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Some people just seem to have it all. A comfy job, their health and wealth, and a sweet honey to come home to on these freezing Chicago winter nights. And to those who fall into that category, I say congrats! You've got it made! But for all of you who stumble in to your studio apartment from a night of cat-and-mouse at some Wrigleyville bar, to find the only sweetie waiting for you is a pint of Half Baked, I say "This blog is for you!" And me. And all brave Chicagoans who are committed to dating.

Whether you're an occasional bar hopper or a serial dater, I'm here for you. I will explore, observe, and date the heck out of our fine city. This blog will give you a shoulder to cry on, a friend to confide in, even a pillow to punch (though we take no responsibility for your broken MacBook). Or, at the very least, an insightful look into the local dating experience. Sure, if you're single and in Chicago, dating can be painful, frustrating and seemingly hopeless. I understand, and I'm here for you. No, this blog does not guarantee to cure your ailing love life, but if you let it, it might open your eyes to a city-full of possibilities.About the author.

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Welcome

About this blog

Some people just seem to have it all. A comfy job, their health and wealth, and a sweet honey to come home to on these freezing Chicago winter nights. And to those who fall into that category, I say congrats! You've got it made! But for all of you who stumble in to your studio apartment from a night of cat-and-mouse at some Wrigleyville bar, to find the only sweetie waiting for you is a pint of Half Baked, I say "This blog is for you!" And me. And all brave Chicagoans who are committed to dating.

Whether you're an occasional bar hopper or a serial dater, I'm here for you. I will explore, observe, and date the heck out of our fine city. This blog will give you a shoulder to cry on, a friend to confide in, even a pillow to punch (though we take no responsibility for your broken MacBook). Or, at the very least, an insightful look into the local dating experience. Sure, if you're single and in Chicago, dating can be painful, frustrating and seemingly hopeless. I understand, and I'm here for you. No, this blog does not guarantee to cure your ailing love life, but if you let it, it might open your eyes to a city-full of possibilities.About the author.

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Baby, It's Getting Cold Outside

Stop! Put down your cell phone and don't even think about that
casual Facebook message. I know what you're thinking, because I was in
the same boat. The minute I finally
got into the habit of regularly shaving my legs, pre-winter comes
straight out of nowehere and blows right up my skirt. And seeing this
here is Chicago, there is a very good chance the blizzard of '08 will
veto my slutty lobster Halloween costume and I'll be stuck resurrecting
the not-so-slutty unicorn onesie of '92. With wet socks and cold noses
in the not-so-distant future, any self-preserving Chicagoan defaults to
the winter survival tactic second only to those hideous-but-glorious Ugg boots.

A fellow human being. The hibernation instinct overcomes any common
sense, and when the thermostat dips below 50 we find ourselves running
into the arms of the nearest source of body heat. And there's nothing
wrong with that. But combine that particular unbridled urge with my
laziness for going out and meeting anyone new, and I find myself bored,
hiding under the covers and simultaneously scrolling through my recent
contacts and recent memories for that lucky fellah who deserves a second chance at love, with me. (Think Rock of Love 2 without the cat fights)

Seems like a fine idea, right? God knows we all made our summer
mistakes, or just held on too tight to the hope of running into
Christian Bale while he was in town filming Public Enemies, and didn't
want to be tied down in case we did. And now that reality has set in,
and Christian Bale has moved on (sob), it seems like there's no harm in
back-pedaling just a little bit to see if that nice guy who seemed into
it is, in fact, just what the doctor ordered!

Well, ladies and gentleman, do whatever you need to. These are
desperate times (blog on not shacking up with I-Bankers to come). But
let me relay to you a little recap of my recent revisiting experience
to give you some perspective.

Just last week, I found myself shocked awake by a cool breeze
blowing through my wide-open window. Burrowing under my thin blanket
and hugging my ice-cold knees to my chest, I ran through the options in
my head. Buy a down comforter, OR— light a little flame under, well, a past
flame! I mentally ticked through my hookups in the past year. After
ruling out the psychos, the geographically remote, and the guys who had dumped me
(I have some dignity, really) my ticker tape of a love life landed on
Josh. Perfect! Only 6 months since I last saw him, and I bet we could
pick up right where we left off. He was so nice! Intelligent, funny,
equally sporadic work schedule, making him the obvious companion for wintertime weekday mornings like this one! It wasn't his
fault that he liked me at a time in my life when I was only into guys
who didn't like me. What was I thinking breaking it off with him!? Girl, you crazy, I'm thinking to myself, as I flip open my laptop, find him on gchat, and dive right in:

Me: Hey!
Him: Hey…
Me: [small talk]
Him: [small talk]

Pause
Me: so are you seeing anyone?
Him: I am
Me: bugger!
Him: lol, why?
Me: I was going to ask you out!
Him: oh. well, believe it or not, I'm engaged.
Me: haha you're a dirty liar
Him: I'm serious…
Me: …I'm going to go talk to the wall.

Me: oh… and, um…congrats…

jflksjhhlaskjdghs!! Suddenly determined to stay hidden under my thin
blanket forever, that little exchange jolted me back into reality.
Maybe I wasn't so remiss to end that particular relationship. He and I
were simply not in the same place in our lives. While marriage would
certainly provide a [constant] companion by the fireplace, that's not my cup of hot
chocolate for this particular winter. And if you're reading this, Josh,
I wish you all the happiness in the world for all seasons to come. As
for me, I'm going to go unpack my Uggs and trudge on.

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Speed Dating

There’s something to be said for Love at First Sight. We’ve seen it work in the movies, heard about it from the ideal couple, and daydreamed about it happening any minute now. And as mythical as any smart, cynical dater knows this pipe dream to be, it remains lodged at the peak of our Mt Everest of romance, shamelessly holding the #1 spot in our Top 10 How We Met wishlist.

Oh, how silly. Everyone knows we’re going to end up with that nice guy who has been picking up the slack all these years, biding his time until we come around and realize that HE’s what it’s all about. Fine. I can handle that fate. But until then… A girl can dream, can’t she?

Well sure she can, but it’s not always a good idea. If you’re me, you’ll do it anyway and then have fabulous stories to tell you all. So here we go: Refusing to heed the cynics and my own good sense, I stepped into the dating world on this dream alone. And to what results…

Step One: Sight. According to my research, as love at first sight promises, you’ll see The One, he or she will see you, and BAM you’ll just KNOW. I figured that didn’t seem impossible. He only need be insanely attractive to grab my sight. And sans girlfriend (details, I tell you). So I started looking on all corners. A few grabbed my eye, a few passed me by, and I was near defeat when one day the gods stopped working for Tyra and decided to pay a little attention. They planted him across the street from the theater I worked at in a mop of curly blond hair and a barista apron. Perfecto Espresso! I was over there every night before the show, fixing to fix my fate with “Coffee Guy”. Fortunately, this particular theatrical endeavor of mine had me workin’ some fishnets and a lot of red lipstick, and like Grandma always told me, that’s the easiest way to get a man. Sure enough, sight-for-sight had us exchanging numbers and making plans for a night out.

Not long after he called to confirm, I started exhibiting irrational love-struck behaviors. I was scrawling out Mrs. Christine {His Last Name} on every bar napkin before I even knew his last name. What did I have to worry about? This was my newfound fate! I had found love at first sight with the Coffee Guy! A much more cynical friend with a few years on my lime green self commended me with her usual sarcastic flair on my ability to fall in love with someone I know absolutely nothing about. I told her that was the point, duh, as I joyfully mused on our retirement cottage in Nova Scotia. I had achieved the impossible! The hard part was over! Only a lovely downhill slope from here, kids.

Or spiral, depending how you look at it. Well the first date found me drinking whiskey and soda on an empty stomach, and that coupled with my blind enthusiasm had me gleefully dropping the “Like” word and (I think) agreeing to be his girlfriend. Date # 2 took us to 80s night at Neo, which was just a little bit insane. As it turns out, he loves to dance by himself in a style that can only be categorized as Tecktonik meets The Twist, leaving me feebly shimmying the night away in an effort to keep up. (Oh I tried dancing with, but he said couples dancing messed up his rhythm, and sure enough, he fell over when I tried anyway) Whatever, I figured, so 80s music is his thing. This was just one of those personality traits I couldn’t read based on sight alone. And wasn’t this blind love affair what I had signed up for? Swallowing fast the creeping doubt, I charged right up to Date #3.

A quiet Sunday night at Danny’s Tavern (no 80s music, per my request) started with a detour at his apartment, for a “gift” he had picked up for me (his girlfriend.) That’s when the panic set in. Gift? How does he know what I like!? Does he even know what my favorite color is? Come to think of it, our first date breezed right past that vital conversation! Oh God, what if this gift is something Taupe?! Well, readers, this gift was…

… Shiny black pleather pants. That's right. Some sort of shiny, black, synthetic material shaped into PANTS. Now it’s weird to get pants as a gift from anyone, unless they are of the neon sweat variety and from your kooky aunt. And it may be weirder to get them on such short notice (a mere three dates in, remember) and from someone who barely knows you (though, oddly enough, guessed your pants size to a T) So there I stood in all that shiny glory, thoroughly weirded out, and it dawned on me that I have gotten myself into something entirely different from what I thought I was getting myself into. What happened to that adorable guy who was supposed to be my soulmate? Surely there’s been some mix-up! And I’m sure he was standing there, witnessing the look on my face, and thinking, “What happened to that girl who was supposed to love these shiny pants?” Both of us stood guilty of falling “in love” with the wrong person.

I supposed that’s what I get for impulse-buying a relationship; the clouded perception of what it is I’ve gotten myself into, followed quickly by the buyer's regret of something that wasn’t quite what I had in mind. As for the guy, I can’t fault him, even with his relative lack of sense regarding ladies fashion. How was he to know that I had fallen in love with the sight of him; a mere idea up against his true character—who I am sure some girl much less square with an equal passion for 80s music will love and adore. As for me, maybe I’ll think twice before fussing with my fate in the future. In the meantime, if anyone has an idea of what top would go with these pants...

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The Fling's the Thing?

Oh, look, it's mid-July, and summer is in full swing. Chicago’s street festivals have outdone themselves yet again, the beach has delivered a few rousing games of volleyball and my winter-white complexion is finally surrendering to the sun. Snow season is a million light-years away, and summer has been, overall, worth the wait.

Except for that one thing that seems to have eluded me during this fair-weathered stint: the summer fling. Winter delivered the cozy video-game-prone boyfriend of a light-less basement apartment and an aversion to venturing outside (fine by me), and spring bounced back with a young, hip dilettante with a regular party schedule and an obscure Itunes library. Enter, summer. With its wealth of outdoor activities, short shorts and beer gardens, I was promised a slew of eligible young gentlemen, primed for a fling. (noun: a 3-month, casual encounter with unspoken codes of conduct set in place by summer romances past, full of al fresco dining, hot summer nights and a tragic but necessary parting come sweater-season.) Well, a few unpromising encounters and an all-too-eager suitor later (call me come February) leaves me with nothing short of seasonal affective disorder. Until one day…

I meet "M." (cue trumpets) M was at a mutual friend’s dinner party, and we hit it off right away. Numbers were exchanged, plans tossed around, and wham bam thank you ma’am we were Facebooking. Before I knew it, I was blowing off Mr. Come-To-My-Sister’s-Wedding and skipping a heartbeat when I heard the beep-beep-beep of my text message notification (or whenever someone unlocks an SUV. It’s really too cruel; I should change my ring tone.) Finally a DATE was set. We were to meet at M’s place for drinks, head to an art show and then to a friend’s birthday soiree. A perfect summer night. Roommate Dennis and I agonized over outfits (too “dressy” to too “messy“ to too “Karen Allen circa Raiders of the Lost Ark”) until I had concocted the perfect summer ensemble. Running late, I booked it to the Clark bus, breathlessly ran up M’s steps, overzealously rang the bell and gave my smartest smile as…

She answered the door. That’s right. “M" is a girl. Ha! I knew it all along, but I had you going for a while, huh? Yup, wearing a stylish dress (that I could totally borrow) with a vodka tonic in hand, I knew I had found my summer fling. We shared our respective travel adventures, career aspirations and of course, boy dramas, over many a cocktail before we headed out to start the night. A cross-town bus ride, an art show and a 7-11 slurpee later, I found myself in a well-lit alley with M and some of my friends who had come to meet us and share in the blissful summer night.

As we sat around, loudly laughing and passing around the pomegranate-green apple slurpee (yes, the flavor of summer), I couldn’t believe I had it this good. Who needs a fair-weather fling when I’ve found an all-weather friend? Let’s admit it, flings seem like a good idea in the throes of humidity, but after the ice cream has melted and the sniffles set in, what we once fell for in our idealistic fling can fade just as fast as those summer tans.

Instead, with my new friend and some tried-and-true old ones, in a city that was made for its summers, I finally feel seasonally satisfied, and for all seasons! But let’s wait a little bit longer for that sweater. This is too good to fling away.

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Models Shmodels

You can’t write this s#*$. Let’s try anyway. Girl meets boy. Boy seems awesome. Girl Likes boy. Things going well… until. Boy tells girl he is seeing another girl, too. Girl is semi-crushed, but picks herself up and agrees to taking things easy. Dum diddly dee Girl is totally cool UNTIL. Girl runs into Boy with Other Girl and, while face is maintained in the moment, Girl gives in to darkest urges and Googles Other Girl to find…..

… Out that she’s a model. Nude. Lingerie. Did I say nude? Yes, nude. Crud.

Oh, Readers. This Girl is so unfortunately, me. And I’m not telling you this for your sympathy, or affirmations, or even your offerings of bourbon and ice cream. To tell you the truth, I’ve already had the bourbon and ice cream, and I’m in need of some distraction; so to you I write. Dating is hard, as we know, and as your dating blogger I feel like I should share with you the bad experiences as well as the good. So humor me by letting me humor you, because I’m being left for a totally naked blonde. (Oh, your sympathy? No, I simply couldn’t. Ohhh allright, if you insist)

OK, enough of this pity-party. I think this could be a dating lesson for all of us. Maybe my experience can guide you with what to do in case this happens to you— and you are not the model. Because let’s face it, if you’re reading this at a desk that is void of a strategically placed high powered fan over a lunch that consists of more than cigarettes, you are not The Model. But they exist, and date the same guys as you and me.

As they deserve to! Lest we forget, models are people too. And I’m not about to hate on a girl just because she happened upon the genes for freakish height and far- set eyes. But how the hell do you compete with A Model?!

You can’t, really. Because boys will be boys, and models will be models, and boys like legs and it’s as simple as that. Buuuut you can certainly put up a fight. Because there are certain things that non-models have that are just as natural as God-given cheekbones. Years of dating as a non-model equips a “normal girl” with skills and strategies for attracting a guy beyond knowing her angles. Years of practicing eye contact, bar-sidling, clever comebacks, charming anecdotes etc, vault us into a confident, sexy stratosphere that should make any model quake in her stillettos! Sure they have the walk, but we have the talk. You want the score of the game? Which one?. Politics? Please, I spent my Friday night watching Washington Week in Review. Hey— check out these sick dance moves! Did I tell you I make a mean risotto? It goes on and on. 

And Voila. Before you know it you’re right “up there” with the model, in a figurative sense that avoids the danger of grazing the ceiling fan. And that ability to hold your own will catch a few eyes! And the guy that sees right past a pair of pouty lips and straight to your asymmetrical eyebrows might be the keeper indeed. So party on, non-models. Let’s strut our stuff.

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Date My Dress

The saying goes something like, “Don’t judge a book by its cover," and I’d like to say that I adhere to age-old adages as much as the next guy. Lately, however, I’ve been struggling with this one in particular when it comes to my dating life. I’ve noticed recently that guys and girls alike are falling victim to my critical eye, getting the once-over and being mentally tossed into the “yes” or “no” pile based on a couple of snap judgments. Now I know a good bicep when I see one, and would love to date his bone structure at all costs, but this time, my radar isn’t even reaching skin-deep.

I’m talking about personal style, from the neckerchief to the floor. And my particular indiscretion, while superficial in context, is far from superficially motivated. Thanks to today’s fashion trends, SO much more can be read about a person just by looking at what he or she is wearing. With the advent of the “hipster” and the “trixie” or whatever overly descriptive, mildly constricting genre one happens to fall into, everything from music taste to favorite cocktail can be read on what you pull out of your closet. No longer do I feel guilty for snap judging! Simple self-expression has morphed into blatant advertising of the minutest personal details. Tight black T-shirt, skinny jeans and Converse = Joy Division and a PBR, while a strappy halter with a white jean skirt couldn’t be more Maroon Five with a Bacardi & Diet. Over-sized t-shirt, cargo shorts and Vans? Nirvana me up with a MGD on tap.

Now you can understand my panic, when I’m on to Date #3 and I’ve already rolled out the neutral and casual comfy T-shirt for Date #1 and the fail-safe, sex-on-eggs dress for Date #2, leaving me with some cash tips and raw shopping nerve to splurge on the quintessential outfit that will reveal all the right things about me.

So off I go, to the Chicago shopper's mecca: Michigan Ave and then some. The Loehman’s, the Nordstrom’s, the Macy’s, the H&M etc. Gasping and clawing, I bravely fight my way through the hordes of tweens on their prom-dress hunt, suburbanites on the pre-Wicked matinee time clock and corporate honeys dieting away their lunch break. Despite a (relatively) full wallet and a (relatively) open-mind, I somehow come up empty-handed.

To be utterly dramatic, nothing captured “me!" It seemed impossible to get away from the seasonal jewel-tones that sent visions of Jolly Ranchers dancing in my head, or the idiotic pockets on shapeless cotton dress and those infamous gladiator sandals. Forget about revealing too much cleavage. I’m worried about revealing a false identity! What? You think I’m high maintenance and only eat dry toast?! No, no! It’s only my strappy sandals before noon talking!!

Sigh. Yet fear not, for I eventually found something to wear. Exhausted and near defeat, I met up with my dearest friend Dennis and stumbled into a vintage store on the way home. And as far away as possible from current (and even recent) trends… I found my outfit. (And Dennis found his).

Judge away, but try and pinpoint a predictable mode of behavior with this blinding gradient leotard and red boater flats! Ok, maybe it’s a little predictable or reminiscent of my participation in the 1988 Summer Olympics as a member of the Lithuanian gymnastics team, but at least it’s fantastically fun (and not to mention, ridiculous...ly comfortable)

Or maybe it is just as revealing of my personality— in its own, funny way. Who knows what details about my life can be read on its electric blue exterior, but its mere existence on my person works as a bit of honest advertising at the very least. Yes, I AM fun, and a little crazy, and actually do have the balls to wear this thing out in public. And what guy doesn’t like a little confidence with his spandex? We’ll just have to see… Wish me luck, daters. I’ll let you know how it goes.

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