Exploring Posts Tagged

Dating Stories

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]

Tagged As: , , , ,

Dating

You Saw Your Ex, Now What?

Published On: June 24th, 2011 by Single City Guy | 2 Comments

A woman, waiting for the N Train at 59th Street in NYC

Managing a post-relationship is a hard process. The way the breakup was handled with the ex, influences the reaction you’ll receive when you see them again. Trust me, you will see your ex again, especially when you least expect it.

Living in New York, you must be ready to meet any number of random people at any given time or situation. This includes the people from your previous relationships. In a sense, for me, the last few weeks were a series of extremes. On one hand, I was reaching out to a woman who I dated, got along bey well with, only to lose communication. In every way, romantically or not, I was making trying to interject myself into her life. Because things ended well, the conversation went well. On the other hand, I crossed paths with Rule Breaker on the train recently, and while things ended amicably, the reaction received was far from that. [Read The Rest Of This Entry]

Tagged As: , , ,

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]

Tagged As: , ,

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]

Tagged As: , ,

Dating

Effortlessly Approaching A Tall Woman

Published On: May 23rd, 2011 by Single City Guy | 1 Comment

A very tall, beautiful woman sitting on the floor

Last week, while out with dating coach Thomas Edwards, I told him, “You’ll be really proud of me. The way I handle women now, in public spaces is completely different from when you first met me.” What I didn’t realize at the time, was how much I was going to prove myself te accuracy of that statement. It was Friday evening, and I was out with friends at a new, trendy midtown bar. The night had been good to me: drinks were had, I flirted with their co-workers (who at this point had left), and was ready for the continued, evening adventures. As things were wrapping up, a tall women passed the group. “Damn, she’s really tall! I wonder how tall she is?” my friend asked me. Even though she was merely being inquisitive, it made me consider, finding the answer to the question. I was now determined to find out how tall she was.

This would require an approach. [Read The Rest Of This Entry]

Tagged As: , , ,

Dating

What Is She Going To Say, No?

Published On: April 13th, 2011 by Single City Guy | 7 Comments

A few weeks ago, I went out with a few fellow bloggers, who are also fans of Single City Guy. They mentioned a concern they had. They wondered about my lack of story telling, and were afraid I had lost the personal prospective about dating in the city. The truth is, this isn’t a journal, and every date doesn’t deserve a blog post. Some of the dates I go on, aren’t helpful for you, the reader. I’ve become selective with the stories I tell from my dating life, not due to any embarrassment or guilt, but due to the lessons gleaned from my experiences.

I make this point to say, this post is one I believe every guy should read. While it’s not a story of a date, but rather a situation that has led to a date, the reason i think it’s important, is because it addresses a situation every guy faces. Approaching a woman, while in public. One of the reasons men don’t approach women, is because we’re scared of rejection. If the only risk of asking an attractive women is by her saying “no”, isn’t it worth the risk?

[Read The Rest Of This Entry]

Tagged As: , , , ,

Dating

An Old School Approach: This Stuff Works!

Published On: December 21st, 2010 by Guest Author | 8 Comments

A Couple Ice Skating in Bryant Park

This guest post of some recent dating sucess was written by my dear friend, Kerri Kilbourne.

Rather than playing the “three strikes and you’re out” card, I’d like to turn the tables and highlight what one man did to make me say…”he did three things perfectly, and I want to get to know him.”

Last weekend, I went to a hockey game with one of the few friends I have in my new city. I met a bunch of “friends of friends”, and hit it off with the whole group. It seems though, that I sparked the interest of one person in particular. The man slipped a piece of paper with his name and number to a friend of mine & asked her to pass it along. Kind of 7th grade-ish, but…no harm, no foul. On that paper, he did crack a joke at the fact that I’d been calling him by the wrong name all day, which was charming, showing he has a good sense of humor. Cheer number one for him: proactively give me your number & put me in the driver’s seat. I liked that. [Read The Rest Of This Entry]

Tagged As: , , ,

Dating

The Best Laid Plans, Often Go Astray (#DateNightChallenge, Week 1)

Published On: October 19th, 2010 by Single City Guy | 1 Comment

Poor schedule planning

Dating after a breakup is quite awkward (and could be seen as offensive). I’m not the type of person to curl into a ball and mope around, I need to reach out and partake in my social life, even if it means trying to go on a date. I didn’t want to meet anyone new, I just wanted to enjoy some company with a friend. If anything, I was in NDD (non-date, date) territory, and an opportunity presented itself. A friend, who wanted to play catchup, was eager to see me and perhaps have a drink or two. Our plans, however, went astray. [Read The Rest Of This Entry]

Tagged As: , , ,

Dating

The Club Girl

Published On: June 15th, 2010 by Single City Guy | No Comments

I don’t remember when this happened, but I had finished reading The Game and was ready to put what I’ve learned into practice. I’ve been clubbing frequently, and figure it would be a perfect chance to see if what I’ve learned actually works. I often when with friends to Crobar, (now M2 Ultra Lounge). Often, my friends would end up with someone at the end of the night and I would be heading home alone. Tonight I hoped to change this trend.

I was nervous but confident. My uncertainty about my probably for success didn’t hinder my eagerness to try. Determined, I approached women throughout the night with a vigor I hadn’t had in the past. Some advances worked, others did not, but I was never undeterred to try again. In the end, I thought, it was all practice. However, in reality, I wanted to end up with a woman, naked. [Read The Rest Of This Entry]

Tagged As: , , ,

Dating

The Lawyer

Published On: May 16th, 2010 by Single City Guy | No Comments

The Supreme Court of the United States

I was going to hang out at my bar. The same bar where my adventures in alcohol had begun many years ago. I promised myself only a few drinks, make an attempt to meet someone new, and enjoy myself. Otherwise it was going to be another lonely Saturday night with my regular date, pints of beer.

I struck a conversation with other women who came to the bar. None of them were particularly special or was a person I had a particular interest. Somehow, I was on a roll this night, I’ve collected a number or two, but never understood what I did to grab their attention. I can’t quite remember what I did, but my confidence level was thru the roof. It wasn’t soon after I got my second number that she approached the bar for a drink. A glass of wine, it was red. I noticed her earlier in the evening when she entered with what I assumed was her boyfriend. [Read The Rest Of This Entry]

Tagged As: , ,

« Older Entries