"Update" NYC


As 2011 is coming to a close I was quite excited to have one more date to get under my belt with hopes that maybe, just maybe, this final date of 2011 would turn into fireworks, chemistry and so much electricity that the entire city of New York would have yet another blackout from all heat we would be generating.

We would be that couple sitting at the table that the other singletons give glares at.

We would be that couple that would be so excited talking to each other that we end up actually talking over each other.

We would be that couple that upon first glance you would think that we have been together for years.

We met on match.com. He is a copywriter; we even known some of the same people in the industry and the email exchanges were witty with just a smidge of flirtation. Given the holidays and schedules it took us two weeks to even pick a date on when to meet.  Seeing that we knew some of the same people, I could have contacted these friends of ours and asked what he was like but I decided that I don’t want anyone’s opinions but my own to determine if this was the right guy for me or not.

This guy played his cards very well with me with moments that were leading up to the actual date. He emailed, he sent text messages and get this…he even talked to me on the phone for an hour where we found out we have even more in common than just a few mutual friends.  Nowadays with texting, Facebook, Twitter and all these social medias it is rare to even have a phone conversation with a potential date. It felt foreign at first to talk with a guy on the phone but oddly enough it is just like riding a bike. Once I started I couldn’t shut the hell up. I knew I had to wind the conversation down for I was going into the territory of revealing too much too soon. So I chose the ever so popular excuse of, “it is getting late and I have to work tomorrow”, so we ended the conversation by saying goodnight and we will keep in touch. I thought for sure since we had chemistry over this phone conversation that he would ask me out but all I received was the dial tone.

It wasn’t until the next day after the phone conversation that I got the email from him saying how much fun he thinks I am and that if I were interested he would like to take me out to dinner on Tuesday. I got the email and immediately got excited but instead of responding right away, I distracted myself with work and responded a full hour later to say “Sure. Sounds great. Let me know the details”.  I am not sure about others out there but I come from the dating school where if someone asks you out that it is that person’s responsibility to pick the place, time, etc. Nothing pisses me off more when it comes to dating when someone asks you out and than the person says, “So, what do you wanna do”. It reeks of laziness and to me that is usually Strike 1 for the person.

Much to my surprise, in his response to my email he not only picked the time but the restaurant. I already liked his phone manners and from the photos I saw I was somewhat attracted to him.  So now the true test was coming, the test of chemistry once you meet the person face to face. First dates, as we all know, can be nerve racking, uncomfortable at times or down right awful. But for every one of those horrific dates, you do find those rare treasures of the great first date. At times, I often wonder if the Perfect Date is a mere urban myth but I certainly didn’t mind doing the research to see if the Perfect Date actually does exist.

It is now Tuesday, the night of the date. I leave work on time, rush to the gym for that quick workout and while on the treadmill doing a mental run through of everything in my closet to figure out what to wear that night. You don’t want to over dress but you don’t want to look like a slob either. So I opted for semi-casual, dark jeans, boots, button down shirt (tucked in), belt, coat and a scarf I just purchased for the occasion.

Onto the streets of the city I go. As I walked the few blocks from my apartment to the restaurant I said a little prayer to the Dating Gods that he is not a freak, he looks like his photos and he doesn’t leave me in the middle of the date with the bill (yes it happened to me once).  As I am in route, I am running a few minutes behind and I get a text from him saying he is waiting at the bar. I walk in and there he is, sitting at the bar playing with his iPhone and he is the only one at the bar so I am not too worried about coming up to a stranger and it not being him.

Not sure how this happened but he didn’t exactly look like his photos. It wasn’t that his photos were taken 1998 but rather his photos made him seem adventurous, funny and charismatic. The minute he saw me he just said “Wow. Nice.” I told him “Thank you. I think.” I wasn’t sure what he meant by his comment and I didn’t want to dig deeper; at least not yet anyway.

As we are seated in this South African restaurant where the entire place is decorated in bamboo sticks, I noticed that he had done some shopping at Bed, Bath and Beyond before meeting me. So I asked him what he bought at the store and in the driest tone he proceeded to tell me all about his purchases…It was there that I knew I was going to need some wine on this date to liven things up a bit.

The waitress approached our table and I have this rule, especially on first dates. And that is, I usually let the guy order his drink first. That way, if he just sticks with water or a soda; I am not the person that orders the alcohol first and they think that I am a functioning alcoholic.  So I was really hoping that he was going to either suggest we order a bottle of wine or that we get some mixed cocktails. Turns out…he doesn’t care to drink all that much and he is sticking with tap water. I tell the waitress I will be sticking with the same as him and that is where I begin to try and get to know this man.

As I mentioned earlier about his dry tone as he was explaining his purchases, I first thought the tone was because his purchases were actually quite boring but it turns out that is not the items that were boring but it was him.  His tone never changed, he was simply and utterly a snooze fest. I knew right than and there what I had to do and that was to work my ass off by asking questions about his life and even trying to create different topics to chat about seeing we covered a lot over topics over the phone earlier in the week.

Usually your average conversation with another human being consists of you asking a question, the other person answering that question and than the other person will ask you a question back. This particular guy had not picked up on the basic etiquette of conversation. So for every single question I asked him, he would answer and than that is where the conversation stopped. He never asked me a question and he didn’t even seem that interested.

It dawned on me that I was on a date with, Interview Guy. Interview Guy, is that guy that I have been on a date with a few times in my dating career. This is the guy that will sit and wait for me to ask all the questions and never once asks me question back in return. I am doing all the heavy lifting and he is just sitting back and enjoying the ride.

After a torturous conversation about what we are ordering dinner; I decided that I might as well make the most of this situation and try and get to know him a bit better. Every single time I asked him a question his was response was either “We already discussed that over the phone” or he would answer the questions and say “Next topic.” I felt like I working for the CIA and I was trying to get information out of someone that was being put under interrogation.

Finally the food arrived and we could just sit in silence and eat fast.  Half way through the meal a miracle had occurred and he asked me a question first. He asked if he could try a bite of my meal. Usually I don’t mind when people ask, I don’t mind sharing at all. But this guy was annoying me for being so damn boring that I said I wasn’t comfortable with him eating off my plate. He looked at me as if I was the rudest person on earth but I no longer cared. I was sitting at a dinner table sleeping with my eyes open.

He suggested we get dessert but I shot a quick response back with how full I was from the meal and that I should get going. He motioned the waitress for the check and just as the check arrived at the table he proceeded to say to me “I think we need to go half on this meal.” I certainly didn’t mind doing so but how he addressed it really put me off.  So once again, we sat in silence as the waitress processed our credit cards and came back with the receipts.

As we grabbed our coats and made our way to the restaurant I begin to do a quick observation of the other patrons at the establishment and I was just a smidge jealous for there were tables of people on dates laughing having a good time and I was about to go home with another dud of a date. We got to the street and much to my surprise the date said how much fun he had and that we should do it again. I don’t know what my face looked like but it definitely was a face that told him we are NEVER doing this again. I wished him well and happy holidays and he went one way and I went another.

Turns out, the last date for 2011 wasn’t the best, it certainly wasn’t the worse either. Now it is time to focus on what matters for the remaining days of this year. And that is Friends, Family, Laughter, Reflection and Hope.

This is my last entry for 2011 and I just want to thank you all for your support, for reading, for sharing and for even commenting. I wish you all Happy & Healthy Holidays and to get ready because 2012 is the year of endless possibilities…this is “Up”Date NYC after all!





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