The Switch

Mission Number One:

1. Hook up with someone as old as my mom (54) and as young as my sister (20) in a month.

The Hunt
Saturday night turned to Sunday morning with no real advancement on the mission. I went to this upscale Cougar bar with my friend Tracey. She is one of those "friend" girls that you see in movies and you immediately sense that she is attracted to her "boy" friend. And as you watch, you wonder how this guy can be so obtuse as to not realize the attraction. Truth is, most guys aren't. It's just easier to stay friends. And it's nice to have friends that would go down on you in a theater.

Anyway, Tracey volunteered to be my wingwoman for the night. She told me about some company that rents out girls to help guys pick up, and thought she would give it a try. We laid down a few ground rules. The actual age of the women would have to be determined by Tracey. The other rule was that I could not have any sex until I bag the elusive 50+ cougar. Which means, I will get no play until I climb that mountain. Not that big a deal for me under normal circumstances, but knowing you can't have sex is different than just not having it--in a very guy sort of way.

If you're cougar hunting, here are my top five tips:

1. Bring a girl. It made it really easy to make introductions. Especially if she's hot.

2. Find the women by herself. Be wary of hookers, though. Groups of ladies will act crazy in public, but you have a better chance of picking up a waitress in a strip club than bedding one of these convention floosies.

3. Don't use your real name. This is especially true of me (hello, Rob Lowe). I became Rob DiStephano for the night.

4. Don't be a cheapskate. To find the best talent, you need to go to the expensive bars. And make sure you buy her a drink as soon as you exchange hellos.

5. Leave the frat boy at home. Work alone if you don't have a wingwoman. Dress nice and leave Chet and Zane at home to tend to their beer bongs and Playstation II.

My Disenchanted Evening
So, here's a brief recap of the evening. I met four woman, only one was above 50, but she looked 30. She, unfortunately was a hooker. Tracey told me that would be cheating. I then moved on to a group of two (where I learned the second tip). About halfway through the night, I discovered this was not going to be an easy task. Hopefully, part two of this exercise (taking home a 20-year old) would be easier.

Flipping the fifty switch
This is Hollywood, so you find some tasty talent in the 40+ range, whether it comes by God's hand or a plastic surgeons. However, most guys flip the switch off at 50. And let me solemnly declare the pickin's are a bit more slim around the half-century mark.

Damn, I wished my mom had me when she was 16. This would be so much easier. I totally could bang a 45-year-old.

Next weekend, the Century City Mall. Let's see what Cougars do during the day.