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!

The New Love of My Life

That’s right, I’m in LOVE…the dreamy, toe-tingling, can’t get enough of you, never wanting to let you go, cuddle all night, absolutely trusting kind of love…with my BED!

Ok, so maybe it’s not perfect – at only 3 ft. high it’s a bit vertically challenged, and at 5 ft. wide it has trouble fitting through doors for a night on the town – but it never disappoints. Each morning as I reluctantly leave the comfort of my soft, organic cotton, 325-thread count sheets, I begin to count the hours until I can sink back into the unique pillow-top design of my Westin Heavenly mattress. And when the day ends and I can finally pull my luxurious comforter up over my shoulders, a feeling of absolute bliss washes over me.

My faith in my bed is unshakeable – I KNOW it will always be there for me (and after paying to ship it from DC, it better be!). As I snuggle in to its comforting embrace, I feel safe, secured and loved – what you’re SUPPOSED to experience in a committed relationship, right?

Sure, it’s not all rainbows and butterflies, and like any relationship, compromises do have to be made. For instance, spooning can be a bit more difficult, but we get by just fine with some extra pillows and the help of my teddy bear. And as I mentioned, I’m still stuck having dinner alone – but how is that so different than with a boyfriend that regularly works late.

All in all, seems like a pretty satisfying pairing to me. But, not to worry – I haven’t gone completely bonkers and given up dating or anything. In fact, I’ve got dates lined up with two different men next week!

Oh My God, I Love Your Accent, Where Are You From?

That was the tagline on the profile of my one and only Match.com date in the last six weeks.

Intriguing, though, to be sure. Further investigation revealed this gentleman to be 28, educated, solidly employed (with a salary of $75,001-$100,000 no less, although I do not understand why some people actually list that) and a lack of kids (lets face it, this is NOT a given anymore!).

Another bonus: The guy can write and clearly has a sense of humor, as his "recent passions include creating iPhone applications, mastering my Spaghetti Bolognese recipe, completing 100 push ups in a row and jumping from wake to wake while wake-boarding."

But the most exciting thing - you didn't forget that accent, did you? - He's from Ireland! Which, admittedly, was a lot more exciting until I thought to check a map and remembered that Ireland, unfortunately, is NOT part of the UK. Why does this matter? Because I desperately want to move to London, and as a kindly alum from the University of Missouri recently pointed out in response to a query for advice, my best hope of doing this is to marry a Brit.

So, convinced this was going to be my future husband (I hadn't checked the map yet), I happily agreed to meet him for a drink.

We initially agreed on Rockit Bar, which immediately had me questioning my future husband's choice of hang-outs. Although I've never been there, for some reason I have this picture in my head of it as a d-bag magnet, so my excitement was mildly dimmed over by the idea that this was his go-to first date spot.

Luckily, he texted a couple of hours before we were to meet and suggested a change of venue to McCormick & Schmicks - things were looking up! Granted, this brought up concerns (which turned out to be very real) that he'd want to do dinner instead of just drinks, and I always prefer to stick with just a beverage on the first night, but on the flip side I figured he must have re-thought just how excited he was to meet me.

I happily walked the short distance from work to the restaurant, convinced this would be a match made in heaven that I would be recounting years later for our kids and grandkids.

SCREEEEEEEECHHHHHHHHHHHHHHHHHH!!!! Or so the daydream in my head went the moment I met Ireland boy. I should have known that anyone whos posts only a single picture with their profile, and one that's truly a "profile pic" at that, isn't very likely to make me weak at the knees. "But looks aren't everything," I firmly told myself. And it's true - I really do think a person gets more attractive the more you get to know them.

But then he opened his mouth - and sadly, while a very pleasant person, we just did NOT click. To make things worse, as we were making awkward small talk about what to order (he clearly had no idea how expensive the restaurant was and quickly settled on a bowl of soup!), I had a sudden flashback of a near perfect date at the same restaurant (read about it here).

Needless to say, my hopes of being married and living in London this time next year have been squashed. Oh, well. There's always the company exchange program!

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:).