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FFJD: A Date with Jon Stewart.
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FFJD: A Date with Jon Stewart.

by
November 1, 2010

I was innocuously poking around on JDate when I got an IM from the user TRUTHY4U. At first I thought it was a joke – he was very clearly, at47, far and beyond out of my age range. I thought that maybe I’d make an exception, given that I am trying to broaden my whorizons and not leave any stone unturned.

I was dubious at the prospect of this JDater, when he revealed his name to be Jon Leibowitz (Stewart is apparently what he goes by), I thought maybe I should give him a chance. If nothing else, maybe I’d get a good story out of it. Although he lives in NYC, he told me he was going to be in DC for the weekend and would really like “to get to know me.” Yeah, me and 215,000 other people, although he claimed I was different.

I told my friends to make sure they had heard from me after we had our drinks and that I wasn’t in little bits at a random Comedy Central studio space.

Where we went: Hudson. I love the atmospherics of this place, chic. Good matzo ball soup, of course.

What I wore: I didn’t want him to think I was too suggestive at 24 years his minor, so I decided on a pair of JBrand skinny jeans, a cute silk Tucker blouse, and Steve Madden wedges. I wanted to scream intellectual and maybe available if you’re a young 47, so I was sure to wear my glasses instead of my contacts. His profile said he was 5’10 but I was dubious.

He was nice, but he kept asking me to say and do all of these weird things. I guess he sort of had a thing for girls saying “I am not a witch. I am you.” But to each his own.

I actually really liked Jon, and he was cuter than his JDate pictures, (which were all annoying, professional and geeky head-shots) but he was still really old. He knew a lot about current events and politics, which I liked, but he kept making fun of me with obnoxious video montages.

In the middle of the date, Kareem Abdul-Jabbar showed up. Which I thought was strange, but Kardashians date athletes, so I just figured it was another stepping stone in my career, managed by Kris Jenner.

He was sweet and gentlemanly, but I spent most of the evening thinking about another guy I had gone out with recently, Steve. In typical FFJD fashion, we were sitting at the bar and he is with a bunch of people I know at a table nearby. I’m mortified. I know it’s him because of the little bent right ear.

Shit.

And I think that he and Jon are frenemies, and you don’t want to get in the middle ofthat. I didn’t know what to do, and Jon hadn’t seen him yet. When Jon got up to go to the bathroom, my heart dropped as Steve came over.

“Hey Meredith,” he said, with a little bit of an eyebrow raise. “I know a little bunker we can go to and have some quiet time together. I know you’re out with Jon, but let me tell you, I’m funnier. I think it’s time you let a shiksa goddess show you around.”

I took a few slurps of my matzo ball soup, and did what all terrible JDates do – bolt.

As we ran across the street, hand in hand — I didn’t look back.

Follow FFJD on Twitter and submit your Halloween or other shameful/awesome date story to fiftyfirstjdates@gmail.com.

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Meredith Fineman was born and raised in Washington, DC. She attended the University of Pennsylvania where she majored in Communications, with a minor in Spanish, Jewish Geography, and BBMing. She spent the past year living and working in Buenos Aires, Argentina. She is now back in the Northern Hemisphere and makes fun of her dating misadventures and her self-indulgence on her blog, Fifty First (J)Dates: WWW.TheFFJD.com Justin Bieber says follow her on Twitter @TheFFJD and be a fan on Facebook. He is also her (g)oyfriend.

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