When Dating Philosophies Collide

Recently, I met a guy. (Whew, crazy right?!).  I met him at work – he was visiting the racetrack (I work up in the press box) with a large group of his buddies.  They were enduring a bachelor party so had shimmied over on a nice little margarita buzz. He approached me and asked for my number.  He kind of resembled Sean William Scott and was super sweet, like the smell of tequila coming out of his pores on his breath.

Smitten, I scribbled it down, hoping I put the right area code. I didn’t expect him to call me that night because I was convinced he was at his tenth strip joint, but when he called me asking what I was doing my hopes took a high ride. We talked for a little bit, but his bachelor party activities got in the way of us hanging out that night (probably because he couldn’t figure out how to get a thong untied from his face).

And now, this girl needs some serious Dating 101. Unfortunately homeboy didn’t ask me to hang out/go on a date beyond our brief bachelor party convo and now all I want to do is ask him myself.

But here comes the battle of my two dating philosophies:

My Dating Philosophy #1: ‘Tradition is Key”
I’ve always been more traditional and it’s annoying. It has worked and hasn’t worked in my favor. I always want the man to make the first move, because then I can be sure he digs me.  I’ve always felt more safe that way. Why would I waste time asking questions like; “Nope, he doesn’t like me because he put his hand in his pocket and looked at the ground when he said goodbye…”

If the guy asks me out, you know he wants to see me, right?  But if I ask him out – I really don’t know for sure if he’s giving me a pity-date just because he doesn’t have the heart to say no.  I guess my pride has roped in the best of me.  We all have an itty bitty tendency to stick up our nose and bask in the satisfaction/fantasy land that I’ll be fine, the man I end up really loving will ask me out himself.

From what I’ve learned, guys are pretty simple.  If they like you, they will ask you out. If they don’t um…they won’t.  In the end, wouldn’t you want a confident guy that is going to jump forward and make the first move anyway?

My Dating Philosophy #2L “It’s 2010-You-Are-A-Big-Girl?”
What do I have to lose? You get what you want in life because you go out there and get it yourself. I’ve been riding easy on the quote, “You have to go on a limb sometimes  because that is where the fruit is.”  It really is true; you have to put yourself out there or how are you going to ever know if ‘it was meant to be.’  Besides, what is the worse he could say – ‘Um no?’ His loss anyway.  Guys nowadays like a confident girl who can bust out of the realm and ask someone out.  It is that simple.

Recently, my the other lovely intern in the press box gave me fabulous advice – and yet another great philosophy. She said, “I say you ask him. If he say’s yes and he likes you, than great! If he say’s yes and doesn’t like you? That is his problem that he has to sit through an entire movie with you.”

So true. But I’m still stuck in a rut. And the rut usually consists of staring at my iPhone screen and constantly deleting attempted text messages. Do I ask him on a date myself – shamelessly – and risk the ability to know if he really digs me? Or do I sit duck and wait for his phone call, knowing for sure that he’s into me if he does?

I need some help here! Which philosophy do I loyally follow??

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