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.

My trip to Cleveland made the situation clear. While I was out bar hopping, I met a tall bartender with the largest breasts I’ve seen in person (I’m a boob guy!) She was attractive, had a great figure and in most cases I would be all over her! I wasn’t feeling it, I didn’t want anyone else to come with me to my hotel room unless they were Rule Breaker. She had me sprung.

When I got back to NYC I had to see her again! I lugged broken luggage up a few flights of stairs only to kiss her and soon after ask her to be mine! Definitely one of the happiest moments in my life!

So in just under six months, I went from dating and frustrated to happy and someone’s boyfriend. How I got there has been a frustrating and interesting ride.

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