Not One, But TWO Dates

It’s a new year, and in the spirit of starting off on the right foot, one of my resolutions is to meet more people. I’m off to a good start with two dates in the next week!

The only problem is that both guys asked ME to pick the place….grrrr! Generally speaking, I really prefer that the guy choose the location for the first date a) because even though I always offer to pay, typically I expect him to and want it to be somewhere he’s comfortable doing that, b) if someone suggests something that’s not your run-of-the-mill activity like ice skating I’m immediately smitten, and c) I apparently don’t get out enough in Chicago because I still struggle to suggest where to go for a drink, beyond the couple spots I got with co-workers.

If I was in DC, this wouldn’t be a problem. Four Courts was my SPOT. The Irish pub was perfect – busy enough that you didn’t feel weird, but quiet enough to hear each other talk. And, most importantly, they served Strongbow, my fave drink of choice!

Funnily enough, I’m pretty sure I was introduced to the place by a guy that picked it for our first date back in the day, but I quickly adopted it as my own.

In Chicago, though, I’m at a loss. If we’re meeting after work, it’s easiest to stay downtown but other than Jake Melnick’s and Mike Ditka’s, both of which are literally around the corner from my office, I just don’t even know what the options are…which ultimately ends up revealing to potential dates just how little I’ve been drinking lately. Ugh.

On the plus side, according to one of my upcoming dates, my lack of knowledge about the downtown area isn’t surprising.

“Bars downtown close at like 9 no one hangs out in the loop area,” he texted (lack of punctuation and all).

So guess I’m excused there! But, my other date suggested I pick a place near where I live in Lincoln Park – which is even worse! I know the couple bars near my house where I can grab a beer, but I have no idea what the “cool” places are to hang out, much less what would be a good spot for a first date.

The worst part is, the location can set the tone for the entire date. And not only that, it’s going to give them an idea of where I hang out (or more likely, where I’m clearly NOT spending time), allowing them to judge me before we’ve even got a beer in front of us.

Dating has become so fraught with pitfalls! If you’ve got any ideas of places that I could turn into my new first date place, PLEASE send them my way!

On The Prowl Again

That's right, I said it - I'm ready to do some man-hunting! Granted, it's been awhile and my instincts may be a little rusty, but I'm ready to put them to the test.

But hold that thought - first, you have my sincerest apologies for the months of silence. Turns out that getting acclimated to a new city takes a lot out of you, and when I can't blog at work anymore - because I actually have WORK to do - it's a lot harder to find the time to write!

To bring you up to speed since I last filled you in, sadly, things with DMV Boy did not have a fairy tale ending. Sadly, DMV boy did not turn out to be a match made in heaven. As lovely as the story was of how we met, it just wasn't meant to be. He DID call (call, mind you, not text!) and we hung out several times - he even made me dinner and scored us tickets to Conan O'Brien's writers' show last fall. In the end, though, he was just a little too vanilla/Minnesota nice. I know - sounds horrible, right? I'm NOT looking for a bad boy! But unless there was alcohol involved, the conversation was far from scintillating, and when added to the fact that it took 45 minutes to get to his house on public transportation, I decided to cut my losses sooner rather than later. He remains a gchat friend, but we haven't met up in awhile.

Since then, a lot and yet nothing at all has happened. I'll let you in on a secret - one of the perks of leaving DC (in addition to an amazing job opportunity and the chance to live in the Windy City) was leaving behind a bit of heartbreak. A drastic change of location certainly helps a girl move on - until the boy in question suddenly reappears again. Too make a very long story short, a relationship I thought I had left behind with all my furniture and other castoffs turned out not to be as over as I thought. Unfortunately, although this boy is someone I now consider to be a very dear friend, he remains the object of some unrequited affection. And although I've done my best to convince him otherwise, repeatedly stressing how CRAZY he must be for not wanting to give things a go, it's time to truly leave the past in the past.

Which leaves me ready to take Chicago by storm! To that end, I'm meeting and greeting all over the city. To further hedge my bets, I've also joined Match.com again - after all, 1 in 5 relationships now begin online (or so their ads proudly proclaim!). At the very least, I'm hoping to expand my circle of Midwestern friends. Although I love my co-workers, a girl occasionally needs some non-Type A, less than uber-organized, self-professed "not" planning fiends to hang out with on the weekends.

So keep reading in the coming months for what are sure to be some hilarious dating stories:).

Friends...or More?

I moved to the DC area three years ago not really knowing anyone. Sure, there was the odd acquaintance who was a friend of a friend or my mother's cousin type of thing, but for the most part, I was on my own.

Until I met my friend Charlie*.

We ran into each other for the first time at Clarendon Ballroom while I was waiting in line at the bar. He was with a bunch of guys, and as I stood behind them, he introduced himself by offering to buy me a drink - if I'd give his friend a birthday kiss! I laughed, but his smile was so adorable and the pick-up line so original, I ended up talking to him for the rest of the night.

At first, we flirted with dating, but it just didn't seem right. Instead, we started hanging out occasionally - platonically. Over the next several months, I started to think of him as one of my best friends in DC. Everything was just so comfortable - we'd watch movies, make dinner and spend most weekends on the golf course. If I was over late, it was easier to just crash at his house than go home to mine. He was my Dawson - with some casual benefits thrown in on the side if neither of us was seeing anyone else (so maybe it wasn't entirely platonic)!

About a year ago, we started circling around the idea of dating again, but neither of us was willing to say we were interested in the other. And then, one day, Charlie suddenly had a girlfriend and dumped me as a friend.

"I thought it would be awkward for you," he said. For me? Why? We'd always been buddies more than anything else - it didn't bother me that he was dating someone other than me, but I was incredibly hurt that he didn't want to spend time together anymore.

We crossed paths a few months later at Sign of the Whale during Nightmare on M Street. He was dressed as a cow (I was Jem from Jem and the Holograms), single again, incredibly drunk and out of nowhere asked me why we were never a couple. "We would have been perfect together!" he said.

WHAT?! Where did that come from?

I was seeing someone else at the time, so nothing came of it then. And it took me several more months to get over all the anger I felt about the way he severed our friendship. But then, a few weeks ago we were hanging out late one night and suddenly I felt differently. Not only was I having fun, but I wanted to jump the guy! (Something of a 180 for me - I've always thought Charlie was really cute, but the spine-tingling feeling was always been missing before.)

Over the next three weeks, I tried to tell Charlie that I liked him. There were going to be no missed signals this time around! But something always came up and the timing just didn't seem right.

Then this weekend, as Lauren and I made mac and cheese after a night at Clarendon Grill, we collectively (and intoxicatedly) decided it was a GREAT idea for her to repeatedly call the guy she's seeing and for me to text Charlie my epiphany.

"On the off chance u haven't figured it out yet, i have a crush on u...just wanted to lay it on the table:)," I punched into my phone and hit send, before I could change my mind.

No response that night.

When the return text did come the next day, there was no reference to the baring of my soul (Ok, that's a little dramatic. I was actually somewhat indifferent at this point, but firmly believe in putting everything on the line so that I walk out of every situation knowing it's not my fault it didn't work).

So I texted again. A very, very long text. Which, of course, then encountered technically difficulties in getting through, so I had to split it into three separate messages and send all of those. His reaction? "I'm at work. I'll call you later."

That was Sunday. I'm thinking he's probably not interested, but the worst part is, who am I going to play golf with now? At least with Charlie, I could always be assured of winning and never had to worry about a bad shot because it was almost guaranteed his ball would be further in the woods than mine!

*Name changed in the event Charlie finds out about this blog - although, he should recognize his role in this tale!