Last week I wrote about modern day matchmaking. Which led me to thinking that I just might need a little help in the dating world. Not only did I reach this conclusion after my wonderful encounter with creepo Tim, but the last date I went on pretty much affirmed it.

This date was a while after the whole Tim fiasco and after my initial scare, I was back to thinking that I need to get myself back out there. (Out there meaning the dating scene, of course. Whatever that means...)

(Dramatization)

So I'm just hanging out with my friends on some random Saturday night and Jacob, a frequent face at the bar we hang out at, sidles over to sit by me. Jacob is a harmless Italian barfly who I have had many a conversation about Lost with. This alone would normally be enough to woo me, but truth be told nothing about Jacob had really appealed to me. I don't know why. It could have something to do with the fact that he dressed up as Amy Winehouse last Halloween. Men in miniskirts have never quite been my thing.

After he sat down, I found out that it turns out he is fond of me! He said so himself. Just like that. He then asked if I'd like to go out sometime. I of course was flattered, and despite the fact that I was not remotely into him, I agreed. See, he is somewhat devastatingly attractive (when he is not in full Winehouse garb that is,) and I really wanted a nice night out!

I (stupidly) agreed to the date on one condition: I would only go out with him if he remembered to call me the next day. You see, he was drunk as a skunk, and I was positive he would not remember the conversation in the morning.

He then handed me his shiny iPhone and I put my number in, slightly wary. The thing is, while I have always thought that Jacob is a nice sweet guy, I never saw myself dating him and I didn't want to lead him on. So technically speaking, I should have really refused his offer, but I was positive that he would not remember any of it in the morning, and hey, that way his drunk ego could remain intact.

(As you have probably gathered by now, I am very sensitive to the male ego. One of my many issues.)

The next day I got a call from an out of the area phone number which I normally wouldn't answer, but I am into this whole new positive thinking thing, and I realized it was obviously my boss calling to tell me about my new promotion! I answer.

"Hello?"

"Hey Natalie, its Jacob."

Oh dear, he remembered.

"Hey, so remember what we talked about last night?" (Of course I do, but how does he?)

"Um, yeah."

"So when do you want to go out?"

I've done it again. I've gotten myself into an impossible situation. But I have no one to blame; I did it to myself. Never make a deal with a drunk person. That is my lesson, or rather it should be. Don't make plans you don't want to keep. But here I am.

"OK... yeah let's meet up later in the week." I say, hoping he has a full schedule.

"Thursday?" he replies.

Wow that is actually my only day off this week. Crap.

"Yeah, OK sounds good." I lie.

You think he would pick up on my not so enthused voice. I mean if he was a girl he probably would have noticed the tone (girls always notice tones, it is our superpower.) If he was a girl he would have realized I was less than thrilled about our 'date'. But he isn't, and he didn't. He said he would call me later to finalize the details.

Yay.

I'm telling you at this point, my conscience was eating me up, I mean I really don't see this going anywhere. And I am not a serial dater. (and thank God I am not, otherwise I can only imagine how many blogs I would have to write.) I should just let the guy off easily! Neither one of us should have to put ourselves into this awkward date scenario.

Thursday arrives. I head over to meet him at Starbucks. Otherwise known as the romantic hub of lovers. 

Thinking about this, I realized all this ripping myself apart was ridiculous. It's Starbucks! It's not that big of a deal, its only coffee! I mean it's not a marriage proposal! And now that I thought about it, it was sweet that he liked me and maybe I should cut him some slack. Plus its free coffee, my favorite kind!

I arrive and he is already there waiting for me. It was just too bad I wasn't into him. It would be really nice if I was! I walked inside and sat down at his table.

And then I waited.

He was busy talking to someone else at the table next to him and he did not acknowledge me at first. Hrm. Ok. I 'wait' for him to finish his conversation with the pretty blond. (What is with Starbucks and Kate Hudson lookalikes? Can't they drink coffee elsewhere? Like in a cave?)

Belongs in cave

Jacob suddenly notices me. He leans in, smiles at me, holds out his hand... and slides me a Starbucks gift card. "Here, I got this from work, go get yourself something." He then turned to his iPhone.

Wow. Well, I'm sorry, but if you are trying to woo me, this is not how it's done. I do not blame him for talking to the chick, nor do I mind his obsession with his phone (that much,) but this?!

I mean, even friends don't treat each other like that! In fact when I get coffee for my friends I stand in line with them and let them order and then cheerfully pay for our lattes. It's just how it is done! It's one thing to stand in line and offer to pay for your dates drink, but it's another to slide some money over on the table and tell me to get whatever I want. I mean that's something my Dad would do.

I should have looked him in the eye and said, "no it's OK, I can mange with my own money!" But I was so irritated I figured I deserved a free cup of coffee. I stood up in a huff and then he gave me a genuine smile. Oh no. Not again.

My beautiful compassionate side returns. I get it. He is obviously shy. This is probably how he shows that he likes me and thinks I'm pretty! Rabid feminists have probably scarred him in the past when he tried to pay for them!

I go to the line. It is long. Ugh. Who cares if he is shy? (How is it possible for one's mood to fluctuate so quickly?) It's not my fault. Standing in a line on your own while your date talks to an aspiring Hudson'esque model and her gay husband is depressing. In fact, it's just plain old sad.

My sadness caused me to order the largest most elaborate drink I could fathom. Upon my return, I see the party at the other table have left, and I decide to start over. I am determined to have a good time.

But as they say, it takes two. From here on, the whole evening seems a bit awkward. I have to lead most of the conversation and I keep trying desperately to make eye contact with him, but the fact that he is sitting sideways to the table looking straight ahead, makes it a little difficult!

I should probably tell you that I am usually a likable date. Unlike a lot of girls I talk about sports, (Go Dodgers!) I make a point to ask about him, his job, his family...his dog....and at this point I realize know a lot about him, but he is not making any effort to ask me anything.

I am a girl, so this leads to an immense amount of self-questioning. He must be really shy, right? Do I have spinach in my teeth? Am I not what he expected? What is the problem? We get along so well at the bar!

Then I realize.

This is the only time we have ever been together when he has been completely sober. That must be it, I tell myself, he has no liquid courage in him! He IS shy! (I hope.)

But perhaps he is a shy...alcoholic?

Great, I think. I'm only attractive to men when they are intoxicated alcoholics.

"Well this has been fun!" I lie.

"Yeah, we should do it again soon." He lies back.

We shared an awkward side hug and parted ways. We haven't been out since.

I of course started obsessing about whether or not to return to the bar (one of my regular hangouts,) because of fear of awkwardness, but eventually gave in and sure enough...there was Jacob when I walked in.

....

As I said...We haven't been out since the icy date of doom.

But there is definitely a part two to this story. It involves a rainy night, more alcohol and a declaration of love.

Till next week then?

<-- Read Natalie's previous blog 'Gentlemen Prefer Blondes'
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