Ashley York Vol 1: Beginning

As I alluded to the other day, this will be the beginning of the end. Super dramatic, I know. The following series of posts will recount a tale from back in 2008. Please note that this isn’t based on a true story. This is a true story. Sometimes I may change a name or ad lib a dialogue, but this is actually how it all went down. There’s no embellishing here. I want you to remember this as you read on. No embellishing. I’ve been sitting on this for two years now, and I’m happy to be getting down in writing and sharing it with you. I hope you’ll enjoy.

It was about 90 degrees already at 8am, which for Aruba isn’t particularly unusual. As I did most mornings of this vacation, I woke up incredibly early and went down to the beach to claim a little hut and beach chairs that would prevent us from dying of heat stroke and alcohol poisoning in the blistering midday sun. With me on this vacation were three friends from Michigan. Fuller, Old Greg, and Hutchybear. The trip is exactly what you’d expect from four guys in paradise. A lot of drinking, a lot of throwing around the football in the water, and a lot of hitting on girls, almost always unsuccessfully. In fact, it was actually kind of funny to “throw salt” on each other’s game by interrupting innocent flirting by saying “oh, so I see you’ve met my friend Joran Van Der Sloot”. Sorry. Too soon?

After coming back upstairs to the room that morning, stepping over empties, making a PB&J, and putting on Lil Wayne’s “Lollipop” for the four hundredth time, I opened up the computer my friend had brought and decided to check my email and of course Facebook. Since I was the only one without a blackberry at that point I was feeling slightly disconnected, and relished the opportunity to catch up while the boys were still passed out. I grabbed a seat by the kitchen counter and logged in. It almost seemed wrong connecting back to the world. I could hear the birds, and the ocean, and the curtains flicked against the wall with the gentle Aruban breeze. The thought of starting my summer internship in a little more than a week made me literally cringe. Talk about a tough transition.

Now to be perfectly honest here, I’d been dating a girl from school, kinda, and she had just graduated. She happened to have been an undergrad. Whatever. We had hung out back in New York before the trip and while I had absolutely no desire or aspirations of dating her, I thought at least I would’ve seen an email from her in my inbox. Nothing. A touch dismayed, I then opened up Facebook to a message and friend request from a very cute blonde girl named Krista Marks.

The name did not ring a bell and I tend to always remember a name and almost always a face. Her note read something to the effect of “Hey, I don’t know if you remember me, but we met in the Hamptons last summer. I just wanted to say hello and tell you I think you’d be a really great match for my friend”.

Tom Stoppard once said, “every exit is an entrance somewhere”. This was awfully convenient considering nothing was doing with this Michigan girl. I’m not going to lie. I was kind of intrigued by Krista. If Krista’s friend looked anything like Krista then I was about to meet a very pretty girl. But still, I had no idea who Krista Marks was. At this point the guys began to stir, the first beer was cracked open, and it was not time for computers. I accepted Krista’s friend request and wrote the following:

“Krista, I have to apologize, but I can’t quite remember where we met. Where exactly were we?”

We kicked ass that day out on the beach. Fuller, as always, represented America with his portable NASCAR beer cooler/satchel and doled out ice-cold Balashi’s all day to the four of us. We even befriended two girls, one of which was stunning. Her last name was Van Peenen and she had recently received breast implants. Isn’t it weird the details you remember? Anyway, by day’s end the four of us and our two new friends had turned one of these thatched beach umbrella hut things into a regular bar. As we all hung out, listened to music, and had a good time I couldn’t help but think about this Krista Marks character. Perhaps not 100% sober at this point I placed our meeting at Stephen Talkhouse in the summer of 2007. I wanted to believe I’d met her. Hell, maybe I did.

After we all deemed it essential to passing out in the room before dinner I checked the computer again, and lo and behold, a response from my new friend Krista.

“I forget the name of the bar we met at. Whatever. I think you’d really be great for my friend Ashley. What do you think?”

Well at this point we were Facebook friends because she had accepted my request, so I got to look at her profile. Old Westbury, New York. Puzzling. Not to stereotype, but I didn’t realize they made them tall and blond in that part of Long Island. She seemed sporty. Lots of Lilly Pulitzer. Very pretty friends. What did I have to lose?

I wrote, “Hey. I’m up for a set up. I’m actually going to be back in the city this summer, so I’d be willing to meet your friend Ashley”.

Krista’s response, not five minutes later, “Great. Her name is Ashley York. If she found out I was trying to set her up she’d kill me. She doesn’t like setups but I really think it would be a good match. Just send her a message and don’t mention me. Be cute and funny”.

Me writing back to Krista, “I’ll give it a try, but she has no clue who I am. This is kind of ridiculous. I’m a complete stranger. There’s no way it’s going to work”. But then I went onto Ashley York’s facebook profile and I was actually shocked. This girl was a straight up knockout. She had stunning blue eyes, although I’ve seen MUCH better since, and looked like a model. A little bit hungry looking, which I don’t particularly care for, but hot nonetheless. So I mustered up the courage, and wrote a short but sweet email to Ashley York. It read something like

“Hi Ashley. We haven’t met, but we have a bunch of mutual friends in common. I came across your profile and just thought I’d drop you a note. I’m actually back in the city this summer and thought it might a fun to grab a drink if you were available. I know this is really out of the blue, but it’s always nice to meet some new people. Hope you are enjoying the summer”.

Now, that is me trying to remember what I wrote two years ago. Clearly it wasn’t that, but that’s what I think I would’ve written. Total cheeseball awkwardness. I’m taking a little bit of artistic license here. But you write a note to a total stranger model and tell me what you’d say.

The next day I woke up early and hopped on the computer and was excited to see a note from Ashley York. It read “New York is a lot of fun. Enjoy being back”. Well, not exactly what I was looking for. I wrote back to Krista thanking her for trying to make it happen, but told her that it makes no sense why a complete stranger would want to meet me, and how if she just set us up herself, which I still couldn’t understand why she wouldn’t, then we might have a chance of actually meeting. Later that day Krista got back to me and urged me to try again and be funnier and more charming. I liked this Krista Marks. I didn’t know her, but I liked her. Lots of “LOL” and exclamation points, but her enthusiasm was appreciated. It was nice to have her in my corner trying to make this happen.

Unfortunately though, I was taking off. We’d managed to escape Aruba while not getting arrested or deported. My Aruba vacation and Ashley York will forever be entwined. I was off to a wedding in Toronto though. Krista’s unbridled enthusiasm and Ashley’s apparent surliness would have to wait until after I got back from the wedding.

Next: Making contact, cucumber sandwiches, and the Royal Ascot.