Friday, January 22, 2010

"It's Complicated"

When it comes to dating situations, I find that not defining things is the safest way to go. That is, avoiding the labels and letting things go where they may -- at least until both parties are sure they want to be with each other.

Where is this coming from? Well, a while back I made mention of a "telephone courtship" I was having with a guy I'd met through the online dating thing. I was skeptical at first, and when we did a LOT more phone conversation than actually seeing each other, I just got discouraged. Truth is, I really did like him but if it wasn't moving ahead, then why get invested? And, our distances and demanding work lives did nothing to help the situation.

So, I moved on. Sure, I talked to him, but I didn't focus on being with him so as to not drive myself crazy. Heck, we'd tried to get together on multiple occasions, canceling on each other, picking mini-fights when one bailed on the other... What's the point if we can't make it work?

But then we started talking again. And he -- who we'll call Sean -- ended up telling me that he was bummed about how things went and that he really did want to try things out. And, thinking I had nothing to lose (while recalling how I did feel about him) told him I felt the same. And we started making plans again.

Fast forward to early this week. Given the business holiday, he ended up coming in over the weekend for his birthday. We ended up painting the town red with some drinks, laughs, flirting, professing the feelings of "like"... And then, well...

The following day, we spent a lazy day together, ordering take out and going out for sweets... I mean, if I didn't know better I would have sworn we were a couple!

Now, I'm also something of a realist, and aware that taking it to bed does not mean insta-relationship. But, given our history... Well, it becomes more than a casual romp session, which therefore makes it a little more complicated.

I haven't done the overly-girly thing and talked to him about what this means - mainly because I'm not ready to define it. But, off the bat, I'd say it just got a little ickier than your average hook up.

But, here's where I put a halt to my "analysis" of the situation... What's going to be will just be, right? Right?

Well, time's going to have to help with that one (As if I don't have my hands full already, right?). But I can tell you I won't be changing my Facebook status quite yet.

Wednesday, January 20, 2010

The Hook Up Game (A Saturday Night Tale)

So as it is in the world of dating, the last few days have been a whirlwind and filled with stories. But, since I can only tell one at a time, I'll share this experience/encounter with you.

Warning: Unlike many of my posts, the lesson here is not bundled neatly at the end of this post. Well, not quite. This post is much more for entertainment purposes.

This past Saturday night, I was out for Marisol's birthday. If you've been reading past posts, you'll know she's a partner in crime and I find that my most colorful and entertaining stories happen when she's around.

But I digress. We ended up out in a trendy part of Chicago, spending much of our night at a popular karaoke bar and not leaving until they were closing some time around 3 a.m. While waiting outside, we saw two guys just randomly hanging out as though trying to decide what to do next. And that's when Marisol decides to flip the script:

Marisol: Are you guys single?
Both Guys: (In unison) Yes.
Marisol: Good. Then you're coming with us.

And like that, we'd adopted these two guys, headed to another all night bar in the area. Shaking my head, I was curious to see how this would all unfold.

Meanwhile, our other friend Caroline had hit it off with a guy at the karaoke bar. He was extremely attractive, and that seemed to be a pretty locked and loaded hook up (I found out later that it worked out quite well for her!)

Anyway, in addition to Caroline, Marisol and I were with Shelly, one of her other colleagues. While Shelly had been playing it neutral at the karaoke bar, she arrived to the second bar, ready to go, and immediately capturing the attention of a handsome, well-dressed man in the corner who had his eyes on her. Soon, they proceeded to get quite cozy on the couch, long forgetting that they were in a booming crowded bar on a Saturday night.

So here are my friends, Marisol, Caroline and Shelly, all with good-looking men, and making love connections in a matter of minutes. Granted, connections like this aren't usually considered ones with the greatest chance of success (unless of course, you're the "exception to the rule," in which case we can debate that one for a while), but it was fascinating to see how these couples gravitated towards each other rather quickly.

As for me? Sometime in between Marisol engaging with one of the karaoke boys and Shelly engaging with Mr. Handsome Man, I spotted a very good-looking man, Jonathan, in the corner, having a drink alone. And, armed with my new motto of just going for it, I decided to approach him to see what would come of it.

We immediately traded a host of light-spirited jokes and comments, and I quickly realized that he was quite sharp and worth paying attention to. And, when I told him (honestly) that I was initially concerned about approaching him because of how he'd respond to me he impressed me with a simple response:

Me: Glad I came over. I was a little nervous about how this would play out and what you'd think.
Him: Well, you're here now. Let's not over-think it and see where it goes. But you've already got my attention.

And that was it. Just like that -- if he didn't have my full attention before, he did right after that statement.

We traded numbers and are currently in the process of making plans to get a drink sometime. What will come of it? No clue. But to take his advice, I'm not into over-thinking it at this point. Just taking baby steps at the moment and letting the chips fall where they may. But if he calls, I'm listening.

Moral of the story? (Oh c'mon... You didn't know I'd try to sneak this in?) Saturday nights can STILL make for the best stories... And I plan to continue enjoying that as much as I can!