Dating
Published On: March 24th, 2010 by Single City Guy | 2 Comments

We all have our moments where we question our dating successes and failures. They are usually just that, a series of events that lead to some success or failure. While my dating life, overall, is a mixture of successes and failures, during my the periods where women weren’t responding to me, I began to ask, “what’s wrong with me?” By asking this question, I was ignoring the successes I’ve had, the lessons learned to build upon. Maybe the real answer to the question has nothing to do with me, but with women.
We all pass up opportunities, especially when it comes to dating. I’m not going to suggest that every woman I’ve dated has missed out on their best opportunity by by not seeking a relationship with me. That would be egotistical. I would be ignoring the flaws I have and would suggest that I’m the best choice for every woman in the world. It’s not the truth. There is a possibility that I’m not the best fit for the women I’ve dated in the past.
However, I do believe that women are often seeking cookie cutter men, instead of men right for them. There is a difference. [Read The Rest Of This Entry]
Tagged As: Dating Frustrations, Gripes, Personal Details
Dating
Published On: March 12th, 2010 by Single City Guy | 6 Comments
It’s been roughly seven weeks since I’ve first met Rule Breaker, a bit longer since our first communicate. About two weeks ago, after a trip from Cleveland, I decided to take myself off of the market and cave to my feelings. I asked her to become my girlfriend, and she said yes!
A friend once told me, you’ll know to start something exclusive with a woman when you don’t care to see any other women. While dating, I went on two dates with other women; but in my mind these were clearly of the non-date date variety. These two women I had met thru friends and social circles, were attractive, but I didn’t have want or inclination to move beyond potential new friends. [Read The Rest Of This Entry]
Tagged As: Girlfriend, Personal Details, Rule Breaker
Dating
Published On: January 26th, 2010 by Single City Guy | 12 Comments

“To be frank with you, I’m ridiculously surprised that your response rate has been so low. Your cute, your profile is good…,” was the first few lines of Laurie’s response concerning my lack of success with OkCupid. Even with the increased message count, I wasn’t receiving many responses. I feel I’ve become the ultimate dating enigma.
I like OkCupid, but maybe the population on the website isn’t geared for me. Laurie suggested that I switch over to Plenty of Fish, or as I like to call it Plenty of Fail! I’m not a fan of their dating website, it’s horribly put together, ugly, and not ad deep as OkCupid. However my lack of major success on the website leaves me little alternatives. [Read The Rest Of This Entry]
Tagged As: Dating Frustrations, Gripes, Personal Details
Single Life
Published On: December 25th, 2009 by Single City Guy | 2 Comments
Before reading this post, please make sure you’ve opened your presents, had some breakfast and spent some Christmas joy with the family. This post isn’t specifically a dating post, it’s a personal story that’s a bit sad. I’m NOT looking for any sympathy points with this story, in general I try to avoid these sorts of posts that aren’t related to dating. This time I felt the need to share this with you, my reader.
When people say they hate Christmas, I always wonder with befuddlement as to the reasons why? I never buy into the excuses for their bah-humbug attitude. While I hate the winter, I love Christmas. It’s one of the most festive, reflective and wonderful times of the year. There’s so many special things about Christmas that doesn’t happen during other times of the year, time spent with the family (even if you hate their guts), presents being opened, the joy spread across family members and loved ones. Whether the holiday is manufactured, it’s a gracious time of the year. One of the few. [Read The Rest Of This Entry]
Tagged As: Holidays, Personal Details, Stories
Dating
Published On: November 21st, 2009 by Single City Guy | 1 Comment
After a month of undergoing the eFlirtExpert program, you would think I would be dating the hell off my keyboard. While I’ve had a lot of success, I shared some of my thoughts with her and got a reminder that i’m contributing to the problem. The reminder was more like a kick in the ass. I’m repeating several of the same mistakes, but also creating brand new ones. [Read The Rest Of This Entry]
Tagged As: Dating Frustrations, Dating Mistakes, Personal Details, Personality vs Looks
Single Life
Published On: November 17th, 2009 by Single City Guy | 4 Comments

In the New Oxford American Dictionary, the term polyamory is defined as “the philosophy or state of being in love or romantically involved with more than one person at the same time.” To be in a polyamorous relationship means you have multiple lovers, but what about multiple loves? For almost two years I’ve been in a relationship with 3 other women, who are all across the country. All of them are single, two of them are in monogamous relationships, and all of them I consider loves. These women are very important to me, as we are emotionally invested into one another. They are more than friends, but short of benefits, and all very important to my life. They are so embedded into my inner circle, it feels as if we are in a polyamorous relationship. [Read The Rest Of This Entry]
Tagged As: Personal Details, Polyamorous, Relationships
Single Life
Published On: October 23rd, 2009 by Single City Guy | 2 Comments
Single City Guy was an idea rattling in my head for a few months. I set up the domain, e-mail addresses, even a WordPress account and left it to simmer. My single life has been a long string of crazy and interesting stories shared with close friends over drinks. Many of these tales I was afraid and ashamed to admit. I was frustrated by being single in New York City, it’s really hard to talk to friends (who don’t care about being single or happily with someone) about the craziness that goes on in my single life. Sometimes I feel as if I’m preaching to the choir, other times sympathizers, but more often than not on deaf ears. I love my friends, but we share tales to get it off our chest and chuckle over what happened during drinks. Afterwards I go home frustrated, alone and wanting to scream at the top of my lungs at the fate that was handed to me. A fucked up singles life.
So a month ago I acted on this idea, detailing my single life, my thoughts about being single, and now I wish I’ve done this sooner. Not only has my life as a single improved, the sharp pain that is singledom feels a bit dull. Who would have thought that I would have learned so much, met so many awesome people and feel better about being single in only the first month? I didn’t.
So a month has passed of what is going to be many, many months and I hope you’ve been enjoyed reading so far! I really appreciate your comments, suggestions and helpful insight. There’s plenty more to come!
Tagged As: Personal Details
Single Life
Published On: September 24th, 2009 by Single City Guy | 2 Comments
One of my major dating flaws is approaching and introducing myself to women. I’m “old-school” when it comes to an approach; ask for their name, throw a compliment and work from there. In todays modern world, this approach is just as successful as using the line “Hi, nice shoes, lets fuck!” Most people suggest using an approach to gardner her interests into you as a person, such as displaying your humor, wit or intelligence. Afterwards it’s all up to you. I begin to falter right after gardening a person’s interests, usually when you tell the person your name, likes and dislikes.
A few of the reasons I falter is I get so wrapped into the conversation, I forget or take the opportunity to formally introduce myself; I become just another guy. Here’s perfect example, 5 posts in and I’ve yet to tell my readers (who seem to be predominantly female) anything about myself. I’ve dropped some hints but nothing direct. So it’s time to introduce myself. [Read The Rest Of This Entry]
Tagged As: Dating Techniques, Introductions, Personal Details
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