I am not one of those hip people who gets waved past the velvet rope, right into the VIP entrance of a hot nightclub. Instead, I wait outside for hours with the proletariat.

And once I’m inside and at the bar, I’m terrible at attracting the bartender’s attention. I just stand there, mumbling — apparently to myself — while watching people on both sides get their drink orders taken before me. I’ve never really figured out what I am doing wrong. Perhaps it’s the mumbling?

My brother-in-law Dan is exactly the opposite. It’s like his hand is permanently affixed with one of those stamps you can only see under an ultraviolet light. He always knows the doorman. He used to date the waitress. The bartender is his best friend. He is the essence of bar/lounge/club cool.

A few years back he came into town to visit, and in an attempt to show him how cool I could be, I took him to a great little cigar bar I knew of in Beverly Hills.

I had been there a few times before and had noticed that there was a humidor “behind the humidor” if you know what I mean? If you don’t, I mean that there were real Cuban cigars in that second humidor, which although the best in the world, are also illegal to sell in the United States (thanks a lot JFK).

I had worked up a good rapport with the bar’s owner and was pretty sure that I had become enough of a regular that I would soon be offered “The Cubans.” I primed my brother-in-law, who had never smoked a real Cuban before, and left him with the impression that we were “all dialed in.”

We arrived and took a seat at the bar and the owner recognized me right away. This was a great start to the night and I felt that my “cool” quotient had already started to rise.

He asked us what we wanted to smoke and I told him that I wanted him to pick up out something “special,” while doing my best “wink wink, nudge nudge, say no more” routine.

“I know exactly what you are looking for,” he said, “I’ll be right back.”

He walked towards the humidor, and not wanting to look too anxious, I kept my back to him. As I leaned forward towards Dan I whispered, “Is he going to the humidor behind the humidor?”

“No,” he replied.

Dammit!

He came back with a couple of great cigars, but they weren’t Cubans. I was not sure where to go at this point. I thought I had given all the correct non-verbal cues; that the tone in my voice spelled it all out. But my fantasy of finally being part of the “cool” crowd was fading away fast.

We smoked the cigars and drank our drinks, and Dan suggested we have another round of both.

This was it. This was where I was going to make my stand. All or nothing. Home run or strikeout. Sydney or the bush.

I called the owner over, ordered two more drinks, and then told him “we want the real special cigars. You know ‘los mejores’,” as if using my high school Spanish on him would seal the deal.

I probably looked like I was having an epileptic seizure as I simultaneously motioned with my head, trying to convey the universal signal for “you know, the humidor behind the humidor.”

“Ah ha. Got it! Back in a second,” he said.

“Is he going to the humidor behind the humidor?” I feebly asked my brother-in-law, the last bit of my hip quotient hanging on life support.

“No,” Dan replied.

I was crushed. I did not get it. I would never get it. What did I need to do to get this to happen?

When he returned with two more non-Cuban cigars I thought there was no choice but to accept my fate and just smoke the ones he gave us. As I was just about to reach for one of them, my brother-in-law leaned forward and said to the owner…

“We want the Cubans!”

We want the Cubans? Did I hear that right?

I was shocked. I was mortified. You can’t just blatantly say something like that! You need to be subtle. You need to be smooth. You need to be strategic and analyze the situation, waiting for the right time to….

“Ooooh?” said the owner, “You want the Cubans? Hold on, I’ll be right back.”

I was 42 years old, and in that moment I instantly understood that I had spent a large part of my life in the “analysis” mode instead of the “action” mode.

Looking back, I realized how bad it had been at times?

Let’s rewind a couple of decades. I’m nineteen years old and my best friend and I are going over to his girlfriend’s mother’s house. She is gone for the weekend, and his girlfriend has two of her friends spending the night.

Schwing!

I am told one of the girls, Vicki, is a model who has been in jail.

Double schwing!

We get to the house and start to party. Everybody is hanging out in back by the pool, drinking Corona’s, and getting loose. After a while one of the girls says she is tired and is going to bed, followed quickly by my friend and his girlfriend. That just leaves just me and Vicki.

Vicki wants to get in the hot tub, but “oh no,” neither one of us has brought a bathing suit. ”Let’s just skinny dip,” she suggests. At this point I can actually hear a cheesy porn soundtrack start to play in my head….

Bump chicka-bump buuuump bump ba, bump chicka-bump buuuuump bump ba…

In one seamless and fluid motion she strips her clothes off, grabs her beer, lights up a clove cigarette, and slinks down into the hot tub.

Now stay with me here. I am sitting in a hot tub, naked, alone with “hot-model-ex-con-chick,” who is drinking a beer, and smoking a clove cigarette……

A CLOVE CIGARETTE FOR GOD’S SAKE…!!!

And at that exact moment, the thought running through my head was….

“I’ve got to figure out the right time to try and kiss her.”