Thursday, November 16, 2006

From the files of "Why do I try?"

More reasons why I hate dating. No, correct that, this, this isn't even dating, this is an attempt to communicate like a human being instead of a machine. And still I manage to come across looking like an ass.

Here's the setup: there is this guy in one of my classes who is totally adorable. From the very beginning, I've had an innocent little crush on him. When I found out we were interviewing for the same company, it fueled my interest even more. I made a promise to myself that I would use this knowledge to speak to him in class.

I'm such a chicken shit that I couldn't do it.

So last week, at an event, I found out from an alumna that the cute boy was also invited down for second round interviews at the aforementioned company. This was my in!! Surely I could talk to him now about it.

But no, I still couldn't. He even sat one seat down from me in class and I found myself hopelessly mute.

Finally on the trip, I decided I had to make some conversation. Waiting for the plane on Tuesday, I chit-chatted with him briefly. It wasn't like there were sparks flying, but it was nice, introductory conversation. He recognized me from the class, we talked about how much work we have to do, he told me about his last trip to Louisville (our destination).

The rest of the trip, we were in separate groups, so I didn't have other chances to talk to him. Last night, I briefly tried to talk to him, but he was engaged with one of the executives and I didn't want to intrude. So I said nothing.

At the end of the night, once we all arrived back in Chicago, we piled into two limos. Standard--I was in a different limo. But his gift bag from the company somehow ended up in MY limo. Since I have class with him, I (shamelessly) offered to return it to him.

This morning, feeling bold (and with some prompting from OtherGus, I might add), I decided to e-mail him to let him know the bag's whereabouts. I thought it would be fun to be sassy and flirty. This is what I sent:

Subject: Hostage situation

Hi, [Cute Boy]--

Your bag turned up in the second limo... I'm holding it hostage. It's safe (for now) but in exchange for safe delivery back to you I may have to make a ransom demand.

So what's it worth to you??

Sarah
After some hesitation on whether I was being too bold, I sent it off into the Internets. Perhaps I had reason to debate. Only a few hours later came his response:

Re: Hostage situation

Sarah... thank you so much..... I realized as I got out of my Limo.

I'm away interviewing again today... I could pick it up on Monday.... do you wanna bring it to class on Monday night? Else I could walk over to Medill and pick it up?

thanks!
Oy.

I can interpret this response in one of three ways:

1. He thinks I'm an idiot.
2. He's dense and had no idea I was flirting with him.
3. He has a girlfriend.

Frankly I'm not sure I like any of those options. And regardless of what he thinks, I DO feel like an idiot. I'm tempted to leave his bag on his seat on Monday and hide in the back of the classroom...

Of course, there is also the fourth possibility that he just isn't interested and was trying to express that in a nice way. But my ego prefers to pretend that simply isn't an option. I mean, who doesn't think tense negotiations are cute??

Isn't being single fun??

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