New Levels of Awkward

Just when I think I've conquered every awkward situation possible, I find myself in the face of entirely new levels of awkwardness that I previously did not know existed.

A few weeks ago at my girlfriend S's work event, I met a guy who actually seemed really fun and interesting. When I expressed to S that he seemed cool, she thought about it and told me, "Actually I think you two would be really good together. Make that happen!"

"But," she warned me, "You need to know, he is EXTREMELY awkward"

I laughed her off, since I have a Ph.D.'s worth of knowledge on awkward men. Some people specialize in physics, some finance, I have mastered the art of loving men who can't look you straight in the eye because they're scared of girls. Fact.

So, all full of hubris that I could totally handle this, I asked Awkward if he'd want to go out for dinner sometime. That's right, I asked HIM. And then when he stuttered an affirmative, I wrote my number down on a scrap piece of paper and gave it to him.

This is where it starts to go off the rails. A few minutes later, he said to me, "Hey did you give me your number?"

To which I replied, "Um, yes, I wrote it down on a piece of paper."

He looked at me all confused: "You did?"

"Um, yes it is in your pocket."

At this point he fished it out of said pocket and I jokingly said, "Well, now forget it. I want it back!"

And the poor boy actually handed it back to me and apologized. (Yes, he was drunk, but still.)

So now I was flustered and I explained to him that he could keep it, but clearly this situation was not off to a great start.

A few days later, he told S that he'd had a great time with us and we should all hang out again soon, and then apologized because he had acted like a douchebag to her friend by trying to give her phone number back to her.

Yes, already cringeworthy, but it's about to get worse. Brace yourself.

I decided, in my infinite wisdom, that he was going to be too much of a coward to call him so I got his number from S and called himself. Which is the set up to what will go down in record as the Most. Awkward. Telephone Conversation. Ever.

After explaining that I wasn't upset about the phone number debacle, I tried to open up a conversation. I think one of my talents is my ability to have a conversation with pretty much anyone. But my conversational tactics proved to be no match against his intense awkwardness.

Not only did we have zero phone chemistry, but the constant long pauses made me so uncomfortable that I started babbling about whatever came to my mind, which really was not that impressive given that I was banging my head on the coffee table just so that I could hear something other than the dull buzz of dead silence on the cell phone.

The following is an actual excerpt from our conversation:

Me: So you grew up in San Francisco, right?

Him: Correct.

Me: Did you like it there?

Him: Not really.

Pause

Me: I actually just applied to school out there.

Him: Oh.

Long Pause.

Me: You know what's funny?

Him: What?

Me: My little sister just moved out there and you never think of a three-hour time difference as being significant, but it's actually made a difference.

Him: Really.

Me: Yeah, well we talk a lot, and now whenever I want to talk to her at 11AM my time, she's still asleep. And when she wants to chat at midnight, it's 3AM for me...

Him: Yes. That is how time zones work.

Me: Yeah, I know...

Longer Pause.

Me: Sooo...would you like to hang out sometime?

Really Long Pause.

Him: Um, I'm going out of town next weekend, but I guess I would be open to that.

Me: (confused) Ooooook.

Him: I'll, um, friend you on Facebook and we can open the channels of communication that way.

Which put an end to the most awkward hour of my entire life. That's right, this painful banter lasted a WHOLE HOUR.

I obviously called S right after and told her the whole story about how I had just gotten blown off.

She laughed hysterically and said, "To be fair, I WARNED you about him! He gives a whole new definition to awkward. He is really awful with girls. I tried for four years in college to hook him up, and he just couldn't do it. He is terrified of girls! I feel so bad for him!"

"What?!" I exclaimed, "Feel bad for me! I just had the worst phone conversation in all of history."

"Yeah, but you'll be ok. He, on the other hand, will be alone and awkward for the rest of his life. You are the only person I know who actually LIKES awkward guys and even he is too much for you, which means he will never find anyone!"

To his credit, he did friend me on Facebook immediately after I hung up on the phone. As in, he must've been sitting on his computer staring at my profile just waiting to press the "Add as a Friend" button. Which makes the whole thing even more uncomfortable.

So after all of my friends made fun of me for an adequate amount of time, they tried to console me by telling me the obvious, that I would never want to date someone THAT awkward. Which is entirely legitimate, but I'm thinking with copious amounts of alcohol, it might be actually bearable to spend time with him. But that's probably not the foundation for a healthy relationship, right?

Either way, I have found my new benchmark for awkwardness. A significant accomplishment any way you look at it.