A Year in My Dating Life: A Look Back

Only recently did I realize that I've had this blog for a little over a year now. It's been a year since I started sharing my thoughts with the world, a year since I moved back to downtown Chicago, a year since I weaned myself off daily doses of delicious dinners (courtesy of the mom), and most importantly - it's been a year since I rejoined the dating world after a long hiatus.

When I lived at home in the burbs and my roommates consisted of mom and dad, my love life kind of took a nose dive. My socializing was done at work, and the weekends were spent in a literal drunken haze with my friends from college. I was still weaning myself off of my college party schedule, and therefore spent most Saturdays and Sundays hungover, curled up in a whimpering pathetic ball of human fail. Even if I met a normal, cute, smart, cultured, and decent member of the male species during that time I wouldn't have known what to do with myself. Basically, I was a hot mess.

When I finally had an apartment to call my own, I resolved myself to the notion of "acting more like an adult" while "eating frozen dinners only on days of the week that end in 'y'" and "putting myself out there". It was time for me to date again.

So I invite you to take a look back with me on my life in dating* from last year to present times. It wasn't always easy, it wasn't always fun, but like a champ I stuck with the program. I was determined to put myself out there, no matter how much the dudes sucked, were more metrosexual than the cast of Queer Eye, were rich and snobby, were borderline stalkers, or just plain old boring.

So, here we go. A look back....

1) Brandon

Lowdown: 28 year old attorney living in a tricked out condo in the heart of Chicago's posh Gold Coast neighborhood.

The Look: Resembles a European model. Expensive leather shoes, custom-made Armani suit, Cartier watch, silky locks that you just want to run your hands through.

First Date: Drinks at a posh bar in an upscale hotel- the epitome of glitz and glamour, where you can schmooze and rub elbows with Chicago's elite. Think clean, elegant lines, imported leather furniture, snooty cocktail waitresses, and drink ingredients that you can't even pronounce.

Oh #&$! Moment: When I asked what he and his friends like to do for fun, Brandon took a sip of his Manhattan and calmly exuded uppity-high class snippery, while he commented that he and his friends smoke cigars and drink in one of the main bars at The Drake Hotel on the weekends. This particular bar has a freaking HARP in it, people. So that's how he occupies his free time, you know, when he's not in New York or Miami.

What do I do for fun Brandon? I go to dive bars, take one too many shots, forget my name, and on occasion fall asleep in my stilettos. Glad you asked, but I must say thank you ever so much for the classy kiss goodnight.

Total Number of Dates: 1

Fail Scale: 7

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2) Will

Lowdown: Slightly rotund, slightly insane uber rich 26 year old who hails from a snooty, wealthy town in New England. Seemed visibly put out when he found out I drove a Honda Civic. Claimed to be a field agent for the government (rolls eyes).

The Look: Popped collar, designer label, casual frat attack look. The icing on the cake was the pair of beat up Sketchers he was wearing.

First Date: He took me to his favorite local bar for a drink or two. Kind of boring, but hey, it sufficed.

Oh (*#& Moment: When he immediately went into a tirade about the last 3 girls he took out and how he was confused as to why they never returned his phone calls. Ever. At this point I'm staring at the exit as beads of sweat begin to bead on my forehead.

Oh @)($ Moment #2: When the bill came, he did the "slow reach for his wallet" thing and seemed visibly put out when I held my gaze and didn't reach for my purse. After perusing our bill, he plopped the receipt down and half sighed as he signed his name and included a tip. The total was $20, and yes, I'm sure he wanted me to see the grand total. T-A-C-K-Y.

Oh (*#@ Moment #3: As I'm practically running to get away from him, he comments on the blizzard swirling around us and asks if he can bum a ride home, despite the fact that a bus could have picked him up outside the bar, and despite the fact that he lived 5 BLOCKS AWAY. Are you kidding me?

Oh *@&#! Moment #4: As I drove him home he made a quip about work and then casually mentioned my then company's name- despite the fact that I NEVER TOLD HIM the name. Holy. crap. Government man doing background checks on me?! He then tried to stick his tongue down my throat. WOOF.

Total Number of Dates: 1

Fail Scale: Definite 10

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3) The Enigma

Lowdown: 26 year old pretty boy from the suburbs, and kind of a male diva. DJs at downtown Chicago clubs, plays semi-pro football, is captain of a paintball team, never could admit when he was wrong, never could stop talking about himself, trained in the Navy Seals, and had one of the shortest fuses out of anyone I've ever met.

The Look: Metrosexual to the extreme, with a very "L.A." look. Always wore designer clothing, and no less than 5 pieces of jewelry at all times. Pretty sure he got his eyebrows done, and if a piece of hair was out of place he would flip out and become moody. He had more pieces of real designer clothes and accessories than I could ever hope to acquire in a lifetime. Let's just say that when his cats decided to use his $2,000 pair of Dolce shoes as a scratching post, I had to hear about it. For hours.

First Date: Drinks at the Signature Room Lounge at the top of the John Hancock building in Chicago. He paid, and acted like a gentleman. He scored big points during the beginning of our courtship- $300 dinners, taught me all about sushi, took me to movies, made me delicious home cooked meals, took me to meet all of his best friends, had me come watch him DJ, etc. It was during this time that I tried to push aside the fact that, well, he was just too METRO for me.

Oh @!*@ Moment: The time he called me at work, borderline hysterical and in a literal rage. He happened to look down while typing in his cubicle and realized that he was wearing a pair of OLIVE GREEN pants and not the GRAY ones that he had wanted to wear that day. The gray pants, Kayleigh, perfectly matched the colors in his tie and perfectly complimented his shoes. And guess what? His day was now RUINED.

Oh #*@! Moment #2: Whenever he had a bad day, he would call me at 5 pm and say, "UGH I had such a shit ass day. I'm going shopping, call you later." Wait, let's rewind the game tape. What? Isn't that MY job? Aren't you supposed to go home, grunt, and watch manly things on TV while guzzling beer when you have a bad day? Come on, sweetie, let me wear the dress in this relationship.

Oh *&#$ Moment #3: He had a credit card to the Juicy Couture store. I would rather set myself on fire and not shower for a week than wear something from that store, let alone set foot in it.

Oh @#$! Moment #4: We were out at a fancy Brazilian steakhouse for an elegant downtown dinner, while the subject of crazy things that happen to people in real life involving horrific accidents, and how people survive them came up. Why we were talking about such macabre things at a refined restaurant is beyond me- we talked on average of 4-6 hours a day so I guess weird stuff is bound to crop up. ANYWAY so my idiot self delves into this intricate and horrifying medical story that I think I read about in the newspaper.

After my 10 minute tirade, The Enigma calmly took a dainty bite of his pork tenderloin, a large sip of wine and commented with a deadpan expression: "Kayleigh...that was the plot of an episode of Grey's Anatomy."

As my face flushed crimson in embarrassment and with realization that hey, wow, he's right and gee, isn't this embarrassing, and um, can I possibly hide behind that giant rack of ribs, another part of me went: "Wait, hang on. Are you really schooling me on Grey's Anatomy episodes?!?"

Total Number of Dates: 15+

Fail Scale: 5

Why the middle of the road 5, you say? Let's just say I ignored his many faults because the man was gorgeous.

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4) Danny

Lowdown: 24 years old, big hot shot from the biggest insurance carrier in the U.S., traveled to places like India, Bangladesh, Ireland, and Japan for work, started his own multimillion dollar charity, collects wine, was his high school quarterback and owns his own home.

The Look: Everyday average looking guy, Italian, tall, with dark hair. Seemed like a man's man and someone who really knew how to relax.

First Date: Dinner at an outdoor cafe where we watched a fireworks show, and then went onto my roof top deck for chit chat and what he perceived would be cuddle time. FALSE.

Oh &@#! Moment: When he asked what my favorite movies were, I responded with "Terminator 2, Blues Brothers, Anchorman, and Nightmare Before Christmas." His response?

Monsters Inc., Finding Nemo, Toy Story, Supertroopers. In that order.

AWKWARD.

Oh !(@* Moment #2: When he took me to a comedy show and got lost THREE TIMES despite me saying "turn left here". He then decided to turn right. Or go straight. Or just do the opposite of what I said. I wanted to barrel roll out of the car into oncoming traffic.

Oh &@#! Moment #3: When in a desperate attempt to make conversation with me (since I was bored out of my mind staring at the ceiling, the floor, the cobwebs, and the doorway) he began asking me repeat questions of things we already had talked about for an hour. I did what any bored, and seemingly trapped female would have done: called him out on it.

Oh &#$@ Moment #4: As he dropped me off after date #2, he commented at how my street was empty. As he began to parallel park his PURPLE SCION, I icily proclaimed that my street was crowded and that it was a shame there weren't any more spaces. He got the message.

Total Number of Dates: 2

Fail Scale: 8

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So what did I learn from this past year in dating? It seems that I've dated some really rich, annoying, metrosexual, hot, rude, and boring dudes.

Here's to hoping this next year is better, and that the Fail Scale eventually hits below the "5" mark.

*Disclaimer: A date refers to going out to dinner, a movie, etc. with someone of the opposite sex, with the full understanding that it was indeed a date. This post does not refer to all the other encounters with men within the past year that were the result of drunken shenanigans, sexual tension, or bad decisions.