My Dating Techniques in 1996

I had no confidence to get girls. Since the age of 12, the girls I most coveted would tell me I was ugly. I always tell my daughters if you want to succeed at something you have to lose at least 1000 times first. So if you want to get good at tennis, be prepared to lose thousands of times, study your losses, think about your weak spots, and then practice every day working on them.  If you want to get good at chess, lose 10,000 times and study only your losses. Your wins will tell you nothing.

I was rejected by women thousands of times. So I had to study. For me, finding a girlfriend, and then finding a wife (or two) was a full time job. I had nothing going for me. I looked too crazy, never had a great job (at first), and wasn’t really the best conversationalist (unless you liked comic books, chess, contemporary fiction, computer programming and that’s about it).

So I had to get better. I took a job at HBO. Cool job. Check! I was a computer programmer there but on my voicemail I said, “this is James Altucher, at HBO.” So nobody would have to know I was a computer programmer.

I moved into the Chelsea Hotel on 23rd Street. The hotel was made famous, in part, by the movie “Sid Killed Nancy” and  then later by the movie “I shot Andy Warhol”. Dylan Thomas died drunk in the lobby. Arthur C Clarke wrote “2001: A Space Oddysey” while living there. There was art on every wall because people often paid their rent with bad artwork (none of the artwork is that good, trust me).

(Sid and Nancy at the Chelsea Hotel)

The woman who lived in my room before me had neither artwork or money. Stanley Bard from downstairs once called up and said, “you’re two months late on the rent.” She said, “ok, I’ll be right down” and she made a running jump out the window and landed on the middle of 23rd Street. My room was on the 9th floor. They cleared out all of her belongings in less than a few hours. And I moved in. All of the walls, even in the bathroom, were painted black.  Cool place to live. Check!

Before a date I’d go to the same restaurant many times and made sure I tipped everyone. So all the waitresses would know me. And they’d laugh at my jokes. I was a bit pathetic. But when you’re on a date and all the pretty waitresses around you are taking care of you and laughing at your jokes then you seem a little special.

I got myself one thousand $2 bills. And I’d carry around these huge wads of 2 dollar bills. When I played chess in Washington Square Park we’d all gamble. Pretty soon the entire economy of Washington Square Park was being conducted in my personal stimulus of $2 bills. The $2 bills would spread from the chess tables to the hot dog stands to the drug dealers and prostitutes. Crackheads were buying hookers for $2 bills. Or vice versa.

(I love $2 bills)

So on a date, when it came to pay, I’d pull out this huge wad of money. First the shock value at seeing that thick a wad of money. Then the shock value of it being all two dollar bills. Who the hell was this guy with the two dollar bills?

Then I had to go. I always had to go. I had a job. I was doing this “3am”project for HBO. I’ll call you tomorrow. Because its 3 in the morning and I have things to do.

A date, for me, was performance art. Carefully planned in advance. Nothing was left to chance. The owner of the restaurant would come to my table and shake my hand: “its an honor to have you here.” A TV show would be mentioned. “I did the website for that show.” A famous actress would be discussed. “She’s my next door neighbor and there’s a line of drug addicts coming out of her door all day and night. “

Then the laughter of waitresses. Then, the $2 bills. Then… I have to go. Its getting late and its time for me to go.

I have to save the world.

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