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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]
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]
I’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]
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]
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.
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]
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]
This is the most complex blog post I written about any date. As Single City Guy, I have the luxury of writing anonymously about my dates, remaining honest about how well they went, and not worry that my dates are going to read them. If they happen to stumble upon it by chance, I have the ability to deny it was me. This post is different, I do not have that luxury here. I’ve entered a situation where a woman who I’ve gone out with twice knows my dating alter-ego. Here’s how it happened.
Last weekend, I went on a NDD with @KB_in_NYC who suggested setting me up with a friend. Blind dates have never worked well for me, but I was convinced I had nothing to loose about and threw chance to the wind. We were introduced thru Twitter, but thanks to a series of mishaps, I was introduced as SCG. I’m sure it’s odd being introduced to an anonymous dating blogger as a blind date. For me it’s even worse, I’m faced with two choices: either write about the date and fear she’ll read it; or don’t write about the date, be dishonest to your readers, and deal with questions later. [Read The Rest Of This Entry]
I really have underestimated Ex-Party Girl (XPG), she’s slowly becoming more than I thought she would, but quickly becoming a friend. Yes, she’s entering my friend zone. The third date is usually the do or die date, where a kiss or something would happen. It didn’t happen on my 3rd Date (or if you’re counting the 2nd real date.) I called the dating coach for some pre-date advice and understood what I had to do, this time I had to be flirty and see how she react to it. However we ended up doing the same thing we’ve done on the past two dates and that’s talk and ask each other questions. [Read The Rest Of This Entry]
I’m willing to admit when I make a mistake, and I think I was about to make a mistake with ex-party girl. When we went out for our pre-date, I wasn’t too attracted to her but there was something there. Her pictures on OkCupid didn’t help out her cause too much. She’s not a 10, but definitely not a 5, she hovers around a 6 and 7, which in my opinion is C List territory. On our first-date (second meeting), I was reminded why I like this girl, it’s her personality, the ability to have a great conversation, and we really get along. I like being able to be honest with someone and to be myself; she allows me to do all of these things. But… [Read The Rest Of This Entry]
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