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The Art of Owning Awkwardness…

Jimmy Kimmel and Sarah Silverman are Awkward Exes

I'm not a master of many things, people. I'm not! Though, the argument has been raised that I am the master of inappropriate ill-timed humor; they say I'm the master of having weird, gross, and sexually explicit content on my computer screen at the most incriminating moment. I am “the Most Idiotic Man Alive.” I have a penchant for doing uncomfortable things… Why? I trace it back to some good solid advice my best friend's father in law gave to me some years ago.
Esteban was his name and he found me cowering in the corner by his chimney, during a graduation party that my ex-girlfriend was in attendance for. I didn't want to see her. She broke up with me and promptly began dating a good friend of mine. I wanted to turn into a puddle of ooze and leak through a floorboard and out into the ocean where I could pollute the ocean and kill some baby seals… Of course, this ability does not yet exist; I'm waiting for Google to develop this super fly ability! Esteban said to me, “Now, Alex, you've lost a valuable opportunity.” I looked at him with my befuddled look, which is also my default look… Esteban continued “Alex, you see, you've missed the opportunity to say “hi.” I really thought he was dumb or brain damaged in some way. He continued to explain that the golden opportunity I missed wasn't necessarily saying “hello” it was saying it first. Still, I didn't understand.

It wasn't until later that I understood what Esteban meant (by the way, this dude's name is Steve, not Esteban, I just like ridiculously improbable names you would never find in my social circle), he meant that when a moment of awkwardness arrives BE FIRST! Being first is important for a number of reasons. The number one reason is that no one remembers who is second, being second is forgettable… Which is why I always climax first (sex is a race to the finish line, no?). Seriously, though, be first to confront awkward situations head on. Even if you make an ass out of yourself, be aggressive, put yourself in control and, then, take a deep breath.

After I finally returned to the One Ring to its fiery-molten resting place, with my home boy, Frodo, I understood how I could use Esteban's advice. There are women I've dated that remain in my social circle, regardless of how little I see them now, there were moments of awkwardness. I graciously stepped forth, said “hello” and gave a hug and then I was done.

Keep in mind, this tactic, being first, doesn't just apply to saying hello to a past flame. It applies to many other areas of life. Karaoke. Who has two thumbs and is willing to rock Puff the Magic Dragon in ways it was never intended by being first on the mic? This guy right here!

One of the great parables in life is to make friends out of enemies. Let's make friends with awkwardness; it promotes strong healthy bones and can get you laid… Or slapped. You decide!

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Alex is the founder and managing editor at the Urban Dater. Alex also runs: DigiSavvy, for which he is the co-founder and Principal. Alex has a lot on his mind. Will he ever get it right? If he does, he'll be sure to write.

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  1. I wouldn't call myself an awkward person but I do embrace those awkward moments. Although, I can be pretty inappropriate and sometimes that's awkward…..

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