Ski Trip!

Ski trips and I have a great track record (see "Leaving on a Jet Plane" - and there’s a lot more to that story than what’s posted), and for the last year I’d been looking for a buddy to join me in hitting the slopes with one of the local ski clubs in Chicago (yes, I hate doing this kind of stuff alone, which is why I had to find a friend to go with me – and lost a year of skiing in the process!).

Luckily, my new running buddy likes cold-weather sports, too, and we couldn’t wait to spend a weekend at Granite Peak with a bus-load of what I was sure were going to be new lifelong friends!

We boarded the coach bus on Friday night, armed with a bottle of wine and several beers to help us survive the 4.5-hour ride to the “mountain” (it’s the Midwest – we use the term loosely around here).

I didn’t want to be overly pushy as I made my new friends, so we chose a seat toward the front figuring we’d have all weekend to get to know people. What we DIDN’T know was that the six middle-aged couples surrounding us were going to be the rowdiest crowd on the bus – and by that I mean DRUNK. No doubt if we’d been at a bar, I would have thought they were hilarious, but in a confined space the 50-something guy that was going up and down the aisle to hit on girls while his wife yelled stories to anyone who would listen rapidly lost its amusement factor.

Somehow, Kelly and I managed to make it to the hotel without bitch-slapping anyone, and piled onto the elevator with all our gear…and three very cute boys!

“Party in room 327,” we called to them as we all separated down the hallway, and as an aside I told Kelly, “THAT’s who we’re hanging out with this weekend.”

We were slow to get moving on Saturday, but that was ok since we had big plans for the evening. Once we got to the lift, we spent some time getting our “ski legs” on the bunny slope, before bouncing around the mountain with several pit stops for beer and hot chocolate – I forgot how COLD skiing in the Midwest can be.

All in all an uneventful day until it was time to après. Kelly, being the social butterfly she is, conveniently snagged us a prime viewing spot in the bar next to a friendly older gentleman we could chat the time away with until something better opened up.

An hour later, we were comfortably ensconced at the same table as a group of guys (NOT the same as in the hotel – we’ll call this Group #2) we’d been eyeing earlier in the day – at the time trying to figure out why they weren’t eyeing back. Turns out, they were much friendlier after skiing, and we were quickly fast friends.

In the interest of transparency, I should probably mention that I think they were all about 22, but we weren’t exactly being picky at that moment! As we continued to flirt, I was itching to do a couple night-skiing runs, but Kelly was done for the day and these guys all had their boots off.

Lucky me, but who should I notice at the table next to us? Group #1 of guys from the night before – and they’d been joined by the guy that I’d thought was VERY cute on the bus. Even better – their boots were still on and I was a few beers in, which allowed me to casually invite myself along for their next several runs. By the time we hit the lift, we were all fast friends, and becoming even more so thanks to an illicit bottle of Jim Beam.

After an exhilarating hour of buzzed skiing (don’t try this anywhere but the Midwest!) and chatting up my new friends, we all headed back to the hotel where it was time to hit the…you guessed it…HOT TUB!

Kelly and I headed down, well swaddled in our towels to limit the view of our shark-bait-white bodies, and slipped quickly in the wonderfully warm water. The numbers were in our favor –did I mention that we’d invited Group #2 back with us??? – and we were quickly SURROUNDED by boys. Yep, us two girls and eight guys in a hot tub that has a capacity limit of eight. BIG SMILE.

What’s not to love about this situation? Just one thing – it was decision-time. With so many choices, who should we cozy up with? And this was where it got a bit tricky – Group #2 were headed back to Green Bay that night, but they also seemed a bit more interested. On the other hand, Group #1 had long-term potential – these were my new lifelong friends who I wanted to spend every weekend skiing with!

Ohhh, the pros and cons of each – and trying to weigh them after several sips from that pesky Jim Beam bottle!

Luckily, it was easy to immediately rule out one of the boys from Group #2. No boy over the age of 12 should be seen in public wearing bikini briefs – even if they are black rather than the oh-so-not-attractive tighty whitey variety! Ugh – I’m still grimacing at the memory.

With options narrowed down, the choice was eventually made when one of the boys from Group #2 settled in next to me in the hot tub and quickly got cuddly. Remember – only 22, but I wasn’t being picky! Things were getting a bit steamy in the testosterone-filled tub so I hit the pool to cool off and the boy followed – along with his other friends, including Bikini Briefs.

At this point, things somehow deteriorated into a bellyflop contest, once Bikini Briefs demonstrated he didn’t know how to do one (a demo I certainly DON’T want to watch again). After sharing my own spectacular technique, I found myself in the arms of the cuddly one from the hot tub, and next thing I knew we were enjoying a very nice, PG make-out session.

After putting on a show for a minute or two, I looked up to see that Kelly was making her own luck with one of the boys from Group #1 – she definitely chose better than I did, as the following day she had a nice cuddle-buddy on the bus back to Chicago! Apparently, though, I left the cuddly one grinning ear-to-ear. Kissing is so much fun!

Finally, Group #2 decided to pack up and head home – and I wasn’t exactly sad to see them go. For one thing, I did not want to deal with the awkwardness of them hanging around all evening! And for another, I did NOT want to discuss sleeping arrangements later. Making out with a 22-year-old, yes, other stuff – not so much. Turns out, though, they left because the boy Kelly was talking to “killed it” for them – they couldn’t deal with the competition! Hilarious!

All in all, a very successful ski trip – and the slopes weren’t bad either!

Talking vs. Texting

It’s no secret that new technology has caused the rules of dating to change. From Facebook stalking to texting, we’re a long way from “courting.” Although it’s not one of my favorite movies, there’s one scene I love in “He’s Just Not That Into You” where Drew Barrymore’s character wonderfully illustrates the change in dating as she bemoans the use of Myspace, Facebook, voicemail, email and all the other new modes of communication.

In theory, a guy definitely scores major points for calling, rather than texting. But, here’s the thing - I LIKE texting. Especially when it’s someone I don’t know very well. Since I’ve moved to Chicago and no longer spend an hour a day commuting, I talk on the phone a lot less – to my BEST friends. Why would I want to spend what little time I have making awkward conversation with someone I may not have even met yet (at least not sober)?

In my mind, texting is like those little candy hearts people give on Valentine’s Day – but all year long. It’s a quick hit to let someone know you’re thinking about them – which will put a smile on my face for the rest of the day – without having to find 30 minutes to chat about the weather. Don’t misunderstand me – texting should NOT replace the phone, but I think it’s a nice, flirtation complement to more traditional modes of communication.

This topic came up thanks to one of the two dates I mentioned in my last post. We connected through Match.com right before Christmas, and due to holiday schedules made plans to get together once things had died down. After exchanging a couple of emails, the guy suggested I give him a call. WHAT?! How forward!

First of all, I’d made the initial contact, so if anyone was going to make calls, it should have been him as I’d already stepped up to the plate. Secondly, talking to a stranger I hadn’t even met while at my parents’ house? Ugh. Thirdly, weren’t we both busy enough with family obligations that week?????

And finally, and most importantly, why would I want to invest the time in phone conversations when I knew there was a very good chance I’d meet the guy in person and realize immediately that I’d be counting down the minutes until I could gracefully end the date – never to speak to him again?

Pessimistic, yes, but also realistic. It’s not that I didn’t hope that I’d want to hang out many, many times after I met the guy, but based on my track record with Match.com dates, I knew this was unlikely – at least, enough so that I no longer want to put too much effort into things before the first date.

In any case, I did NOT take him up on his invitation to call, and the week after the holidays found us setting up a time to get together. At this point we did exchange a couple of texts about meeting details, but sadly, nothing flirtatious happening there – just straight coordination.

The day of our date finally arrived, and I actually went to the trouble of putting on not only my usual make-up, but even eyeliner! At this point we’d been talking via email for about three weeks, and to be honest, most of the excitement for me was gone. I’m all about the momentum in new relationships, and felt like it was long gone, but I was ready to start 2012 off with a bang and was certainly happy to be meeting someone new.

Except he canceled! Three hours before the date! He begged off claiming he was stuck at work, which didn’t bother me at all, as I’m guilty of that far more than I should be. BUT, he said he’d call that weekend to arrange another time – again with the phone call! Apparently, I wasn’t going to be able to meet the guy without talking to him on the phone first.

Turns out my anxiety over making small talk was all for naught – because he NEVER called. All that effort in emails and making plans…all wasted. Good thing I didn’t make a point of finding the time for a few awkward phone calls!

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!

A Different Breed Of Men

In a recent meeting at work, someone described the social media voice of a client as a Midwestern cross between the Brawny man and Conan O'Brien – except, apparently the client disagreed with the picture that was presented. Supposedly, the strapping young men in the area aren’t as attractive as what we put forward.

To which I thought, “WHAT?!” Who wears flannel better than a homegrown, boy-next-door type from somewhere in the Minnesota, Iowa and Illinois triangle? (As a random side note, check out one of my favorite YouTube videos here, in which flannel is prominently featured during a parody of Katy Perry's California Gurls.)

However, the client had a point - there does seem to be something a little off with the boys in Chicago. Specifically, a lack of interest in girls. Or at least me!

In an attempt to meet new people when I first moved here last year, I quickly joined Match.com - but despite dozens of winks and emails to the "supposedly" eligible bachelors (I'm convinced some of the better-looking possibilities are actually dummy profiles that have been planted to help keep you interested) in my area, I ended up with only a single date over the course of a month. Some of you may think this is all that can be expected from online dating, and that in fact, a single date with a decent guy in four weeks is actually a good track record.

However, I know better. When my roommates and I were at the height of our Match.com-ing in DC (think Monday nights spent on the couch with our laptops open to better compare potential matches while watching The Bachelor), I would occasionally have two to three dates - per week!

At the time, I chalked it up to the fact that we were in the middle of the holiday season. After all, from a strategic perspective, who wants to risk the possibility of having to Christmas shop for someone you've only known two weeks?

But now that it's August, and I'm having the same problem, I realize there must be something more going on. You could make the argument that during the summer, everyone is out and about happily meeting (and hooking-up) easily enough between happy hours, weekends at the beach, etc. Except that summer is winding down, and still no uptick in dates. And it's not just dates - it's responses in general. In the last six weeks, I've had a total of four qualified men email or wink at me (and by qualified, I do not mean they meet all my standard criteria - only that they're under the age of 40, and relatively nearby!).

So what gives? Are the men in Chicago just not as active in the online dating scene? Definitely a possibility, given that so many in this city seem to have moved here as a group with their college friends, limiting the necessity to expand their social circle (as opposed to DC, where everyone's looking for new partners-in-crime). But that can't be the only reason. If anything, there seem to be far more boys - particularly cute and gainfully employed ones - on the site in Chicago than there were out East.

Which leaves me to wonder what's the story? Is Match.com in this city a hoax? Is eHarmony the way to go (if you can get through that questionnaire, more power to you!)? Are the men here really aliens disgused to look like nice Midwesterners?

Please share your theories - I really want to know! And I'll keep you posted on any new clues I discover as I sleuth around the Windy City.

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:).

I've Got a Date!

Helloooooo Chicago!

I'm happy to report that dating prospects in the Windy City look good...VERY good. In fact, I was asked out less than 48 hours after moving to town. And, it happened in the cutest way. What more can a girl ask for?

Like any good law-abiding citizen, I headed to the DMV immediately after settling into my new apartment (ok, admittedly, I may have learned the hard way that it's far easier to deal with this stuff on the front end than to fix it later, but that's not the point).

And, like anyone that has a driver's license, I dreaded the visit to this office. In an attempt to limit the amount of time devoted to the less-than-pleasant experience, I hopped on the bus with my newly purchased CTA pass before 8am.

Unfortunately, it was raining. A lot. And I got lost. Thus, I spent twenty minutes wandering around downtown looking for the right building, well aware that my chances for a good driver's license picture were vanishing with every wrong turn.

Anyway, I eventually arrived at the DMV, bedraggled, but determined. I had done my research and had every document I could possibly need - and then some - to prove my new residency in Illinois. There was just one thing the multiple state, city and DMV websites failed to mention - they don't take Visa! Discover, Mastercard, Amex and check - all a-ok. But Visa, the most widely recognized credit card in the world, known for being accepted globally, is NOT a valid form of payment in th eyes of Chicago driving authorities.

Out I went back into the rain to track down two different ATMs before I could compile the necessary cash for the day's expensive transactions (seriously, $200 to transfer the title of my car!).

Finally, finally, I had everything I needed and all I had to do was wait for the office to open. Luckily, I was second in line. Thinking it might be a good idea to silence my cell phone to prevent any untimely interruptions, I pulled out my new Nokia and began to fiddle with it. Except, I could not for the life of me figure out how to put it on vibrate, or worse, turn it off. At this point, I turned to the guy next to me and laughingly explained my problem. With a grin, he was kind enough to help me out (I knew I had missed Midwesterners for a reason).

As we followed each other from station to station within the office, filling out the required paperwork, I eyed him up and down. My age, blond hair, runner's build, 5'11"ish and definitely cute.

Hmmm....this has possibilities, I thought. Granted, he was there to register his new moped, but since I didn't know anyone else in the city yet, it wasn't like I really had a ton of people knocking down my door to hang out.

And then it happened. In true Jerry Springer-style, proving perhaps every stereotype about government employees, the DMV erupted into a legitimate cat fight. Two of the clerks, at windows across the room from each other, began to scream back and forth about how neither knew how to do her job - and the rest of the employees took it in stride as though it was a regular occurrence!

While entertaining, this ridiculous situation also afforded me the opportunity to chat with DMV-boy. Turns out, he went to a neighboring high school in Minnesota! With great happiness, I concluded my business, but sadly turned to leave. I started to wave good bye, while wondering if I should ask him to get a cup of coffee, when he read my mind and asked ME if I wanted to go out sometime. The Chicago dating stars had aligned!

Even better, as he was getting my number, it was his turn in line, and he told the DMV clerk "Just a minute." The shock reverbrated around the room - someone was telling a state employee, a person who had the power to make his life miserable, just a minute?

"I'm trying to get a date here!" he said loudly.

Sigh. If this works out, it's going to be an adorable story for the grandkids.