Chase (v): To follow rapidly in order to catch (this could pertain to my career), to go and follow in pursuit (I think I’ll assign this to love)

I wish I had a PhD in life, unfortunately I don’t. It’s a hard thing to do and being an independent woman in Boston doesn’t make it any easier; I’m a triple A, work till I drop, laugh a lot because I can, walk fast, talk fast kinda girl. I do it all and I do it in 5 inch heels.

You would think navigating a career and a new relationship while breaking the age barrier of 30 would be as easy as getting home in a timely manner during a sox-yankees series (this ladies and gents is sarcasm at its finest). However it is not and I am stumbling through this cray cray life one day at a time with a iPhone in one hand and a glass of wine in the other.

These are my daily musings; my everyday observations. I am here to rave, rant , tell my stories and perhaps laugh at those times when wine and over priced shoes, tears just aren’t enough.

So what happens after you caught Prince Charming? You could say I’m still Chasing Boston.

Monday, October 4, 2010

Episode 8: “The Urban Legend of Dating

We have all heard the stories, THE story to be exact, the one that makes single girls shutter with horror. I have been fortunate enough to never experience it, or know anyone first hand who has, however that all changed one dreary evening in Boston, let me set the stage;

Mr. Pretty Face approached me one night out on the town someplace between glass 4 of champagne and my first pickle back shot (if you don’t know what that is….Google it). I was teetering on my ridiculously high heels, and he happened to be standing next to me when I accidently flung my phone into his lap. After what I have been told was a good 20 minute conversation, he asked for my number. Since I was punch drunk off of his dimples that wouldn’t quit I happily obliged (did I mention that I actually gave him my card, and said, “Here’s where to look if you want to find me” Keepin it Classy.)

Like any normal human, now that he had my info he sure did find me, right on Facebook and when I got a random message from a ridiculously good looking man, I was SHOCKED to find out it was him asking for a date. Not that I can’t get a model looking dude, but come on…..something didn’t click, or had I overnight, perfected my game?? Hmmm.

We met at a trendy little resto in the South End and to my surprise he was even better looking in person then I remember and as we sat at our table in the corner and chatted away, it all started to make perfect sense. The conversation was about a 5 as he was talking on and on about his fraternity (basically at this point we are at a full count 3-2) and then he said “Yeah, I mean, me and my frat brothers would listen to lenny Kravitz I belong to you and just dance around, you know like on a Friday night….

STRIKE ONE! This would classify as “Things to never say to a female that you are trying to impress” I figured I would let this slide given it was a first offense.

We finished dinner and decided that we should head over to the Charlesmark Hotel, both on our way home and to partake in one more bevy before calling it quits. As the bartender approached us, I placed my order and then Mr. Pretty Face placed his:

“I’ll I have a Key Lime Martini….oh but wait, can you make sure that there is a graham cracker crust rim and that you also put just a dollop of whip cream on the top…Pretty Please!” He Then turns to me and says “I love this place, they always play the best techno”

STRRRRRIIIIKE TWO! The bartender glances at me; I back at him and decide to change my order to a patron on the rocks. We have officially crossed into Tequila Territory, and there is no way I am leaving this establishment sober. Mr. PF excuses himself to go to the bathroom and Bartender comes over “Soooo is he?” “I don’t know!?!?! You think?” “There is only one way to find out….”

And as Mr. Pretty Face came back to his seat he said “OMG, you have to see the treatment to the walls in the bathroom, AH.MAZ.ING, it reminds me of the shoes you were wearing the night we met” The Bartender, at this point pipes up and says: “and there it is” then proceeds to pour me a shot of Tequila.

STRRRRIIIIIKE 3, you’re out! Literally you are OUT, I am officially hauling you out of your “straight” pants and putting you in full body leather and glitter where you belong!

My name is Courtney, I have gone on a date with a gay man…..and survived…with the help of prescription meds and one damn good therapist.


  1. I used to work for Spruce and John passed your blog along for me to read. I started a blog about my dating life about two years ago. I also write about all the ridiculous things that happen to us that sound almost too ridiculous to be real! I feel your dating pain! Good luck!

  2. HA! Great story! And really good blog! Randomly stumbled on you through Twitter somehow. I'll be following.

    I have a dating blog I randomly update as crazy dates happen: Enjoy!

  3. Thanks guys!!! seriously can you believe what the dating world is like?? thank god for friends and wine!!!