An Embarrassing Mistake That Led Me to My First New Year's Resolution

I tried not to make any New Year's resolutions this year, but the fact of the matter is that New Year's resolutions help me get over the end of the holidays and the frigid Winter weather in New York City.

So, I'm going to share my seven New Year's Dating Resolutions with you in the next post. But first, I will share the embarrassing story that got me thinking and led me to make my first resolution: Don't assume I'm destined for bad luck, and that fate has a conspiracy against me:

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My checkered past in the dating world is marred by a venomous concoction of bad luck and stupid mistakes. It's hard to pin the moment when I first realized that things never line up right for me. But, one mistake does sum it all up...

In second grade, I had my first crush on this amazing blonde bombshell named Caroline. I worked for years to get comfortable talking to her, but just as I had gotten to a great point with her, she transferred to another area school.

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Unfortunately, this is not the end of the story. Fast forward to my sophomore year in high school. One night, my friends and I were looking for something to do (equation: four high school boys with a car and nothing to do = trouble). We decided to head over to a local convenience store to see if we could buy a porn magazine.

Of course, I was nominated by the other three to do the dirty deed. They stayed in the car while I had to try to accomplish the feat that only 18-year olds could do.

When I got inside, I clammed up: no way the cashier would believe I was 18. So, I decided to ask someone who came in to buy the magazine for me. A girl came in that looked like she might attend a nearby college. I figured she was the right combination of young enough not to freak out by my request, but old enough to get away with it.

I approached her:

"Can you do me a huge favor?"

"What do you need," she asked.

"Um...can you buy me a porn mag," and I gestured at the porn section on the magazine rack that was covered in plastic jackets and seemed roped off like a VIP club. The worst part of it all is that I said "porn mag". This phrase made me sound like an expert, or an addict to porn. "Mag" was especially shady.

She backed away. "Oh my god," she said.

Humiliated, I bought a pack of gum so I could look like I had some kind of purpose, and I attempted to get back to my car.

Before I could make it, I heard a voice from a car in the parking lot: "Rich, is that you? Rich Santos?"

There, in the passenger seat of the car, was Caroline-sparkling more than ever. We started to have a conversation and it was better than ever. If I couldn't return to my car in triumph with a porno magazine, I would return to the vultures with a date with super-hot Caroline. Just as I was about to go for it, the driver (who I had not noticed because of Caroline's sublime glow) spoke up:

"Oh my god, you're the guy who asked me to buy the porno magazine!"

The girl I had asked to buy the "mag" was Caroline's friend! It was over.

"Caroline, I simply have to go," I said.

I haven't seen her since.

Perhaps it's stories like these that have me thinking the worst things are going to happen any time I get any hope. It just seems, sometimes, that it's not in the cards for anything to work out for me.

Well, this year, I'm not going to assume the worst possible outcome. I'll try to deal with things as they come. Not every situation will turn out like my botched porno purchase attempt. And, I'm a lot wiser these days. I just need to believe that. So, remembering these kinds of stories is what kicked off all of my resolutions I'll cover in the next post.

What kinds of silly mistakes or bad luck when you were younger formed your dating attitudes? Do you sometimes feel like luck and destiny are against you? Have you been able to put these experiences in perspective so that you can learn from them and adjust your thinking so you can be more successful?

What do you think?

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