Exploring Posts Tagged

Rule Breaker

Dating

Lessons Learned From Breaking Up

Published On: October 20th, 2010 by Single City Guy | 4 Comments

Math lessons on a chalkboard

I don’t want to dwell on my breakup with Rule Breaker for many reasons, including that I don’t want to be “that guy.” The person who cries and moans about their previous relationships until everyone is sick of hearing about it. Life doesn’t revolve around how a relationship succeeds or fails. That’s not to say some relationships aren’t defining moments in one’s life. My relationship with Rule Breaker was just that, a defining and important relationship in my life. Now that the book has ended, there are some lessons I’ve learned about myself, relationships, and what to do next time. [Read The Rest Of This Entry]

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Dating

Breaking Up Sucks

Published On: October 15th, 2010 by Single City Guy | 7 Comments

A couple separated

After 8 months, Rule Breaker and I are no longer together. Had this been the case of a bad relationship, I would be quite overjoyed and thrilled. However what problems caused the end of our relationship doesn’t overlook the fact that this was a food relationship with a great and wonderful woman. I can’t help but to be a bit sad. [Read The Rest Of This Entry]

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Dating

From Rule Breaker to Girlfriend

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]

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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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