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Caveat Emptor: Lawyers and Dating (Episode 1: Tim)
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Summary: Caveat Emptor is a new ongoing series about lawyers and the bad dates they go on. Here, we meet a guy named Tim and hear about a terrible date he went on.

Lawyers and dating



Dating can be miserable, and having a J.D. doesn’t make it any easier. This column is the first of a series we’re starting about lawyers and the bad dates they go on.

I met a man I’ll call Tim at his neighborhood bar in Brooklyn. He was sitting next to me and I heard him talking about contracts and other lawyer-y stuff, so I decided to approach him.

“Excuse me,” I asked, awkwardly. “Are you a lawyer?”

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“Yes,” he said.

“Can I ask you a few questions?”

“About what?” he said.

“Your dating life.”

He thought for a moment, and took a sip of his wine.

“Will you use my name?”

“No,” I said, and he agreed to talk to me.

“So,” I asked. “Are you single?”

He said he was, so I began to ask him about his dating life. He answered all of my softball questions sportingly, and then I popped the one I really wanted to ask.

“Have you been on any really bad dates lately?”

Tim blinked a few times, and then a huge smile crossed his face.

“Well,” he said. “One really good one.”

Tim and his date had met on OKCupid. She was cute, he said, with long dark hair and glasses. When they met up, at a bar, Tim recognized her immediately.

“She actually looked like her pictures,” Tim said. “Which was a surprise.”

When they started talking, things were going well. She seemed smart. They had easy, natural chemistry. They finished their drinks, and Tim bought another round. And then another. It seemed pleasant and fun.

“And then,” Tim said. “She started talking about her ex.”

And not in the low-key, maybe slightly less inappropriate way, like, “Oh, my last ex was a lawyer, too,” or something like that. No, she brought up that she had thought he was “The One.”

Yes, it was weird, Tim said. Very, very weird.

But it didn’t end there. For the next half hour, she kept talking about how great this guy was.

“I think, if we met again, we could probably make it work,” she said. “I think we both know what we’d do differently. We were just in such different places.”

“Uh huh,” Tim said.

At this point, he was feeling very uncomfortable.

“Hold on,” he said. “I’m going to the bathroom. I’ll be right back.”

He went to the bar instead.

“I need a shot,” he said to the bartender. “Whiskey.”

The bartender obliged. Tim took the shot, quickly, desperately. Refreshed, Tim returned to the table, hoping that the brief break might allow him to change the subject.

But no. She kept talking about her ex.

And then she started crying. At the table, on a date, with Tim, the woman burst into tears.

“I’m sorry,” she said. “I just miss him so much.”

Tim, a decent guy, awkwardly patted her on the back.

“Don’t worry about it,” he said. “I understand.”

“He was just such a good guy,” she continued, through her tears.

“I’m sure,” Tim said, still patting.

They sat in silence for a few minutes. Tim downed his drink.

“Well,” he said. “I should probably go. I have to get up early tomorrow.”

The woman nodded.

“Me too,” she said.

And then:

“Would you walk me home? I only live a few blocks away.”

Walking this woman home was the absolute last thing Tim wanted to do. Like, after cutting his fingernails to the quick and adult circumcision. Maybe at the same time. But, overwhelmed, and trying to be a nice guy, he said ok.

The two of them left the bar. A few steps away, the woman grabbed Tim’s hand to hold it.

“I probably shouldn’t have let her,” he said. “That was probably leading her on. But what was I supposed to do? Snatch my hand away and put it in my pocket?”

I acknowledged that yes, that would have made the rest of the walk even more awkward.

Soon, they got to her apartment building.

“Kiss me,” she said.

“Um,” Tim said. “I’m sorry, I just don’t think so.”

The woman made a face at him, as if she couldn’t believe that he wasn’t absolutely enthralled with her, after the great date they had just had.

“Ok,” she said. “Well, have a good night.”

Tim walked back to his apartment, shaken, but relieved that he was free from this date that had turned horrendously awkward and unpleasant.

“When I got home,” Tim told me, “I poured myself some more whiskey, and then passed out in bed.”

Did she ever contact him, later?

“She actually sent me a text the next day,” Tim said. “I couldn’t believe it. I didn’t respond.”



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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