Chai.

Up until two years ago, I was never the girl that got asked out. I wasn’t even the girl that got checked out. I was the invisible girl. I apparently was wearing a “Harry Potter” cloak that didn’t make me invisible to everyone, no, no, it was far more specialized than that. It simply made me invisible to the male species. What a wondrous cloak indeed! As a result I’ve carried around that alter-ego all too willingly and all too diligently.

I still have yet to get used to the idea that men are attracted to me in any way beyond common, casual friendship. I’m not saying that I walk out my front door and am immediately bombarded with desperate confessions of love or pleas for just “one chance.” What is more my reality is a couple handfuls of, “So, hey…would you like to go out sometime?” Which for me, is just as complicated as anything can be.

If I’m being honest here, which I so embarrassingly am, when I get asked out my first inclination is to think, “Is he serious?” I realize we are far past the age of asking people out as a practical joke, but I think since I missed out on the whole dating world when I was of that age, it still lingers. The thought that then immediately follows the “Josie Grossie” in me is, “He just wants to hang. Buddy-buddy style.” So I say, “Sure,” smile and beep-boop-boop-beep my number into his very available phone and call it a day; another buddy to add to the list, “Score!” And while on more than a couple of occasions I’ve found out later that, “buddy-buddy” was not the style in which the other was hoping things would be dressed, I continue to assume the very comfortable, always in fashion “buddy-buddy” thing that’s all the rage. I know…I walk a very fine line of complete dating disaster and insane embarrassment.

I wish I could say I’m getting better at it, but I can’t; not yet.

And the delicious seasoning a’top this “disaster especial” is the fact that I very often (read, almost always) give so many mixed signals and confusing clues that I can name at least two men that I have caused serious distress and discomfort. And while two may not sound like too many, when you take into consideration that I’ve only dated six men (and I’m not talking seriously dated, I’m talking even just the “one daters”) it seems to be a little more serious than, “just two.” What am I doing?

I think what has happened is that I’ve become so accustomed to just being a friend, that my natural, most comfortable inclination is to just assume that position, right from the get-go. It made never being the girl the boys sought after a lot easier to deal with; if I made them a friend first, I’d never suffer the stinging pain of rejection. And that process was mostly successful during my dating dry spell (see: my first twenty four years of existence) but now it’s mostly just throwing wrenches in all sorts of systems.

My main question (aside from wondering why I insist on being such a staunch masochist) is how do I break the cycle? I mean, it seems easy to just say I’ll not assume friendship right off the bat when faced with such situations, but let’s face it, my friendship machine is a well-oiled one. So what do I do?

Do I practice the fine art of casual dating? Always say yes then proceed to be wined and dined, ooh’d and aww’d wearing my very best “not your friend” outfit? Do I simply assume that everyone who wants to “go out sometime” or “hang out” or “meet up” (all phrases that I’ve personally been left to decipher in my dating mishaps) doesn’t want to be just friends? How do I change the course of my ridiculously misled dating vessel?

Or is Dating Disaster my final voyage?