To cheat or not to cheat?

It seemed like everywhere I went this weekend I was confronted by some sort of relationship deception. The timing was interesting because I thought about Kay a lot this weekend and what my intentions are.

Friday night I met my sister and her friend out for drinks in Georgetown. The friend, Briana, is young, just 21, and living in DC with her sister for the summer. Though young, Briana was very mature and a lot of fun to hang out with. We played pool at the bar and flirted and eventually decided to meet up the next afternoon for a motorcycle ride. Briana mentioned that she had a boyfriend, but that it wasn't serious. My sister would later tell me that Briana has been dating the dude for three years, which sounds semi-serious to me. I would not be happy if my girlfriend of three years went out on some random dude's bike. In the end we were both too hung over to ride Saturday, but she asked for a rain check.

Saturday night I met up with Randy, who is one of my good friends from college and was in town for the weekend with his wife. Randy is a smart, successful guy and the ladies love him, but that seems to be his downfall. If women were drugs (and let's face it, they basically are), Randy would be a full-blown addict. I've known Randy and his (doctor) wife for a very long time, but in all the years I have never known him to be faithful to her and it bothers me.

After a few drinks Saturday night Randy told me about some douche-bag in Texas he has been having a relationship with for the past year. He met this girl (let's call her DB) while traveling on business. DB is married with two kids, and as far as I'm concerned the only thing that DB has going for her are her body and her looks. She uneducated, and clearly conniving.

The situation is that DB was trying to talk Randy into leaving his wife for her. DB had separated from her husband and wanted to be with Randy, and much to my surprise, he was actually considering it. However, he came to his senses when he found out that DB was fucking some other guy at the same time. It wasn't until then that he felt the pain that he has been causing his wife this whole time (she knew about some of his affairs).

The final aspect of my weekend that rounded off the deception theme is that I met up with Bear last night. We had been emailing each other for a few days and we planned on meeting up. Bear really likes my dog, so she asked if we could take the dog for a walk last night. In typical crazy Bear fashion she showed up in a tiny little skirt (it was so short I couldn't NOT see her underwear, it was very uncomfortable) and pump heels. Not exactly dog-walking attire, but that is pretty much normal for her. I think Bear is/was dating some guy, and if she still is he probably wouldn't have been too excited about her hanging out at her ex's house in a skirt the size of a headband.

We walked the dog and had a beer back at my house. She looked really good, and of course I would have slept with her in a second, but neither of us made any moves and she left around 11pm after a hug.

So, now onto Kay. As I said, I thought about her a lot this weekend. I talked to Kay on Thursday night and she told me that despite some tough deadlines at work she was going to NYC with some girlfriends for the weekend. After I got off the phone with Kay I thought about two things: what is it about her that I like, and what is my plan.

It is necessary to note that I have not had a girl break up with me in nearly nine years, I have done all the dumping in that time. I have also been told several dozen times by many different women that they never know where they stand with me, that I am always a little distant, or aloof. They say that I am affectionate, but there is always a sense that I could leave them at any point. I would say that these things are all fairly true assessments.

As I thought about Kay it occurred to me that she acts a lot like I usually do. When we're together she's 100% there, and seems very into me. However, I don't hear much from her during the week, and I feel like I am always the one doing the chasing. I suppose this may partially be the reason I am so interested in her, we always want what we can't have.

After talking with Kay on Thursday night I decided that I wasn't going to call, email, or text her over the weekend. We left it that we would get together this week sometime, and I wanted to give her a little space. My normal dating instincts seemed to have worked well in the past, so why change the formula. However, I began to question myself. If my instinct is to send her a text message to say hello, than isn't that what I should do? Is that what I would normally do, or is that just what I want to do because I like this girl more than normal? I suppose it's like the philosophical question "If a tree falls in the forest, does it make a sound?", you can ponder and debate this all day long, but you can never answer the question.

The question now is how long do I wait before I contact her? I am going to try and hold out today and see if she calls me.