Greg is Dating

I met Andrea about a year ago, when she walked in the new dance class at my gym. A colleague and I had decided to check it out. Then in comes this very beautiful, extremely fit, dark-skinned lady, dressed in a revealingly tight dance outfit, who of course turned out to be the instructor. I couldn’t take my eyes off her for a while; but what of it? I was still in a (dying) relationship with Dharma, plus I was nowhere near the comfort level I am now when it comes to chatting up beautiful women.

I loved her class. I soon became a regular, attending every week, or at least whenever my schedule would allow it. But it wasn’t until recently that I felt comfortable enough around Andrea to even start a conversation longer than “How are you today?”.

      

This is where I reap the benefits of my personal journey over the last year, which I have been chronicling in this blog. In the past, I wouldn’t have had the courage or the confidence to approach a woman like Andrea, unless she had demonstrated her interest in me first in some way. But there was no chance of that happening with Andrea: she is not one to let show interest in men, or ever make the first move, even though, as she later admitted, she actually had a crush on me almost since the beginning. But my experiences over the last 6 months have taught me two things, if nothing else: 1) I cannot get anywhere if I don’t try, and 2) I have nothing to lose. Elementary my dear Watson, you will be tempted to say, but it’s shocking how many men (and in fact, why confine this to men? Rather, how many people) let fear stop them from even as simple a task as talking to someone.

Andrea has a habit of arriving early for her class, and I usually do some weights before the cardio exercise. Initially, this gave us the opportunity to exchange some pleasantries. Eventually, I decided to stay behind after a class to chat with her. That turned into an invitation for a drink, which Andrea happily accepted. Very quickly we found that we shared a good connection. Andrea told me all about herself, including a couple of facts that surprised me. One was that she is 34 years old. I had assumed from her toned physique and youthful appearance that she was around 28. The other was that she has a 5 year old daughter.

Quick aside: I have said before that I have a rule against dating women with children. The fact that learning about Andrea’s daughter didn’t phase me for more than a minute, should still not come as a surprise. Experienced readers will know that when men say that we have strict rules about the way we live our lives, what we actually mean is that we do have strict rules, unless a hot woman is involved.

And Andrea is hot. Oh god, is she hot! She is funny, she is smart, she is fit, she is beautiful, she is a great dancer (well, duh!), which is a huge bonus to me, and even though muscular women are not everybody’s cup of tea, her very toned and defined body makes her unbelievably sexy to me. She is also a fun person to be around, full of energy and thirst for life, while at the same time being a responsible parent who works two jobs. Suffice to say, I was smitten.

We renewed our plans for a drink after the class a week later, and that’s when I knew I might be getting somewhere with Andrea. She made a very obvious effort to dress up even though it was just a casual drink after work. She also really opened up to me about her life, problems, and future plans. Andrea told me about an open-air dance event on the beach she was going to the next weekend, and I said I would check it out with Cyrus, who was in town at the time.

Fast forward to that Saturday, and Andrea and I only had eyes for each other. We spent the entire evening on the dance floor, pretty much ignoring our respective friends, who had no other choice but to get to know each other better! Eventually, we took a break and  walked to a nearby bench to catch our breaths. Which we didn’t, because before we knew it, our lips were locked and the rest of the night went by with a lot more kissing than dancing.

The best thing about Andrea was that from the very beginning she made me feel like I was really special to her. I was going out with a couple other women at the time, but I instantly knew that I would rather stick with Andrea. Cyrus said it best, when he saw the change in my demeanor: “She has blown everyone else out of the water, hasn’t she!”. Well, yes, she did. I decided to break it off with Lauren and Ruby as soon as I talked to them next.

Andrea has a daughter to take care off and a full-time job on top of her dance lessons. This meant that, at least in the beginning, we only got a chance to meet once a week or so, if we were lucky. That first week, we weren’t. I was going to be traveling out of town. Andrea and I made plans to go out together the weekend after my return, two weeks later.

I am not going to lie: I couldn’t wait for our next meeting.

A few weeks ago, I was at a birthday party in a bar with my friend Alex. I didn’t know anyone there; Alex was the one who knew the birthday boy, as well as many of the guests. I did my best to mingle with the crowd; it wasn’t difficult since we were late to the party and everyone was already pretty buzzed. I went back and forth and got to know some of the people there. As I was talking to one group, discussing a performance several of us had attended earlier in the evening, Shilpa walked into our company.

Shilpa is the businesswoman type; straight and fast talking, a go-getter, and full of nervous energy. She is an Indian woman in her 30s, with an East coast, no-bullshit attitude. Not surprisingly, we quickly hit it off, and when she left early, I asked for her number so that we could continue our chat another time.

I called Shilpa the next day, and our rapport carried through on the phone as well. Since we seemed to have a lot to talk about, I asked her out for dinner on the same night, and she happily accepted. We had a very nice evening. The food was great, the cocktails excellent, and the company delightful. Shilpa soon got comfortable in the corner booth we were sharing, putting her feet up on the couch. For the rest of the evening, I was touching her legs and feet or her hands as we were talking. When we left the restaurant, we were holding hands.

When it comes to women, I am generally a bit shy and timid. For this reason, I often have difficulty taking the first step, like a kiss, unless I am certain that my company feels the same way. With Shilpa the signs were all there though, and as I was walking her to her car, I leaned in to kiss her. I was therefore very surprised when she pulled away. “I want to get to know you better first” is all she said, before she wished me a good night.

                         

Refreshingly, we stayed in regular touch with Shilpa through phone and text. A few days later, we went for dinner again, and once more we had a very good time. Afterwards we took a walk along the water and kept our discussion flowing. Again, all the signs were there and it felt right, and had things been different, I would have kissed Shilpa right there and then. I didn’t try anything, respecting her feelings, but I did share these thoughts with her.

Shilpa appeared keen to keep meeting, which I appreciated because, sadly, I have grown accustomed to people being aloof and distant. We made plans to go to a dance performance on the following Thursday. Three days before that, she called me and invited me out for drinks with her colleagues. Afterwards, I walked Shilpa to her car, and even though I knew her feelings, for some reason I really cannot explain I tried to kiss her once more. And once more she avoided my kiss.

And with that, the keenness ended. There were no more texts or calls for the next couple of days. On Wednesday, the evening before out planned date, she called me to say that she wanted to cancel our tickets and that she thought we were looking for different things. I was not surprised. I thanked her and we said goodbye.

I do not blame Shilpa for the way things ended. We were not at the same place, and that’s all there is to it. I did take one thing out of the experience: the realization, or rather, the reminder, that I am not a patient man when it comes to women. I need things to progress quickly. Sometimes, this is mistaken for pushiness, or even for having a “one track mind” and only thinking about sex. This is not the case (even though I do, admittedly, also think about sex!). I am just an enthusiastic person; I get very excited when I meet someone new, and I need the other side to also show some excitement about me.

Sometimes, my enthusiasm leads to misunderstandings. Sometimes, it leads to regrets. But I have decided it’s much better to regret the things I did, than the things I didn’t do. I try to apply that rule as often as possible.

I met Carla at a networking event for singles at a downtown bar. I was there with a bunch of friends and we were having a grand time, when she tapped me on the shoulder and introduced herself. Carla is a tall, busty brunette with a big smile and a wonderful energy that I immediately found attractive. We chatted for a while that first night, but Carla lives 50 miles out of town, which meant she needed to leave relatively early. I asked her for her phone number before she left, and we agreed to make plans for the upcoming weekend.

Things got in the way, and Carla and I didn’t manage to see each other again for a couple of weeks. But eventually, we arranged to meet for salsa on a Saturday night, one of those one-hour class, then dancing for the rest of the evening events. Carla was there with a group of friends, most of them male it seemed, and it became clear that several of them were interested in her. This only occupied my thoughts very briefly, because soon it was obvious that Carla was in fact interested in me. She even told me how nervous I made her when we danced together, but she didn’t need to, I could see it written all over her.

I consider myself a decent dancer, but irrespective of personal opinion, the important part is that Carla was very impressed with me every time we danced. Other people cut in but that was OK, Carla kept coming back to me every time. After a couple of hours of this, and when we had finished dancing once more, I asked her to walk out with me for some air. She agreed. I took her by the hand and led her to a little park across the street from the salsa place. In the middle of the park, with dim lights and the music and noise from the bars in the distance, we kissed for the first time. A very nice moment, if I can say so myself.

      

Carla had to leave early once more, so we eagerly made plans for dinner during the next week and we kissed goodnight. Alas, that would prove to be the highlight of my association with her. I had broken many of my rules in trying to date Carla, but I overlooked this because she was showing a lot of interest in me and even actively pursued going out on dates, which was a pleasant change of pace from the usual dating experience for me. But in retrospect, the red flags were all there. She lived too far away, and I have a rule against dating women out of town. I also have rules against women with children and women in the middle or just out of divorces, and Carla was both of those. I know you are saying to yourself now, Greg, you might have wanted to mention that a bit earlier in the story. Well, the fact is that this information only came out on a phone conversation after our salsa date. Thinking about it, that was yet another red flag.

Carla and I were supposed to meet for dinner on the Tuesday after our salsa evening. The day before our date, she called and cancelled, saying she would explain her reasons when we saw each other next. Later in the week, she called me to make new plans, so we scheduled dinner again for a week later. Our date was on a Friday night, and I was about to start getting ready for it, when Carla texted me to cancel once more. This time she said that her divorce situation is taking too big a toll on her and she has decided she is not ready to date yet, so she would not bother me anymore. I replied that I understand, and that she can always give me a ring if she wants to grab a drink sometime when she is in town.

Her reference to her divorce was my first indication that Carla was still in the middle of it, or even affected by it in any way. I would certainly not have pursued dating her if I knew this from the beginning. I hold no grudges, and even though this is very recent (our last canceled date was for yesterday) I do not feel particularly disappointed. Part of me wants to believe that I was simply never very interested in Carla. Part of me is afraid that I am beginning to become jaded by the whole American dating experience.

My posts have almost caught up with real life. I have decided on occasion to tell some stories from the distant past, or at least outside the period from October 2011 to the present, which my blog normally covers. Here’s my first try. I hope you enjoy it!

I was still living back home, a year or two before finishing my undergrad degree. Ollie was my brother’s colleague in college. I met her at their graduation ceremony. She apparently had heard a million stories about me from my brother, I couldn’t even remember him mentioning her name. Or maybe I was just not paying attention.

I no longer recall how it happened, but soon after that I had a second run in with Ollie. I must have asked her for her number then, because a few days later I called her and asked her out. Her reaction was the most strange and awkwardly flattering I have ever gotten in that situation: she was genuinely in disbelief that I would ever consider going out with her.

We met the next day, but only after Ollie made me promise that it would remain a secret between us. She had been close friends with my brother for 2 years, and she was uncomfortable about dating me if he knew about it. I remember having a good time with Ollie that night. And for some reason, she was in awe of me, especially intellectually. I believe it was the result of seeing me through my brother’s eyes; he has always looked up to me as his older sibling.

A week later, and after going out a few more times, I took Ollie home. My brother and I were still living with our parents at the time, so I made sure everyone was out for the evening. We were there with a purpose, so we quickly started to kiss and undress. We had sex for the first (and what proved to be the last) time on my brother’s bed. I guess it felt more naughty. As these things go, it ended up being a strange mix of trying to savor the new experience and harrying through the motions so as not to get caught by a member of my family.

The sex with Ollie proved to be underwhelming. In fact, I will go as far as to say it was the worst I ever had. I’ve never thought it was either her or my fault; I have always assumed that simply there was something missing between us. The bad sex was one reason I broke it off with her soon after, the other was her constant adoration of my mental faculties, which was cute in the beginning, but wore thin very, very quickly. I am stubborn and argumentative; I confess that I do love a good argument. Often, this makes people think I am the kind of person who always needs to be right. I have been told in several occasions, even by family members or ex-girlfriends, who are supposed to know me better, that I would be happier with a dumb girl, because then I could win all the arguments. My experience with Ollie is more than enough for me to know better.

What happened between Ollie and me remained a secret for several years. A year after our short-lived affair, she actually applied for a job in my father’s company. She has been working there ever since, first for my father, and later, when my father retired, for my brother. Today, she is married and has two children.

Years later, I was on vacation with my brother, and on a cool summer evening on the beach, I confessed this story to him. He is the only one who knows about it. I never told him about using his bed though. I wish I could remember if I changed his sheets.

I met Sun in one of the speed dating events I attended. After the initial emails, we exchanged telephone numbers and arranged to meet on a Sunday evening at a wine bar. There is nothing extraordinary, good or bad, to report about this first date; we had a couple of glasses of wine and got to know each other a little bit.

Our date was on the same day as the 2012 Academy Awards and, in talking about the Oscars, we found out that we both still had not seen the Artist. I offered to take her to the only theater in town that was still playing the film, so we renewed our plans for the following weekend.

     

Sun is Asian, in her early 30s, and very short and slender. I am generally not attracted to small women; my size makes me feel uncomfortable around them. Nevertheless, I thought I’d give it a chance. On the day of our second date, Sun and I met near the theater, had a quick drink before the film and enjoyed the Artist together. After the end of the movie, I suggested another drink and maybe a quick bite. Sun agreed, and I led her to a speakeasy-style bar that is all the rage in that neighborhood.

We started talking about our childhoods and our families, and we actually had a good time from then on. The evening seemed to be going great, until each of us made a faux pas. First, Sun told me about an ex-boyfriend of hers, who as she told me was gay. They dated for about a year. I didn’t know what to do with this information, and I was taken aback for a while. As the conversation was recovering, it was my turn to put my foot in my mouth: I really can’t remember anymore exactly what I said, but I made some sex-related joke. I do not think it was anything really inappropriate, I imagine I thought it was funny at the time, and I probably would still find it funny today, but what is important is that Sun clearly did not appreciate it. Things got weird after that, and we called it a night. Sun demonstrated how uncomfortable she felt by panicking when I tried to kiss her goodnight, even though I was really aiming for her cheek. I thought that was pretty funny.

The next day, I got a message from Sun saying that she did not think it would work out between us. It sounded about right.