S: It's On Now or Playing for the Celtics

Cheer loudly for me, Dateketeers…I have my first Date of the Month Club date all set and ready to go.

Truth be told, I had this one set up just a few days into the New Year. I’m thinking, “Man, I’m rocking this already!” Except, of course, I have no idea what I’m doing. No, seriously. Clue-to-the-less. In fact, I had to ask the other girls if this actually counted as a date.

You read that correctly… I don’t even know what a date is! It’s gonna be a long year, I can tell that already.

Anyway, it’s all set up. Too late to turn back now. But that's ok. We’re just going to grab a drink. Cool, casual, happy hour. No biggee. I’m fine. Really. I can totally handle this. It’s like I’m Larry Bird and dating is my Garden. Slaaaam dunk. (Oooh hey…Larry Bird…Crap. It’s too bad Larry Bird isn’t available. Damn the luck.)

Riiiight. To begin with, I’m already a little nervous about this. Mainly because I met this guy about a year and a half ago when we were at the same group lunch with a random mix of mutual acquaintances and I recall not being interested in him at the time. And even now, I do not actually find myself much interested. Not that he doesn’t seem like a datable guy. It’s just that our minimal, digital communiqués have lacked luster and have not led me to desire further conversation other than out of a sense of curiosity.

But, that’s the point of the challenge, right? To go out with people I wouldn’t have maybe gone out with in the past. To see what happens. Even if it’s nothing.

Ok, but then who pays? (Yes, I’m that date-tarded.) I mean, he suggested the get-together, but I’m not sure if he was thinking “date.” Do I let him pay even though I don’t think I’m interested in this going beyond the grabbed drink? Is that wrong? Do I suggest we discuss it on the offset or would that seem pushy and uptight? Do I just wait and see what happens, even if that causes an uncomfortable moment or two and ends up with me seeming to be some kind of drink moocher? Or do I jump the gun and get my guilders out right away making it clear that I sympathize with the Dutch people, even if that makes me seem aggressive and assertive?

I just don’t know.

Anyhow, for the sake of getting on with it, let’s say we successfully navigate past the “who pays” booby trap. What next? (Besides ordering the drinks, which I happen to be quite adept at.) I may have met him before, but I don’t know this guy but at all. What if we have nothing to talk about? What if we disagree on everything and it just gets really weird? What if I get all awkward and talky and continuously put my foot in my mouth? What if I’m still not interested, but he asks for another date? What if he wants to extend the date beyond the drink, but I don’t want to?

So many questions I should not be asking at my age.

And this is why I am doing the challenge. This is not complicated stuff. I just need to get more comfortable with these situations. I need to get better at socializing like a grown person. And, to be brutally honest, I need to get better at rejecting people.

I don’t know how to refuse a date without getting all stuttery and awkward and stupid, and making it a way bigger deal than it really is. I need to figure how not to just keep hanging out with someone because they’ve asked me to and I can’t find the gumption to let them know my level of interest may not quite equal theirs.

That gets me in trouble. And it is not the spinster way.

So, let’s practice…

Mr. January: Well, I had fun. I didn’t even mind that you demanded that I pay as soon as we walked in the door, AND made me sign that notarized affidavit promising as much. It was quite endearing really. Would you like to do this again sometime?

Moi: Well…uhhh…uhhh…ahem…Sure. Love to! I’ll mark you down here on the 10^th of Never. Right after my tongue piercing appointment. (gulp) You're the best ever. Maybe we can get hitched.

(end scene)

No? Not good. Eh. What the hell. At least there will be drinks. And maybe Larry Bird will show up.

Wish me luck!