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Good Dates

Dating

Meeting Her On The Subway

Published On: July 1st, 2011 by Single City Guy | 20 Comments

A woman walking down a subway tunnel to a train

A few months ago, I wrote about an experience of picking up a woman while on the train. I never talked about what happened afterwards, and if I was successful. Not to spoil the post, but my experience ends in frustration, although it was a very positive experience. Train Woman was cool, we had matching attitudes and sarcasm to bounce jokes off of each other, and remain playful, and flirtatious. Approaching her on the train, seemed to add to the playful, witty nature of our banter. It showed that I’m bold and decisive with my actions.

The first date went well, it started off as drinks, but turned into a dinner. Things were going so well, that it lasted for four hours, opposed to just one. This was a good sign, one that led to a second date. [Read The Rest Of This Entry]

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Dating

Opportunity Missed

Published On: June 20th, 2011 by Single City Guy | No Comments

A man, hunched over a chair in missed opporunity

Last week, I reminisced about a woman, who I had a series of great dates with, only to find myself interrupted by work. It’s a not so tragic story, but common in the New York dating life. The biggest kick in the pants was that the both of us got along quite well, only to walk away with nothing, not even a friendship is appalling.

It was suggested that I should reach out to her, with some of you using my own words against me. In a sense, it was crowd source dating. Before attempting to reestablish the lost connection, I had already figured she had forgotten about me and had moved on with her life. To my surprise, there was an exclamation mark at the end of my name as a response from the text I sent. [Read The Rest Of This Entry]

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Dating

When Poor Timing and Work Interrupts

Published On: June 14th, 2011 by Single City Guy | 4 Comments

 

A man looking at his laptop screen dumbfounded

At a recent speed dating event, I met an attractive, successful woman who I got along with quite well. She was a sports fan, looking for a long-term relationship, who had an eye for adventure. In many ways, we seemed like a great match. We had the same communication preferences, liked the same things, and in many ways were on similar, if not the same level. The differences we had were minimal, and easily to navigate. So why am I still single?

Success in dating often hinges on a key, but hidden cause, good timing. In this case between myself and this woman (dubbed Basketball Girl), my poor timing dashed any romantic hopes. It’s placed me in an awkward zone that I’ve yet to recover. [Read The Rest Of This Entry]

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Dating

Rule Breaker and The Third Date

Published On: March 8th, 2010 by Single City Guy | 2 Comments

A happy couple, on a drink date

The third date is a very important date. The last woman to make it to a third date was XPG, and things ended awkwardly. Rule Breaker had made it to this important part in the dating process and intuitively many decisions were going to be made. Due to the dates importance, the date itself had to carry some weight, we decided on an Italian place near her apartment. [Read The Rest Of This Entry]

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Dating

Working Without A Script

Published On: February 18th, 2010 by Single City Guy | 6 Comments

Walking towards the next chapter

Rule Breaker is a woman definitely have an interest in. After our first date, I wanted to see her again, and the plan was to see her a week after the first one. At this point, I didn’t know what I was doing. All of the dating advice, rules, and tips were being stacked in an order that I could not predict or was being thrown own. I was working without a script, a plan, most of it had been thrown out. After the first date, I had every intention to call her the next day. Things didn’t happen that easily.

I got dumped into a world insane schedules and work that would eat my time like Pac-Man would power pills. The day after our date, I didn’t call, neither the day after that, or the following day. I kept on arriving home late, being exhausted from the work I was doing, having to juggle a few million other things. This wasn’t a good thing at all. It wasn’t until Saturday when I dialed her number, but she was out of town and I was reacquainted with her best friend, her voicemail. [Read The Rest Of This Entry]

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Dating

Ignoring The Rules

Published On: February 15th, 2010 by Single City Guy | 5 Comments

Broken smiling mugI’ve previously mentioned the rules to dating are meant to be bent. When you meet a person you form a real connection with, often the rules aren’t bent, but broken regardless of the consequences. It’s never a one sided situation, either both people are breaking and bending the rules, or everything is following in their structured manner. I introduced Rule Breaker when I discussed the benefits of being persistent, but that’s not how she earned that nickname, our first date sealed the deal.

“Breaking the rules” means so many different things. First it’s the stereotypical male/female roles that we’re supposed to play while dating. While, in this situation, most of these were rules were maintained, she did break some of them. For instance, she was the one who asked for my number, how many women do this? The second type of rules that were broken are the things you’re supposed to do while dating someone, things to say, not to say, topics that should be addressed on the first date, etc. It was her upfront, honest personality that made me comfortable, as I’m an honest, upfront person. This set of rule breaks I had learned from talking to her on the phone. [Read The Rest Of This Entry]

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Dating

Persistence Gets The Date

Published On: February 5th, 2010 by Single City Guy | 2 Comments

A motivational message on persistence

The old adage, “If you want it, you’ll fight for it,” holds a lot of weight in terms of dating. However, finding the right date involves more than just fighting, it involves being persistent, vigilant, and responsive.  I experienced this truth thru attempting to meet a recent OkCupid responder. This woman, I’m dubbing, “Rule Breaker”. The story of Rule Breaker has many parts, this is the prologue, but more importantly, it’s a demonstration of a powerful dating lesson. Be persistent. Not overbearing, persistent. [Read The Rest Of This Entry]

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Dating

I Scored a Right Angle

Published On: January 11th, 2010 by Single City Guy | 6 Comments

A skee ball on the lane

It’s hard to go out with someone when they know my true identity. It’s hard to maintain my anonymity, especially when really great women approach the barrier I’ve created. The usually manage to maintain my secret, but some women get thru. Skee Woman is one of these women. I met her through my many social media connects and we decided to go out. We really didn’t know each other, but there was enough of an interest that it would be an interesting time.

[Read The Rest Of This Entry]

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Dating

Speed Dating with 30-Somethings

Published On: December 22nd, 2009 by Single City Guy | 2 Comments

The number, Thirty-three

Last week, I went to another unique speed dating event. It was an over 30 event where single 30-somethings searched for other single 30-somethings. I’m 28, not only the youngest in the room but not a 30-something either. Amber, from OnSpeedDating.com, invited me to this event (in part to the poorly attended Cougar Night) and reassured me that I would fit in with the crowd. Unlike the other events, I was surrounded by a group where I clearly did not fit in.

I’m reminded of a talk I had with Thomas Edwards about this very same subject. Many times I find myself as the odd-piece in a crowd of people. Either I’m the only minority in the room, or one of the youngest in the room. I’ve always seen this as a liability. Thomas made me see the glass half-full and use it as an advantage. I was unique, and my unique qualities would separate me from the other in the room. In essence, I was a unicorn. As a unicorn, I embraced my unique quality. I was younger than everyone in the room. I had to pair this with a lesson I was learning, presentation and how it was key. [Read The Rest Of This Entry]

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Dating

Cougar Speed Dating

Published On: December 16th, 2009 by Single City Guy | No Comments

Photo of a cougar, ready to pounce

The mental image I had of a cougar wasn’t favorable at all. The phrase has such a vague meaning and negative connotation. I did a google search to ease my nerves and found a picture of the recently crowned Miss Cougar California. If the women at this event were going to look anything like her, it wouldn’t be so bad. Lets remember two things before I continue, first I live in New York City, second I live in New York City. NYC has beautiful, gorgeous women of all ages, they do maintain themselves very well. This city has some of the most gorgeous women ever. In actuality the cougars at the event were more like Stacy’s Mom or Stifler’s mom.

I’m not really fond of the term Cougar. While I’ve always been attracted to older women (as in women older than my current age), Cougar seems wrong. For the purposes of this post, we’re going to call them “older women.” [Read The Rest Of This Entry]

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