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.

I last saw her on Tuesday for our second date, it was now Friday and I was on a third date with her. I had a fear this was too much to quickly. My fears began to subside when I saw her. Everything began well, but during the date she made a comment that made me evaluate the process of dating. It also made me realize where I’ve failed in the past. While eating, she mentioned that I didn’t reveal much about my family or some of the things that would make her get to know me better. It’s one thing to talk about your day, and what you think will happen in a relationship and your likes, it’s another thing to talk about intimate details at length. The third date seems to be the starting line for this process.

When discussing yourself and these intimate details, not only do you get to know a person, but you get past some of their insecurities. You begin to get the temperature of the relationship you have in front of you. Will this person last long term? Is she a short term relationship? Is this only about sex or more? The discussion and interaction becomes the most important aspect of the third date, regardless of the venue. It’s about developing intimacy.

Now the third date went fairly well and was simple, dinner at a restaurant. Discussion over wine and pasta. It was simple, but intimate. After dinner we left and were both headed in the direction of her apartment. The train station was on the way. I was going to ask if she wanted me to walk her home, but she caught me off guard by inviting me to her place before I got the chance. It was an awkward invite, but cute, genuine, and one that I accepted.

Now, my faithful reader, you may make a few assumptions about what happened next, but what you think and what occurred are two different things. As much as I want to go into detail, I will say this; I left her apartment satisfied without taking my or her clothing off. I didn’t have sex with her.

Why not? Two reasons: first she wasn’t ready (and to be honest, neither was I) and second, if I’m seeking a relationship with her sex can wait. Who cares when sex happens, getting to know someone, enjoying your time with them, and having intense moments without sex is possible and most important. When you have sex too early, the relationship becomes about sex and not the person. It’s the foundation of Steve Harvey’s 90 Day rule. While I disagree with the timeframe, I agree with the principal.

It was clear, after the third date, that she was going to be around for a while, and I enjoyed the notion of that thought. As I left her apartment, I wanted to run back up and kiss her again. I was jubilant, excited, and began texting a few people immediately.

I knew that soon, I would have to call Rule Breaker by a different name soon.

Photo by Alison Narro

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.

Now, logic would dictate I was screwed the pooch and had no chance to ever see this woman again. I keep advising women if a guy is interested into you, he will call within the first week of meeting you. Afterwards, you haven’t a chance. Life happens, iPads get released after the first date, and our time, much like yours, becomes tied up. I know women have a smaller window (2 to 3 days). It’s almost as if they have a shot clock in their homes that counts the days down. In all honesty, if a guy likes you, he will call within a week, more than likely twice if he didn’t reach you the first time.

I called again on Monday, the day before our possible second date. I was getting worried and unsure of what was going to happen. I enjoyed my time with her on the first date, I had to be sure I would see her again. After work, I made sure I dialed her number, and this time I struck gold. It was a huge relief when she picked up. We talked and I apologized for not calling sooner. She understood, telling me she had left me a voicemail and reminded me that she was out of the city for the weekend. My phone suddenly buzzed in my ear, indicating I had just received said voicemail. We talked for a bit and arranged date number two, which would occur at a place she had mentioned and I was interested in seeing.

I arrived, and we talked, had a drink, and enjoyed each other’s company. During the first twenty minutes of the date I was a bit out of it, not sure why. She was her interesting, attractive self, we clicked well, but something was wrong, felt wrong. It wasn’t her, it was me. I later realized that I had gone into this second date expecting failure, most women I liked hadn’t gone past the second date. I had to shift my gears to ensure this date would go well, I had to think of this date in terms of success rather than failure.

After a drink, we decided food was in order, and there was a burger place, not to far away. In leaving the place, we walked thru a park, where I insisted we walk arm in arm. I think I mentioned if this date was an actual date, we should act like it. I don’t quite remember the wording, but soon her arm was hooked with mine. I was happy. When we arrived at the place, she mentioned we should sit by a window. I liked the idea. The restaurant had these large ceiling to floor windows that peered outside. It was beginning to snow, which made the scene a bit magical. The problem was, there was another couple in our potential seat. The hostess told us they were about to leave, and we could wait at the bar.

Time passed, and they were still seated in our seat. We began to wonder if we should just sit somewhere else. We both had a goal in mind, window seats, and were willing to wait for them. So we did. More time passed and the hostess seemed to join in the fun, wondering what was taking those two people so very long. She went over and assisted in securing our seats, and even placed a reserved plaque on the table. It was a cute, memorable happening.

Dinner was great, as we delved into more personal subjects. I almost let loose my secret at SCG, but stopped and mentioned I had a dating coach. She seemed to take it in stride, although I was tripping over my words. After dinner, I walked her to the train station. We were taking the same trains, but in different directions. We talked and walked, with the snow falling on us, arm in arm. Suddenly she slipped, I clenched my arm, and she held onto it, making sure she avoided hitting the pavement. “Wow, you’re strong!” She said. The ego boost shot thru me like adrenaline, I had scored major points, but still had an unfinished task.

I wanted to kiss Rule Breaker. I had since the first date. When I told a friend, she reminded me to man up. “If you want to kiss her, kiss her damnit!” She told me, and she was right. When we reached the train station, and were about to part, I had two options, either let her go without a kiss or take this as my final opportunity. We hugged, and I placed my hand in hers. Soon after our lips met, in a short but great kiss that struck me to the core. What ever armor I had was blown right off, I was putty at the moment and I let her know it.

I had reached success! I set my goals for the date and had met them with a woman I found attractive. This was a good sign, a very good sign. What made it even better was, I would see her again in a few days.

“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.

Like everything with her, the date did start awkwardly. I arrived early at the negotiated date location, Madame X. I’ve always wanted to use this bar as a date location, just to see how it would work. She was also in the area, so the opportunity had finally arrived. I came to the date with a limited amount of knowledge about her physical appearance. She only had head shots in her profile, and I was in a poorly lit area. It was going to be hard to figure out who’s who. I stood near the entrance and waited, until someone who seemed like it was her was going to walk into the bar or was waiting for someone. A woman did slow down and began to look around. I called my dates name out to that woman, figuring it was her.

I was wrong. “No, I’m her!” A voice I had recognized from my phone conversations said behind me. Obviously it was my date, and the beginning of another awkward, but humorous line of events to follow. Throughout the date, I could not stop laughing and smiling, so much that my checks hurt. It wasn’t any one thing in particular, just the way we talked and meshed seemed to work very well with one another. I don’t think I’ve ever laughed that hard on a date. Ever.

Rule Breaker is an attractive woman, who laid it all out there. I didn’t feel as if I was navigating thru that mental minefield women often put guys thru. She has very varied tastes, like myself, fun, eccentric, speaks off the cuff, and most importantly honest. What surprised me was how attracted I were to those qualities she had. I found her type of honesty sexy, the fact she spoke her mind and didn’t hind behind an excuse. If we disagreed she would give me shit for it, but playfully, and it made me laugh. Another attractive trait she had was her ability to relate to what I was saying, without understanding exactly what I meant. I’m a geek, and made a few geek jokes – one was calculating the differences in ages between me and my siblings. It took me a moment to remember the age differences because at any given time there’s an additional year difference. I joked it was like computer code, and made a code joke (“if before the month of April but not after the month of June relative to the suns positions based on the hypotenuse of y then minus….”) She’s not a coder at all, but understood he joke, and participated! She later said, “I don’t get it, but I get it!” The same thing occurred with a sports references I made. While I’m very attracted to women who love sports, she’s not a sports fan, but makes sincere and honest attempts to get the reference. That blew me away.

As I got to know her better throughout the evening, I realized that Rule Breaker was the type of woman I’ve sought for, but have passed up in the past. Not because I wasn’t attracted to them, but because I felt so comfortable with them they would become dear friends of mine. She reminded me of a few friends, all whom I wanted to hook up with, and I realized I wasn’t going to make the same mistake with her that I have with other women. I wanted to see her naked at some point, and had to be sure I made that fact known. As that thought went through my head, I was reminded of something Thomas and Laurie taught me, introducing some sexual tension.

To introduce some form of sexual tension with a woman, you must do it with touch. This should be subtle, say by touching her leg or arm. Not a poke, but more like laying your hand on her leg while making a point. I did this repetitively throughout the evening, all naturally and not frequent enough that it got annoying. She responded a few times with her own touches on my leg or hands, which made it feel as if I was on the right track. It was clear that the signals were sent, we both like each other!

After a great date, two drinks, it was time to go home. I walked with her to a train where we separated and went our separate ways. She went uptown, I went downtown. We hugged and parted, and tentatively set up a date for the next week. Moments later I was kicking myself a bit, I wanted to kiss her. I was going to have to make sure that happened on the second date, which meant calling her soon.

Photo by Jenser (Clasix-Design)

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.

Things began with my new focus on finding profiles on OkCupid. Using the techniques I’ve learned from Laurie, I began sending some of my own e-mails to the women I had common interests. Rule Breaker was one of them, and after two rounds of shorts e-mails, she asked for my phone number. Traditionally, women prefer the guy to ask for the phone number, I’ve learned there needs to be more than two responses before asking for a phone number. This woman was breaking the rules (hence the name), and had the cajones to ask for mine. Her upfront brashness intrigued me. Stupidity I sent along my phone number without asking for hers. Things were entirely in her court.

She called me sometime the next evening, but I missed her phone call. I was in the shower. I returned her call after listening to her voicemail, only to be met with hers. I hate leaving messages. After adding to the weight of her voicemail, I had hoped she would call me back within mere moments. I had only missed her by 20 minutes! While I was lucky to get a response, I was also lucky to be underground when she called. My phone beeped that I had a message eagerly waiting my ear. I responded the next chance I got to her voicemail leaving, yet, another message. A few days passed, and another round of tag ensued as we missed each other by mere moments, minutes, and hours. This was the classic case of unaligned schedules.

The last round occurred during a late night meeting. While heading to the meeting, a deposit was placed into my voicemail. I was, again, underground, and unable to response. I responded with a message when I arrived at the meeting’s location early. She called 20 minutes later, during my meeting. I didn’t hear the phone at all. After the meeting, I listened to the message, only to respond only to be met by her voice. It told me to leave a message because she wasn’t able to reach the phone. I was in voicemail hell. This situation was becoming humorous. I’ve had more interactions with her voicemail than her; it seemed as if I was dating it. Imagine me, on a date with a voicemail box.

“How do you like the food here?”

“You have 1 new voice mail message!” It would respond as a sign of approval. I’ve always wondered if the woman who does the voice for voicemail is attractive.

After my meeting, I was heading to the Apple Store on 5th Avenue, but was on the West Side. When I exited the Columbus Circle train top, I would have to walk a distance to 5th Avenue. This game of voicemail tag was becoming annoying, I had called her a mere 30 minutes ago, but what harm would another attempt  do? I could start reciting lines from Shakespeare as a part of my voicemail messages! As I began to rummage my mind for some line from Macbeth, I was dialing her number, and the phone was ringing. It rang once. No pickup. Twice. To be, or not to be. Three times. I’m definitely getting the dreaded voicemail void all over again. Shit, what was the rest of that monologue?

A friendly, and awkward, “hello,” interrupted the trip to the dreaded voicemail box. It was a real person!

We talked as I walked to the Apple Store, and continued to talk while I stood outside, in the cold. I wasn’t going to pass up on this opportunity to talk to and meet this woman. We laughed with each other, had a great conversation, we seemed to mesh well over the phone. It was obvious a date had to be made. This was more than just fighting for her attention, this was being persistent.

At any given time, I could have given up, allow the fade to set in or find some reason not to pursue the frustrating game of tag. The only thing I knew about this person was our many interests. Her profile only included headshots, so I really didn’t know what she looked like. What drew me to this woman in the first place was a single commonality we had, the diversity in the things we did in our daily lives. Statistically, this shouldn’t have gone anywhere; she should have disappeared into oblivion, never to be heard from or seen again. She should be a failed dating story for me to use as an example of what not to do. She isn’t.

One of the few reasons I kept on returning her calls, only to be met by her voicemail, was because I was persistent.  I wanted to meet this woman and there was something worth seeking. This wasn’t fighting for a woman’s attention, I already had her attention. At this point I was fighting against her schedule and her ability to pickup the damn phone. This isn’t the only example where persistence has paid off, just the best example. Skee Woman and PR Model are other examples where persistence has resulted in dating successes. More so than fighting for a woman’s attention, a guy must be persistent. Eager to communicate, making any attempts to talk to a woman, even when the chances of success seem bleak.

So what is persistence in dating, exactly? It’s continuing to make an effort, even when a situation seems to be lost. In my example, it’s calling twice, within an hour, in hopes not to become just some voice in the voicemail.  So far, it has worked.

Image Source: Vanessa Pike-Russell on Flickr

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.

Skee Woman is the type of women man, theoretically, fall head over heels for. An attractive, down to Earth woman, she’s able to hang out with the guys while maintaining everything that makes her a girl. She competitive and is passionate about Skee Ball (hence the name, not a Lil’ John reference). I knew this woman was different when we discussed the day and time for the date. She asked, “How does Saturday at 4pm sound?”

“Hmmm…. playoff Football game or date… date wins.” I replied.

“I like your priorities… I’m a football fan too. We’ll make it work!”

Cue the confetti, fireworks, and dramatic music. I like this woman already!

We met at a bar, that had several Skee Ball lanes, but I had already hit the gutter. I was late, mainly because I left my wallet at home. I was so excited when I was walking out of the door, I forgot my wallet on the table. I had to double back from the train station to grab my wallet, send her a message, and perform my best Usain Bolt impersonation. It’s been made clear to me I’m not Usain Bolt.

When I did arrive, and she was still there, forgave me for being tardy, I offered to buy her drinks (the least I could do). Conversation was easy, I felt comfortable with her and strangely at ease, she knew my current deep dark secret. I knew she was afraid of it when we joked about what her potential nickname. After talking for a bit, we played a bit of Skee Ball. I scored a 90, which is called a “Right Angle” (90 degrees forms a right angle, it’s a trigonometry thing). Before the game, she explained the rules to Skee Ball to me, and while explained the rules and the phrases was completely cute doing so. It’s a passion, you can tell, her face lit up when I asked her questions. It’s the same expression we guys have when a woman asks us about something that really interests us. She did thoroughly whip my ass, it was worth seeing her light up the way she did. After a few rounds of Skee ball we began to engage in more conversation.

Our talks revolved around some of the basics, what we did, who we were, but it also drifted into the area of relationships. She explained some of her difficulties and fears with dating, the ever looming pressure to make a decision the minute you meet a person. Having to choose “do I like them” at a moments notice. A part of me wanted to ask her if she liked me, but I didn’t feel the need to. Of the recent women I’ve dated, I didn’t care if she gave me that type of validation. I truly enjoyed my time with her. If this were to be the only time I saw her ever again, I wouldn’t feel as if there was a loss.

Something did nag at me. She works in the entertainment industry, filled with an office of guys and posters of hot size 2 models. On a daily basis she received doses of what men say when it’s just the guys in the room. The true talks all men have with each other. It nagged me because she could be overanalyzing everything I said, converting it into translated dumb dude talk. Added with the fact that she’s read The Game, knows my identity, she could assume I was trying to run some sort of game on her. So it was a surprise when the said she felt comfortable with me, and how easy it was to have a conversation with me. It was the best thing I’ve heard from a woman in a long time.

It’s not often that you meet unique, quality woman like her. While her being comfortable with me may indicate just being friends, I’m very comfortable with the thought. If that’s the very least of our relationship, I would be happy.

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.

Presentation is everything, especially while speed dating. Something you learn from speed dating is how to best package yourself in a short amount of time. Any man can get the attention of a woman, it’s the presentation that truly matters. In a room filled with 30-somethings, seeking other 30-somethings, and I was making great progress. All the women seemed engaged and interested even though I was 20 something. One woman even bought me a drink. I was being successful at this speed dating event because I was able to present myself in a manner that garnered each of the women’s attention. I was able to connect quickly with them based on similar interests or items that peaked their interests in me.

What made me successful wasn’t that I was interesting, it was that I had something interesting to say. I wasn’t boring these women with the full details of my life. I turned, what would be paragraph long answers into quick snapshot sentences. These quick sentences was bait for the women to ask more questions, if they were interested, or to move onto a different topic. For those interested it worked well, my age didn’t become an issue. Who I was became more important. I wasn’t “gaming” them, I didn’t use any tricks or pickup lines. I was amassing conversations by being myself, honest, but presented it in a way that made them take notice.

Image Credit: darkmatter on Flickr

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.”

“Older Women” Night was another OnSpeedDating.com event I was invited to. Learning from my previous engagements, I decided to arrive early but not very early. I ate and had a drink at my local waterhole hole, blocks away from the event. I was prepared to date and leave. When I arrived I noticed one thing, there were plenty of men. I was even surprised by the type of men there. As I looked around, I thought I would be one of the better catches, but there was serious competition. As far as the older women, the main issue was, there wasn’t enough! There were 12 men and 5 women total. Which means I really had to shine! The 2 to 1 ratio was odd, but this could be due to the holiday season and the event occurring on a Monday. I will note, the selection of women was much better than I anticipated, many were potentials B – Listers, one was an out right potential A – Lister. I will repeat my previous statement, these women were very attractive!

The dating went well, but I did make a few mistakes. With not as many women around, I was able to listen in on the dates next to me. While listening, I was forming a strategy for each date on how I could remain different from the other men in the room. I thought I could lead with a question the other’s weren’t asking. My first date went well, and my plan was working. My second date is where I really messed up. I started with “What was your weirdest vacation?” WRONG QUESTION TO ASK! Just horrible, I should have asked something like, “What was your most memorable vacation?” or “What would be your dream vacation spot?” I could have saved myself, but when asked the same question I lead with a horror story. Bad move.

The third date, I made the wrong connection and tripped up on a few questions. It wasn’t until my last date that I realized I need a different approach. This happened when she opened me up, asking me about my phone. We began to discuss technology and how it’s evolved over the time . I learned something from this woman, I need to do a better job in packaging myself.

As the event ended, I wanted to spend some time with my picks. One of them were being swept away and gave me the brush. Another one did the same thing, but seemed interested. It was clear, I wasn’t getting a date from this group. The lessons I learned tonight however, were invaluable.

Image Credit: muzina_shanghai on Flickr

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.

PR Model is just that, she’s a woman from the pacific time zone who works in PR and is a model/actress. She’s an energetic woman with a great sense of humor, interest and very down to earth. She’s also very beautiful, has the personality and wit I love in a woman, but also a directness and a no-nonsense style I can dig. She’s an instant A Lister. It wasn’t until I met her, the day before Thanksgiving at the Flatiron Lounge, that I was able to learn how unique of a woman she was. We hit it off very well, and we were able to discuss several topics I thought would be a major problems, such as being a dating blogger. I knew I would have to explain why I stared SCG; my frustrations with dating, bad dates, and the material we guys get, such as The Game; came did up, and she admitted to reading (or at leas skimming.)

At this point I did something potentially stupid or really smart. I tried the number guessing game which is a part of the Mystery Method PUA technique (I’ll explain this technique in a later post.) I really was trying to make SCG a non-factor. I wanted to demonstrate that I am being genuine, and not trying some dating techniques I’ve learned or read to woo her. I began the process by having her choose a number, guessed 7 and she lit up! She was so stunned and surprised I guessed the right number she wanted to know how I did it. I quickly confessed to the technique by (which I had planned reveal if I had gotten it wrong.) Although I think plan worked, this could have backfired in my face and ruined everything.

The remainder of the date went on very well, and we scheduled brunch for Sunday (yesterday). She choose the location and time. It was a place we both have not tried. Brunch went well, but a bit rushed, to my benefit I believe. I was nervous and excited leading up to the date and was afraid of a let down from Wednesday. I did have a plan. On the first date, I promised to make her a mixed CD (being a DJ), and give her some music I think she would like. Making these CD’s helped me ease my thoughts about the date and using them as an introduction helped helped ease my nerves. I also hoped it would carry any momentum from Wednesday onto brunch. I think it did, PR Model was very excited to receive the gift. Throughout the brisk meal we talked about Thanksgiving, parades, modeling (did you know there’s a size double 0? It’s smaller than size 0!), plans for this week, and apple smoked bacon (it takes like regular bacon!) I felt brunch was rushed, due to the quick service, but it was a very good date. We laughed, had some great stories and I noticed to things about my interactions with her.

First, she has me wide open. I’m usually not this exposed when I’m going out on a date with someone. I like to keep some cards hidden and reveal them until the time is right. With her I feel as if I’m playing poker and my hand revealed to the world. I cannot hold anything back. This is new territory and it has me off my “game”, but it’s refreshing. I’m forced to be myself, not duck and dodge through conversations, topics, or dating techniques. There are times I mess up where I normally would not. An example was when we were discussing plans for the week, I said “oh right, I can’t do anything on Wednesday because I have to go speed dating…” Yes, I’m an idiot. This is not my proudest moments. What was cool is she understood it as something I have to do as SCG and we still planned to see a movie later in the week. This is a good sign.

Second, there are these awkward silences. Thomas Edwards (@URWingman) advised me on this issue when he was last in NYC. All conversations have an end and a break. These silences are pauses where one topic has ended and a new topic can begin. It’s a lull, that doesn’t need to be filled. They have a place and when they occur I should remain patient and recognize it. I’m struggling with this aspect, because these lulls scare me. I feel like once we hit a pause the momentum stops and I’m lost. So I begin thinking, forming rapid fire questions and being to play a game of hit or miss to get back on track. In the past I’ve made my biggest mistakes here, trying to overcompensate for what would be a really great time. Now I realize when I may be going overboard or hit a dud topic, but it still doesn’t stop the tendency.

So far, PR Model has been the best dates I’ve had. To say that I’m excited and intrigued about this woman is an understatement. Interesting and unique woman like her are hard to find. I would be a fool to not give my best effort here. Before I can do that, a part of me has to calm down and not to become so intoxicated that I loose complete control. Doesn’t mean I cannot be excited! Which I am!

Image Credit: Ammar Abd Rabbo on Flickr

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.

We went to a bar, we’re both familiar with and had drinks on their couches. You would think the kissing would ensue. It did not. There was more talking, more joking. I took initiative to touch her, placing my hand on her leg, leaning into her. I would playfully slap her on her arm with the back of my hand, but she would return the playful slap. A 5 minute playful slapping contest ensued, but it also brought out laughter and giggles. In the past this has worked to break up some tension, it even lead to a make out session. This time, no such luck. Throughout the evening, with all of the touching, she would lean in, then pull back. It was a weird dance, a very uncomfortable dance.

The uncomfortable dance got even more uncomfortable when one of my old time female friends appeared. I’ve known her since middle school and every so often she pops into my life. Never has she popped into my life on a date. I may have overreacted when I saw her (think shrieking high school girl.) There’s also a tiny bit of history between us, good history. Maybe it was a sign that XPG isn’t the one and I need to think of her more as a friend.

It’s that thought that’s what tripping me up now and it’s getting clearer every time we date. We’re still poking and prodding at each other, almost as if both of us are scared to make a move. I’m not all that inclined to make one, she’s a really cool girl and I’m becoming “comfortable” with her. Hence why she’s falling into my friend zone. My instincts are telling me while I think she’s cute, the more I get to meet her, the more I like her opposed to smitten with her. What’s fucking with me is the fact that she’s in the very same position (I think).

Update 2:13pm: One thing I forgot to mention, that got asked on Twitter. I did try to kiss her at the end of the date, but ended up with cheek. In my mind I was thinking about kissing her, but someone turned, and cheeks her landed upon. This was, however, the first kiss of any kind between the both of us.

Our first date went pretty well, after not being able to locate each other on the Manhattan side of the Brooklyn Bridge (we were on opposite sides of the street), we began our date by walking over the bridge. This was the first time I’ve done this with any girl, but it provided an opportunity to walk and talk, I pointed out a few things to her (I completely forgot to point out the Brooklyn light building.) It was cool, simple, and it allowed the both of us to decompress from a long day. Afterwards we went to a place I know in DUMBO for food and drinks.

A few things came up here, first we both like each other. She finds me dateable (which is great!) and attractive (which is even more awesome), but she has some additional questions and concerns for me. I’m in the same position, I think she’s cool and I have an attraction to her, but have my own set of concerns and hesitations. We were honest about how this could and should proceed, forward but with caution. I like that position, being that, dating wise, I’m still trying to figure a lot out, I need some time to gather my own thoughts before this (potentially) turns into a serious relationship.

I did make some mistakes however. I found myself not kissing her, not even on the cheek. I think I should have done that. We hugged but I felt a bit awkward thinking about it, or even doing it: 1) Because I locked up (to kiss, don’t kiss?) and 2) we just had a conversation about how we’re both unsure how to proceed. The second mistake was trying to rush her away. We both took the same train and got off at the same spot. She lives near the train stop, I had to wait for another train. She waiting for me when I totally expected her to go her merry way. So we hugged twice. It was an awkward moment but a good awkward moment.

Ex-party girl has gone from C lister to a low-B-List, she’s a quality woman. you don’t turn down quality women. There’s more to her than meets the eye and I expect to see more in time. Right now my feeling about her is “we’ll see.”