How I Met Claudia

I was on one of my first dates after I had separated from my wife and the girl asked straight out what my net worth was within five minutes of sitting down. I had met the girl in an elevator the night before. I was walking into a building to visit another woman. I noticed this girl and I prayed to God that she would enter the elevator with me. She did. She hit floor #9. I hit floor #10.  God is good.

Somewhere around the fourth floor she turned to me and said, “please tell me 2009 is going to be better than 2008”. She was about five feet tall and had thick blonde hair, light blue eyes. I told her it definitely was. 2008 was bad for everyone in every way. It couldn’t get worse. It was horrible for me, I said. I had gotten separated. A month earlier I had been on the floor in a fetal position and then put ads on Craigslist pretending to be a psychic. In my “psychic” capacity I told the future to about 20 different people. And probably tried to hit on ten of them.

I got off the elevator on her floor instead of the tenth floor.  We talked for ten minutes. My phone kept ringing. My friend on the tenth floor (a woman) wanted to know where I was since the doorman had announced my presence about fifteen minutes earlier. Somewhere Between the first and tenth floor I got lost in a maze it would take me two months to exit.

My new friend’s father had died during the year. And her husband, twenty years older, had cheated on her and divorced her that year. She was crying. She asked where I lived. I said, “The Chelsea Hotel”. She said, “I’ve never had sex in the Chelsea Hotel”.

My phone kept ringing while we were talking. “Who is that?” she said. And I said it was a girl who lived on the tenth floor. So I had to go.

The next day I sent her flowers and a teddy bear. I called her and we agreed to go to dinner.

Right away she asked me my net worth, what the specific details of my divorce were going to be, why wasn’t I working, what were my plans for the future, what political party I was a member of,  everything. I told her what I had going on. She was skeptical. She said, “those sorts of things never work out.” She asked me a million questions. I was honest about everything.  She said, “I didn’t think you were a good looking guy last night.” Welcome to New York dating post-marriage.

Her conclusion: “you’re completely insane. I can’t go out with you.” We went out for two months but she broke up with me at least once a week. It was really painful. I didn’t have enough self-confidence to stay broken up. She’d break up with me in the morning and then call me later and say, “lets go out for a drink” and I would drop all other plans to go out with her again. I was drinking non-stop.

During this time, wanted to “rework” my contract, which resulted in me getting fired two years after I sold Stockpickr to them. The Financial Times lost their advertiser for the page I was writing on so they effectively fired me. CNBC no longer needed a bullish guy when the stock market was going down every day so they stopped using me. I let one business fail and started another business that was doomed to fail. I invested in a few other businesses but I had no idea then what would happen to those.

And still I kept getting broken up with at least once a week if not more.

My kids would come over every other weekend but since this girl would break up with me every Friday I had no idea what she was doing on a Saturday night and I’d get anxious about it. I’d arrange for my kids to get their nails done or something and I’d try calling this girl but no pickup.

I stopped returning calls from co-investors and my business partner, Dan, had to explain I was sick or busy, or dealing with divorce, or whatever he did to explain to people. None of my friends wanted to meet this new girl because they were all 100% sure that it would not work out.

I started meeting other girls via dating services to fill in the gaps when the first girl would break up with me. One girl was the host of her own TV show on ABC. Her dog shit on my rug. She wanted me to only wear suits. She wanted my teeth whitened. She wanted my hair cropped close to head (ugh!) “I’ve written a book on dating,” she said, “so you have to have a certain look or else I can’t be seen with you.” “You need to be groomed,” she said. It didn’t work out. Anyone who looks at me can see I can’t be groomed even if I wanted to. And being groomed like a dog is hard work!

Another girl asked me, “how do you deal with all the girls who want you for your millions?” And I was like, “i’m not sure where you’re getting your information from but it’s not what you think.” That didn’t work out. She wrote me a letter at the end (two weeks later), “you have mental problems and should see someone about that.” She was a pyschiatrist so she was an expert. She had said to me a week earlier, “If you use Ikea to buy furniture for your new apartment I’m going to have to break up with you.” She had to break up with me.

Another girl I introduced to some of my friends. People I had been friends with for about ten years. During the evening she got so drunk her breasts kept falling out of her dress and she wouldn’t notice at all. She would keep talking with her breasts fully out of her dress and people at all the other tables looking at us. So I walked her home. On the way back to her place she kept laughing and saying, “your friends really hate you. They only like you because they don’t know who you really are.” I got her into her apartment, dropped her on her bed, and then left and I still think about what she said and wonder if she was right.

I moved into a two bedroom apartment so my kids could visit me. The last time they had visited me in the Chelsea Hotel I saw a used condom on the staircase of the hotel. Not a good environment for kids. The new apartment, right on Wall Street, had a bed for me, two beds for the kids, a couch in the living room, a table but no chairs and no other furniture. The kids and I would keep our clothes on the floor. We’d eat on the floor. We played Monopoly all day long on the floor. By the time they left each weekend the floor was covered with food, games, books, videos, whatever. And a housecleaner would come on Monday and clean up.

Then I’d see my friend again on Mondays and she’d break up with me on Tuesday.

I was exhausted of being broken up with. I was broken.  It was like I had returned from outerspace after a 12 year visit around the planet Mars. But the planet had undergone a nuclear war and everyone was radioactive so I couldn’t touch them. “Isn’t there anyone out there who isn’t radioactive?” I would ask out loud but I had nobody to talk to. My apartment was empty. My day was empty. I’d walk around doing nothing.

I finally decided to take it seriously. No more second dates if  I knew there was no serious relationship. No more drinking. Back to the Daily Practice for the first time in three  years. I defined for myself very clearly what I wanted. I liked being married. I wanted to meet someone I would marry. I’m an ugly guy and had no prospects in life at that moment so not the easiest thing.

It was a fulltime job for me. I spent three or four hours a day writing girls on various dating services. I wanted to meet someone. Finally there was a girl who had an interesting picture who said she was from Buenos Aires. This was on J-Date, a dating site for Jewish people. She was clearly not Jewish. I wrote to her and said she seemed really different. Maybe we could meet for dinner?

She said, “no dinner. Just tea.” I wanted to push for dinner. Maybe something could happen.

“No. Tea!”

She was from Buenos Aires. I wrote and said, “Oh, I’ve always wanted to go to Brazil.”

She wrote back and said, “That’s nice that you want to go to Brazil but Buenos Aires is in Argentina. They speak Portuguese in Brazil.”

We met for tea early in the afternoon one day. She told me she was into yoga and that’s what she mostly thought about. She told me all the benefits she felt yoga had. How it was a spiritual discipline as well a physical one. She told me she would take me to yoga and I laughed and said, “maybe next lifetime“. I told her how when I was a kid I was obsessed with trying to have psychic powers to see naked girls. I told her I had two kids. I told her how depressed I had been in my worst moments years earlier. She told me her stories. We talked for a long time and it was nice.

We took a walk and sat down on a park bench in Tompkins Square Park. We didn’t say anything to each other. We had already run out of topics to talk about. There was nothing but silence until she had to go. But I felt calm. It had been a very long time since I had felt calm. We must have sat like that in silence for about fifteen minutes. It’s hard to sit in silence with someone but it wasn’t hard this time.

Eventually she got up to go. She had to catch a train. While she was walking to the train she told me she was selling her house. I asked her where she was going to move. She said, “maybe the East Village”.

No you aren’t, I thought to myself. You’re going to move to the corner of Wall Street and Broad. Where I live.

In a month from today we’ll have our first year wedding anniversary.


(Claudia has an excellent blog at We are starting work on my next book together. It will be a jointly written book).


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