My Weekend at Caroline’s

I need some fu-king sleep.

This weekend I hosted at Caroline’s, which was a nice opportunity to get seen and PAID by a New York City comedy club. However, my schedule was a little tough: 1230 am Friday (followed by 230 am prom show), Saturday @1230 am and Sunday at 10 pm. My contacts have not come out of my eyes since Friday. The lesson I have learned: comedy and law are a tough fu-king combination.

Friday’ show went well and then came the prom show. The prom show was important to me because the last time I did a show for college age/college bound kids it was in Minnesota in April and I had one of the worst sets of my life. The prom show gave me a chance to start performing better to that age group. The kids were from Staten Island, which immediately made me think of the psycho groom from MTV’s True Life. Never have I gotten so much mileage out of the phrase, “I will fu-kin’ gut you!” Got home at 4 am and after a refreshing four hour nap I was at the day/weekend job of lawyering.

That night came the worst show of the weekend. A crowd with a lot of ooooos and ahhhhhhs instead of hahas and guffaws. This was also the pimp crowd where much of the crowd decided it was time to wear red and black pimp suits.

After getting a robust 3 1/2 hours sleep Saturday night it was back to lawyering. When I left my office on the way to the club I decided to buy a milkshake from Mr. Softee. And the first thing Mr. Softee said was “Hey I saw you at Caroline’s last night – funny stuff.” My two favorite things, comedic recognition and Mr. Softee milkshakes.

Sunday night’s show was the most entertaining for one real reason. The middle aged Italian guy and his two escorts.

I was not sure they were escorts in the traditional, Eliot Spitzer mold. I thought maybe they were just career-minded New York City women. But as I talked to audience members and friends at the show the consensus seemed to be that they were working girls. Some things impressed me about these women:

1) Their taste in men. They were with one guy (I believe they were going to engage in a threesome after the show) and he was a 5’5″ humorless balding Italian in his late 40s. He probably has something to hide if he is taking these women to a late Sunday show. The old, “My wife kisses my kids with that mouth,” sort of rationale.

2) Their looks. Seeing a 10 in person is rare, but this guy was with two of them. I was informed that their hair and breasts were fake (possibly more), but I just thought they looked like nice people and that is why I thought they were 10s.

3) They were adventurous. As everyone giggled as they left the club it became more exciting when we went upstairs and the two women were posing for videos and photos making out with each other in front of Caroline’s with the Italian Stallion looking on.

A tremendous way to end an exhausting weekend.