Do you know who I am?” he exploded.

The hostess stayed calm.

“I’m so sorry sir,” she said. “I wish I could help you out.”

“I could get you fired!” he yelled, and then grabbed Ella’s hand. “Come on. We’re going.”

Ella was mortified. She turned back to the hostess and mouthed, “I’m sorry.” When they got outside, Ella told him that she had to go home and feed her cat.

“I had a great time,” her date said.

“That’s nice,” Ella said, and then got on the subway back to Brooklyn.


If you have a bad date story to contribute, please get in touch with the author at – I’d love to hear it, and let you appear here! No real names.



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