Worst Date Ever

I wrote this last week for my weekly column Beauty and the Beast http://thecomedypoint.com/category/beauty-and-the-beast/ thought I would share it here.

Worst Date Ever

I’m reluctant to classify any of the horrid dates I’ve had as the worst. I don’t want any of these buffoons to receive a superlative, even if it is has a negative connotation. It still says he was the best at something but for entertainments sake, here is ONE of the worst.

One of the Worst Dates I’ve Ever Had

Written by Kendra Cunningham, Still Single

A few years ago, right around this time of year, let’s say Fall 2007? I had just broke up with a guido pseudo bookie who shaved his entire body, hung his football jerseys on hangers, and lived in a 2 mile radius of his entire family. Why? I met him coming off the demise of a three year relationship with someone who quite literally took joy in being as hairy as possible, didn’t even have a closet in the industrial loft he turned into living quarters by putting up sheetrock walls (construction assistant- yours truly) and, I came to find out, sometimes pee’d in a bottle so he didn’t have to get out of bed in the middle of the night. I’m embarrassed to say, I learned this piece of information and still continued an emotional and sexual relationship with him. Why? The sex was good?  Good sex distorts reality. It’s a fact.

So I end up dating a meathead. It could be worse. We break up. Why? The sex was crap? No, I should say “the sex was crap period” it’s a statement of fact not a question. My friend Tiffany was happy to hear we were through. She didn’t like him because sometimes he wore cologne. We all have our things. She was more than happy to set me up with someone. The story she spun was he was a filmmaker, had a good sense of humor, and was looking to start dating after a long distance entanglement with a crazy lady from the Midwest. Fotoball jersey

She puts us in touch and we agree to meet at some sexy bar in the East Village. I show up, I find him, I sit down, I get a drink and the monologue begins. First he tells my breasts all about how he’s a vegetarian. I’ll be honest, when guys pay a lot of attention to my tits I don’t feel objectified, I get jealous. I do. I get jealous of my own mammary glands because they’re getting all the attention. I feel left out.  So I’m sitting there feeling like my date isn’t paying enough attention to me when I start to realize he’s been talking for a really long time. I interject “so Tiffany tells me you’re a filmmaker” .  This time he looks me in the eye, every couple of seconds and tells me about his experiences with Oliver Stone. It starts to become apparent he is not going to ask any questions about me. I order a hamburger. Take that ya vegan fuckwad.  Apparently his crazy ex girlfriend loves hamburgers too, go figure. Two people who like hamburgers? What are the odds? 

He starts in on his ex and how she only wanted him for his money. I start to suspect he has been drinking all day. So now I know he knows Oliver Stone ( braggart), he’s a vegan or vegetarian or some sort of limited menu choice eater ( yawn) and he fancies himself a rich man (whoopee ding dong).  I offered him the last bite of my burger, just to be an asshole. It crossed my mind to say “ you know I came here tonight hoping for a one night stand but your personality cock blocked you. Feel free to monologue that to Oliver Stone while eating your gold dusted edamame, you self engrossed poser”  but we have mutual friends . That’s the thing about getting involved with somebody who has mutual friends, you gotta play nice. It sucks!  He asked me if I wanted to go back to his place and smoke pot.  I told him I shouldn’t . I left him on the corner with a “I get really horny when I’m stoned” .

He texted me a few days later and asked me to go to some event.

I wrote back “Too tired, spent the night with an NYU linebacker and a bong. Gotta get some sleep.”

Dating sucks.


Man looking at boobs



Kendra is a stand up comic living in Brooklyn where she owns a super comfortable bed. She spends most of her time wondering where the hell her sugar daddy is and hoping he didn’t settle.



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