It could have been worse: The Guaranteed Miss

December 9, 2009 at 7:00 am | Posted in Dating Stories | 1 Comment
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Single City Guy is a dating blogger who lives in New York City (Brooklyn to be exact.) He shares his dating stories, experiences, advice and the male prospective of dating thru his blog at Single City Guy will frequently post his dating stories (the good, the bad and the ugly) on the Thread Blog. This story was originally posted here.


There’s a general rule to dating: if a person looks at you more than twice, they’re interested. For a period of time, my dating failures made me timid when approaching women at bars or clubs. Even if they were giving me clear signs they were interested. I began to think of approaching women as predestined failed attempts instead of potential dates. One night, while out with friends, my reluctance ran into someone who was very interested. Let’s call her Hot and Direct.

Hot and Direct kept glancing at me throughout the evening, she was with her group of friends, I was with mine. She made it clear she was interested. My friends noticed her interest and began to goad me in approaching her. I was paralyzed with fear. Quickly, my friends began to add some peer-pressure and gave me an ultimatum, either I introduce myself or they would do it for me. This situation was turning into a bad episode of 90210. With enough peer-pressure and liquid courage, I approached Hot and Direct, breaking every “pickup” rule I’ve learned. I introduced myself, name first, and began to stumble while talking to her. The fact that she was interested, even with my stumbling, was a good sign. I’m sure for many guys, this would be a guaranteed success. There wouldn’t be any possible way I could mess this up. This was one of those nights I would find new ways to turn opportunities into missed opportunities.

The first mistake I made was answering her questions with questions. When asked how old I was, I responded with “Well how old do you think I am?” I was trying to be playful, mysterious. I quickly found out this girl wasn’t in the mood to play those games, especially ones I’ve finished reading from a certain book. I was able to redeem myself, first by apologizing and second by buying her a drink. This bought time to prove myself. The next few moments went extremely well, she was very direct with some of her questions: Was I straight? Was I single? If I’m “big”? I can handle woman whose very direct, if anything I prefer it. It felt comfortable answering each question honestly and directly without worrying about not being myself. I was comfortable.

I’m a very honest person and tend to be very blunt and direct. The rapid-fire questions Hot and Direct was shooting at me were  easily answered and placed her more at ease. The situation was beginning to turn into my favor. Hot and Direct pointed another woman in the room and said “She’s really beautiful! What do you think?” The woman was very attractive and I answered, “She’s really cute!”

Have you ever seen the expression of a golfer when he misses a putt two feet away from the hole? The expression of a wide receiver who drops a football when he’s wide open? A basketball player who misses a dunk? That expression was plastered all over my face. One of the most important rules about courtship is to not acknowledge other girls. When asked about another girl in the room, IGNORE them. This is a trap! One I had fallen into.

Needless to say it went downhill from there. I tried to recover what ever momentum I had lost, but it wasn’t going to happen. The only things Hot and Direct that night would be the “movies” I would be watching later.

(Image Credit: OGA from Flickr)


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  1. lame

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