Single City Guy

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.”

“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