Do I learn from previous mistakes?

One is often posed with the question of whether something was a mistake to learn from...
OR if the particular situation, people involved, and timing made the outcome least optimal.

Last Saturday night was an exceptionally busy one that required planning ahead and strategy.

Party 1: Hedge Fund Guys - Surprise B-day Party for a coworker of the PM (coach in The Boob Crusher post) at a Meatpacking District venue.

Party 2: More Hedge Fund Guys - Gigantic Apartment B-day Party of the Jet Setter's friend - who my friend Gold Digger is currently interested in.

Party 3: Finance & Marketing Guys - Artsy Loft Party for a coworker friend of the aforementioned Gold Digger.

Party 4: Questionable Guys (didn't make it so I'm not sure) - B-day Party for the Aspiring Actress' new J-boyfriend's friend at an Awful Venue in Midtown.

Reasons we needed to go to each and every party:

• An adorable, tall, laid back, and smart foreign coworker of PM (that I made out with & have a crush on) was expected to be at Party 1.
• It was about time that I met the Jet Setter and he very well could have some good friends for me to date at Party 2.
• Party 3 was one that we could go to first, arrive early (before 11:30 PM), and start getting our buzz on.
• Finally, this very tall Jewish guy that I had a slumber party with a few weeks ago could have been at Party 4 and it would have been nice to get the awkward and inevitable running into each other thing out of the way.

Guess what...
I met a guy at the first party we went to - Party 3.

He's tall, older, and dresses well, but he was shy (insecure?)

I could tell he wanted to approach me BUT after his 5th failed attempt of getting the courage, I decided to take matters into my own hands, while my gal pals were having a smoke.

After all, this first encounter would undoubtedly set the precedent man-eater mood for the parties we would attend later on in the evening.

There I was, making something up about juice that I couldn't find and it worked. All he needed was an "in" (a hint that this girl will actually talk to him).

We took up to chatting a bit and then I cut things short when my buddies returned from the cigarette break.

When we were leaving this soiree for Party 1, I said my goodbyes and that's when this gentleman tried to persuade me to stay.

It wasn't happening.... and he just didn't get it! So annoying.

I had to ask him if he wanted my phone number!!! What a disappointment!

Obviously he took it and called me the very same night, but I was already at one of the other functions and so I didn't answer.

It's been a week & I haven't heard from him again.

Should I throw this guy into the same bucket as the Boob Crusher and learn from my mistake?

Are some shy guys okay to date OR are they all insecure with good reason?

If you were wondering - Party 1 was a bummer as the Foreigner didn't show and it was so late by the time we made it to Party 2, that it was pretty much faded out.

The Troll (Another Dreaded Parental Hook-Up)

My father had mentioned that a business associate of his had a son around my age that was single. He gave my father his e-mail address. My father, possibly with previous incident, knew better than to hand out my contact information.

When he told me what little he knew about the guy - all positive of course, I figured - what did I have to lose by e-mailing him. With the new leaf that I've turned recently, in being the one to approach the man, I thought this would be good practice AND if he turned out to be an okay guy - great!

The e-mail I sent from work on a Friday (after consulting with Cut & Dry, an online dating friend of mine, as I'm only a novice at writing an introductory letter), included an okay picture of me and I asked him to send one of himself as well.

Not to sound conceited, but I am quite photogenic most of the time. In fact, sometimes when I see pictures of myself it's hard to believe I can look that good in real life. However, I really sent an average looking picture to this guy.

He immediately responded to my e-mail but I was very busy at work to reply back. By Monday, he had written a second e-mail and attached a picture.

It was atrocious!
He looked like a troll without the hair (receding hairline, big ears, pointy nose, squinty eyes)!

You can imagine that I was not anxious to write back but I finally did a few days later. Keeping it very brief and staying polite. At this point, I was afraid to lead him on any further.

Again, his response came within the hour. Then another e-mail later in the day and another the next day. I hadn't responded to three e-mails before he started asking for my number!!!

This may sound superficial, but I just couldn't give this guy a chance.

Having to come up with the CLOSING letter, I consulted many friends. They offered lots of advice, but finally I settled on some lie about getting serious with a guy that I have been casually dating.

He wrote back!

If your parents are trying to set you up with a guy that they haven't seen and don't have a picture of, don't date him New York!

If a normal looking guy approaches you while you're walking down the street with your friend and says "I would fuck the shit out of you", don't date him NY!

The Boob Crusher (3rd Date Investment)

One night I was out on the town with my male friend (The PM) which already makes the odds of meeting another guy pretty slim hence we went to my favorite place for men - PS450.

We were drinking at the bar and scoping out the people, commenting on appearances and behavior of the young professional crowd. It's pretty amusing to observe really.

That's when I saw a good-looking, well-dressed, 6'3 (my ideal), shy guy standing alone while his friend hit on some girl with bad taste in shoes.

Some time later and half-way into my Very Berry Mojito, PM urged me to approach the bored-looking boy. This is something I don't know much about since they usually come to me and wow does that take courage! PM told me what to say - nothing complex or anything but I was glad that I didn't have to think of anything nonetheless.

We hit it off and exchanged phone numbers. He seemed interested when he called and we immediately set up a date for later on in the week - a good sign from the start.

I think I've turned a new leaf when it comes to being the pursuer... I kind of like it!

After two dates with lots of talking and no physical contact (no kissing - nothing), I knew we had to step it up on date # 3. This guy was a catch - Tall, Good Family, Sound Job, Compatible Religious Background, Solid Private School Education in a Ritzy Community, and we had hours of conversation without a hint of the normal dating interview question & answer session.

I consulted with PM about our dates and he asked me a question that I never thought of before - did you offer to pay? I didn't and I don't think I ever have. I was always told not to and even my male friends have paid for me.

After a major discussion, we decided to survey some people we know on the topic. To my surprise, the majority of people we asked think that the woman should offer to pay even if it's insincere. It's like a test... if he let's the female pay, never date him again! Personally, I don't get it. Why ask a question that you don't want the answer to? But that's another story.

There I am on my way to my 3rd date and in my mind the tests are coming. We went, we talked, I offered, and he actually accepted!!!

I was shocked... but I had to see if there was any physical connection after I panned out the dough (hold on - was I turning into the man in this?)

Finally we went to his place and kissed. It was terrible. Not the kiss itself but everything else. His apartment smelled like B.O. and mildew. He grabbed my boobs so hard that they hurt the next day and everywhere that he touched me felt like probing.

I actually got out of the clasp by claiming that I needed to use the bathroom and giving some lame excuse when I got out. "It's getting late. I think I should go now."

So, if you're at a bar and you see a good-looking guy standing alone, there's probably a great reason for his lack of confidence. Don't date him New York.

The Gypsy Artist (better known as Barcelona)

Let me preface by giving the reason that I'm starting with Barcelona... In a nut shell, he is the only one that I thought I ever loved. When you're done reading this post, I'm sure you'll have doubts of these feelings and maybe even come to your own conclusions about why I am SINGLE!

See Barcelona was a friend of a friend of a friend, which is one of the best ways to meet a guy in this corrupt city - isn't it??? When I speak to happy couples, the most common story they share of meeting is through a friend. Admittingly when a friend introduces me to someone, it almost gives the guy validation... he automatically has one step above any other random guy.
So what if there was a few extensions to my story? It's not like I met him at a bar/club (like the many others).

It was early (before 2:00 PM) on a weekend day when my roommates and I went for brunch at 7A (one of my favorites) dressed in a regular brunch outfit (not-really- trying- to- impress- but- just- in- case- I- run- into- anyone- I- know- on- the- way look). About 3/4s of the way through brunch I realized (with help of a text of "where are we meeting") that I had actually made plans (an uncommon occurrence) with some other friends (The Candid Colorist & Brooklyn) to see an art exhibit on the other side of town (the West side).

There was no time to finish the meal AND go back home to change.

I was off to the art exhibit with the wrong outfit and even worse the wrong hair!!!

Candid had a friend in town from CA and was going to meet him and some friends at an apartment afterwards so me and Brooklyn came along.

Barcelona opened the door and as soon as I saw him there was something there. But the day turned into evening and we didn't have any incredible one-on-one conversation yet.

The group of us ate dinner together and then went for Margaritas & Spanish music at this awful Mexican spot that I really like. Barcelona & I couldn't have sat more far apart from each other if we had tried to... it was looking hopeless.
But when I have my mind set to something or someone, they don't really have a chance... my Margaritas were settling in and the dancing was about to unite us once and for all. We were the only two in our group to hit the floor and the others were ready to leave.

When we all got outside, Brooklyn & I were the only ones heading to the East but Barcelona insisted on walking with us. The dear friend that she is, Brooklyn asked questions that I never would have and then nonchalantly hopped into a cab to head back into the borough.

Finally, we were alone.

It was the most spectacular night and you could actually see stars in the New York City sky. We walked and talked for hours, passing my apartment and walked along the East River walkway. He held my hand, he complimented me in ways that others couldn't fathom, and when he finally kissed me it was like he was in love with me and like we've known each other forever.

I know what you must be thinking but it wasn't all empty conversation about how great I am... that was just bonus.

Among phylosophical conversation, our deep thoughts on life, and the people in it, I learned that this night was his last in town. He had lived in New Jersey, Barcelona, Minnesota, and New York as an artist and the next night he was going back to Barcelona where he would continue to paint.

It was all so romantic and although I can't say that I'm "that type," I was on this perfect night.

For days after meeting him my head was in the clouds and I told everyone that I was in love. When I say everyone it includes my mother, my father, my grandparents, my manicure lady, my bikini wax lady, my coworkers, my friends, a stylist that blow dried my hair, and a few people in between.

Finally, I could try to understand that adage - better to have loved and lost than never to have loved at all. I was happy that I met him even if we wouldn't be together again in the immediate future.

Figuring the time it would take him to settle in, while taking into account my impatience, it took me a week to write a light email to Barcelona - just to give him my contact information and something to let him know that I wanted to stay in touch (without saying it).
What was I thinking? a romance in a foreign country perhaps? a reason to rediscover a place that I spent some good & bad times? I just had to do it.

Now here is the part that you've been waiting for... his response. It went along the lines of "it was great meeting you but now I'm here in Barcelona. Take care."

Oh yes - TAKE CARE!!!!!!!!!!!!!!!!!!!!!!!
He might as well have said F U... it would have been better that TAKE CARE.

So here I am left questioning whether it was really love that I felt, whether I would have loved him if he was an artist that was actually staying in NY, and whether I could feel love at all.

If you meet a guy that's leaving town tomorrow and says "take care," don't date him New York!

"and the City"

In a generation of online dating services - whether it be Match, J-date,
E-harmony, and so on, some of us are still hesitant to sign up.

We're the ones who think that meeting someone in real life first (then they can start sending text messages, IMs, & e-mails - but that's another story) is possible.

It's "the story" we're after - the tale that our grandchildren will hear about... our good old days.

So you can only imagine all the different ways we meet these characters!

Quite often my girls and I will sit around (with cocktails in hand) and give the report of how awful (or rarely how great) our latest date was and that's when it hit us... we should write about this!

These stories are too incredible to make up yet they're so unbelievable.

The great thing about my dynamic group of gal pals is that they are not all about having "the story" like I am (some are online dating, some don't think they will have grandchildren, and some just can't tell a story). We all have different ways that we meet guys - through friends, through work, at bars, in the diner, the dreaded parental set-ups. We are attracted to various qualities and we each have unique standards (I guess that's how we CAN stay friends).

In this blog, we will share with you the intricacies of our encounters on the dating scene in NYC. Think "Sex and the City" without so much sex... so I guess its just "and the City".

So welcome and stay tuned for stories like The Gypsy Artist, The Boob Crusher, The Troll, and The F'ed Up Fireman.