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It was one of my favorite events of the year: the Brazil Carnaval at 4th&B. She and I had just met, but we danced the samba as if we had known each other forever. The loud, pulsating South American beats accompanied by the six Jack and Cokes I had consumed gave me a semblance of rhythm that I didn’t know I possessed. We danced, I spun, she dipped, we kissed. She said she wanted to get to know me better; I’m sure I said the same. I gave her my business card, which has my cell number on it, and told her to call. (In my stupor I didn’t think to get her number.) I left feeling like the biggest pimp of all time.

I woke up feeling like the biggest loser of all time. My friend Jack Daniel’s had turned on me. Last night’s memories were a jumble. I remember the drinking, the dancing, the music, the kiss. What I couldn’t remember, thanks to the alcoholic haze, was what she looked like. I assumed she was pretty, but Mr. Daniel’s had been successful in the past in causing me to slum it. Alas, I didn’t get her number, so I resigned myself to the fact that I would never know — until she called me three days later.

I was giddy and apprehensive at the same time. Our chemistry from Carnaval carried over to the phone conversation, and we set a date for the following Friday. Now, from my limited experience with the fairer sex, the pretty girls don’t chase. It’s up to the guy to initiate, and if you don’t have the number you’re out of luck. Her calling me should have been a warning, but my ego was shouting, “Of course she’s cute! You’re good looking, you’re awesome. Any hot girl would call you. She’s going to be pretty — go out there and get it!”

Despite my ego, I was still skeptical, so I decided to set the date in an area that I knew I wasn’t likely to run into anyone I know. I chose Chula Vista. I arrived early at an authentic Italian restaurant by the name of the Olive Garden to secure a table. The hostess told me that it would a be a 40-minute wait, which shows you that the Chulajuana residents know good eating. I sat outside and waited for her to arrive. I suspected that she must be doing the classic hot-girl move of being late on purpose. She finally showed, wearing heels, black capris, and a white top. She smiled, I smiled back, we hugged, and I hated myself. Yes, my friends, she was ugly.

It was at that time that I wished I was an even bigger jerk than I am so that I could have made some excuse and gotten out of there. But I stayed. She didn’t make it easy, though. In addition to being offensive to my eyes, she was doused in some terrible perfume, stinging my nostrils with every whiff. She was a talker, too. Everything from her work to her hobbies to her family to the time she was proposed to. Knowing that at least at some point someone liked her enough to want to marry her made me feel better about the fact that I was sitting there with her. Aside from that tidbit, I was bored.

Every time the waiter came by our table, he would smirk at me in a “Dude, are you serious?” kind of way. Plus, our order was forgotten by the cooks, which lengthened the date by 30 minutes.

I paid for dinner and walked her to her car. We exchanged goodnights, and she drove away. I shook my head, cursed life, and vowed never to let Jack Daniel’s get one over on me again.

Tell us the story of your breakup and/or date from hell and we will publish it and pay you ($100 for 500-2000 words).

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lallaw June 7, 2008 @ 3:39 a.m.

How do you know she didn't think you were "fugly" and was just trying to be nice? I thought your story was classless. You're the kind of guy us "pretty girls" won't go out with. Typical. There's a good reason why you're still single chum.


magicsfive Nov. 11, 2008 @ 8:16 p.m.

Why was it classless? Because he was being honest? I totally disagree. This story was one of the best i've read..........he went out with her, was kind to her, and no harm done, sounds like.


iamjello2 Jan. 12, 2009 @ 12:27 p.m.

You can tell he's classless because he went out for a first date at Olive Garden!


magicsfive April 9, 2009 @ 6:59 p.m.

lol well yeah i will give you that much...eww. i can't stand olive garden. but i do think he handled it well. i mean he could have ditched her, or been rude to her. sounds like she had a good time... xo


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