All the Single Ladies

Went on another Matchy-Match last night - and going into it, I KNEW this guy and I were not going to be compatible, but I thought - eh - free drinks, fancy hotel bar, and who knows - a good story.

The Prep:

So “Winky the Third” as he will be called from here on out (although he more resembles the aesthetic of Mr. Scott Disick) actually winked at me on Match almost a month ago.  I didn’t reply to said wink until Monday when I thought - eh - why the hell not.  He wrote me back quickly and asked if I wanted to meet him for a drink on Thursday or Friday this week.  WOW - fast!  I was intrigued. 

I of course said only Thursday would work because I of course have plans on a Friday night (even if it is just Bridesmaids with 2 A & C).  We were meeting at 9 at this hotel bar on 57th and Lex - and I of course was running about 10-15 min late - but I got my nails did, my hair curled, had a fun new dress AND put on red lipstick!  I looked cute (at least before I went subterranean on the subway system)

The Drinks Date:

Strike one - He came up and said hi and went for a hug - which I blocked and stuck in my hand for a nice shake. We found a nice seat for two and were going to have our date of drinks.  I order a Vodka Soda - he orders…….. a PEPSI.  He doesn’t drink!!!!! 

He asked a lot of questions in his very preppy and NYC rich boy accent (which surprisingly made me want to giggle more than be disgusted).  He was very completementary and engaging.  I was getting comfortable, and then bam:  I learned these facts that just kept getting better and better because I couldn’t believe they were real:

(1) He works in finance

(2) He gets to work at 430 AM every morning

(3) He doesn’t like to drink and is NOT a social person.  He actually used the term “social pariah” to describe himself

(4) He grew up in the tri-state area his whole life - and has never really travelled outside of his comfort zone

(5) He went to boarding school in Connecticut

(6) He was an All American SQUASH player (What???) and he wanted to go pro, but his stupid parents made him go to a fancy prep school that didn’t have a good squash program.  Wah!

(7) He went to Harvard (where he found acceptable Squash partners)

(8) He wears shirts with cufflinks and dresses UBER-preppy

(9) He’s never had a roommate and lives in his own apt on the UES

(10) He is NOT okay with me having close guy friends as he doesn’t believe in platonic male-female relationships.  He’s super jealous and said it drives him insane.

(11) He doesn’t take vacations - he wants to retire early and just have enough money to do whatever he wants - like own private jets and houses all over the world and just play squash all the time

(12) He never goes below 42nd street and he doesn’t take public transporation

(13) He is a country club member in Westchester

At the end of the date I told him that we were completely opposite people in every way.  I think he perceives me as a flighty, kumbaya hippie girl and I see him as a polite version of Scott Disick.  We would actually work in any circumstance - but he wanted to hang out with me again - Sunday to be exact - movie and pizza at his place.

I was hesitant (and still think he may not actually follow through with this) but after talking to my BFF last night, I’ve decided I’m going to label this my Pretty Woman Project.  He’s the Richard Gere to my Julia Roberts.  I’m just what he needs to put some fun and relaxation into his life and he’s going to teach me to be a responsible adult and maybe let me quit my job of prostituing my soul to the corporate world and support me to go to culinary school and be a lady who lunches. 

I will keep you posted on progress of Project Pretty Woman - if my Winky the Third calls me back.