At first I just laughed at Leonard, aka OKCupid user “Iwntmyjewwifenow.”

And then I realized I couldn’t stop thinking about him. I mean…he was just so weird. His erratic capitalization and use of punctuation suggested someone who was at least a little nutso. So I decided I had to meet him. It would make a fantastic blog post.

I had previously messaged him to tell him I would never be interested (because I’m an asshole who gets off on being rude to people on OKCupid).

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But I ate my words and sent him the following message:

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I knew it would resonate. It was just the kind of creepy sappy language that he used all over his profile to try to catch his “Jewish best friend on fire for life.” And I was correct. He responded.

First he immediately sent me his phone number because he couldn’t “access OKCupid from [his] home computer.” I did not call, but I told him he could text me. But no. That wouldn’t work for Leonard.

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Who doesn’t own a cell phone? Like, even a flip phone or something?

Anyway, apparently Leonard doesn’t. So we kept messaging back and forth instead. He told me his ex quit smoking for him, and he hoped I would, too. He reminded me that he had no job. Informed me that he lived with his parents on the Upper West Side. He asked me if one day “when we both have money (very soon for us both I hope)” I would move to the suburbs with him. I ignored it. It was weird, but I had had some idea of what I was getting into when I messaged this guy.

My profile says I’m a writer. He asked me what I wrote. I told him I was working on a book – his response?

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Oh, of course. A book on tickling etc. Who hasn’t written one of those?

And then this, out of the blue:

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He started and single-handedly sustained a very long conversation about where our parents were born, where our grandparents were born, what our parents did, what our grandparents had done. It was, obviously, stimulating, but I decided to change the subject.

“Now, not to be rude,” I asked, “but how do you expect to have a family if you have no job and live with your parents?”

He ignored it at first, so I asked again. And then this was his response.


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Oh, of course, you’ll move in with me!

And is the “short” comment supposed to be an insult? I mean, I’m cool with being tiny. I like it about myself. But…what the fuck?

At this point, I was beginning to doubt that I could follow through with actually meeting this man. I can handle a lot, especially for the sake of the blog, but I was starting to think that Leonard would probably tie me up in a basement somewhere and talk to me about how his grandfather started the Port Authority. And then these lovely messages cemented things for me.

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YES. “I believe I will love you” and “I don’t want to wait forever to be a dad, but we don’t have to make it happen on the 1st date either.” In the span of about a minute, Leonard had already declared his inevitable love for me and told me that he couldn’t wait to knock me up with a little Jewish baby on fire for life.

And that was too much, even for me.

At that point, I knew this could only end with me tied up in a basement. I sent another message saying that everything was getting too creepy and I couldn’t do it. He sent a few more begging me to reconsider and telling me that “yes I want to be a dad like yesterday” but that he’s much better on the phone, so we should talk. I refused.

So, Leonard didn’t get his Jewish best friend on fire for life. I didn’t get to write about what would definitely have been the weirdest date I’d ever been on. But I still think I made the right choice – even though it was tough.