How A Gross Slob Like Me Met The Love Of His Life


I had no furniture, I was 20 lbs overweight, no job, depleting bank account, owed the IRS, out of shape, I drank every night, I was separated but not divorced, two kids, depressed and maybe suicidal, and finally, I secretly wanted to be a standup comic.

I also didn’t like being alone. I am the sort of person who likes to be married.

In other words, I was gross, unqualified for anything, an alcoholic, and delusional.

Probably paranoid also since I was constantly getting fired from things at that point, despite saving the world economy in my spare time (sadly, I have to refer you to my book for that story, which is a true story).

I had a table and one chair and I had a sofa. I had no plates in my kitchen. I had a mattress on the floor. That was the extent of my furniture. I had some books.

I sat on that one chair and made it a full time job to find the woman of my dreams.

This worked for me. Might not work for anyone else.


I saw some article recently, “how to bang a lot of chicks”. That’s not what I mean by quantity. In fact, that’s the opposite of quantity. If anything, if you follow that strategy you will fail.

But for me, since I had been fired by, CNBC was no longer using me, The Financial Times fired me, two businesses I had started were failing, and there was nothing else for me to do: I had plenty of time to sign up for lots of dating sites and send at least 100 messages a day to women.

I would arrange dates for lunch, dinner, whenever. I’d go 40 miles to go on a date. Some women wanted to talk on the phone. I’d set aside an hour or two a day to talk on the phone.

But nothing really mattered until I met the person.

If you meet ten people you think you are attracted to, you might actually be only attracted to one. The other thing is: given my situation most women didn’t even respond to my messages. So quantity was critical.


If I liked a girl in an elevator, I would ask her out. If you worked in the phone-bill collection store, I asked you out. If I bumped into you in the street five years earlier, I would see if you were still single and ask you out. If you served me an egg sandwich, I asked you out. If I liked you in sixth grade, I would find out if you lived in the Northeast US, was single, and I would ask you out.

Dating is like war. You have to consider every angle, you have to be flexible, you can’t rely on what worked for you in the past, and you have to be very open-minded.

I know this sounds pathetic. I don’t care what people think. This is why I deliberately made this a too-long-to-read status update. Anyway, this is what I did.


I don’t have a lot of masculine (or feminine) mystique. Which means I had to work with what I had.


I put up no picture on any dating site. Making use of my “nothing”.

Someone told me, or I read somewhere (I forget) that mystique is a key part of charisma. I have no idea if this is true.

Most women won’t consider clicking on a profile with no picture. If they did, though, then it meant I could start having a conversation with them and take it to the next level. They had already passed a significant hurdle in clicking on me (a profile with no picture) so they had something invested in me being interesting.

Then, if they said, “why no picture” I had an easy answer which was true “I’M ON TV A LOT”.


Not that anyone is shallow, but they suddenly went from knowing nothing about me to knowing I am the type of guy who could be on TV a lot. And then I would send a picture right away.


My biggest rule: Saying NO when everything seemed great.

If I liked a girl, she was pretty, we went on a date, and it was all systems go, BUT I knew this was not going to be a long-term relationship for whatever reason… then I said “No” and would leave before anything would happen.

A spider can get stuck in it’s own web (uhh, is this true? I have no idea) and I didn’t want to spin anything I would have a hard time getting out of. This is really the most important rule.

Too many people go to bed too quickly. Two problems then:

  • now you have a situation to deal with.
  • if she goes to bed quickly with you, she might go to bed quickly with someone else.

So I liked girls who said “No” also.


Claudia said to me, after our first kiss, “I like to spend [she gave a time period] getting to know a guy.” I said, “Perfect, I like to spend [insert the time she said times two] getting to know the girl.”

This sounds manipulative and even like gamesmanship, and it is. I didn’t want to seem like I was in a rush or anything. But the reality was, I was shy and liked to take it slow. So it was easy for me to say that. And it threw her off a bit. Mission accomplished!


Tea, no dinner.

I was such an idiot, always setting up dinners with women. To be honest, you know in a few seconds if you’re going to be attracted enough to even consider spending the rest of your life with that person.

One time I took an hour long train out to Coney Island for a dinner with a woman who had been the Olympic swimming champion of some Eastern European country. Within two seconds I knew not for me. But there I was in a two hour dinner and then another hour long ride home on a train. No good.

When I met Claudia I pushed really hard for dinner. I knew I liked her. But she kept writing back, “No. Tea! No dinner.”

So we met for tea. And she had a specific timeline. She had a 5pm train to catch. So it had to stop at a certain point no matter what.


I’ve already written this but when Claudia first wrote me that she was from Buenos Aires I wrote back, “Great! I’ve never been to Brazil.” Thankfully she jumped over another hurdle to meet me by ignoring my total stupidity.

Shows you either how useless 18 years of formal education is or how stupid I was. Maybe both.

Other situations: I went on a date with someone interested in Kaballah. I read everything I could about it in a 3 hour period and was able to drop all the right terms and sound impressive. Again, this sounds manipulative and it is but two things:

1. I fully admit I was in a weaker position.

The myth of manipulation is that the manipulator is somehow “stronger” than the person being manipulated.

But no manipulation ever occurs unless the one doing manipulating is weaker. That was me. Weak.

2. I really wanted to see if I could be interested in the other person’s interests. Particularly since at the time I had almost no interests other than surviving, drinking, and meeting someone. Oh, and I wanted to be a standup comic.


I would surprise on every date. Sometimes I would buy offbeat gifts. I also had a list of carefully researched outlandish places all over the city where I could take people on dates. Hidden restaurants, all-dark restaurants, offbeat places that nobody would expect, etc.

Sometimes I would go to the restaurant the day before and pay and tip with all two dollar bills. So when I arrived there the next day with my date I would be treated differently than other customers. I know this is starting to sound more and more loser-ish but I can’t help it. This is what I did. And it worked!


I could care less about the Federal Reserve and the economy of Greece, etc. But three things about economics are very useful in the dating world:

A. Opportunity Cost.

If you waste time with someone you ultimately won’t enjoy being with then that was time you could’ve spend finding the right person for you.

For all you know, that was THE time you would’ve found someone who would’ve changed your life. Opportunity cost in time is a huge factor in dating that 99.9% ignore.

Always remember in life: money you can always make back. Time, once spent, is gone forever.

B. Supply and Demand.

By using many dating sites and opportunities I kept the supply very high.

I couldn’t really control demand that much. I couldn’t really do anything to increase the size of the demographic that likes me.

But I did everything I could to increase supply so my ultimate “cost” (time, stress, loneliness) was as low as possible while my value increased.

C. Statistics.

I had no interest in going for someone who would probably not like me.

And, if someone was a lot younger then chances are I would find them boring anyway. So whether it was right or wrong, I used statistics to weed through opportunities.


I was almost too honest on dates about the things that were both good and bad about me.

But I had given up on wearing masks to get people to like me so figured this would be an important part of not wasting time.

Claudia asked me immediately on our date if I could describe what was up with my separation. I had nothing to hide.


I didn’t like any games at all. If people played games, I was out. For instance, if someone thought it was weird if I called the next day but then was upset if I didn’t call the day after that I felt like some “rule” was being used. This was grounds for immediate disqualification.

If I didn’t understand the rules, then I wasn’t going to follow them.

Similarly, if I couldn’t tell if someone liked me by the third date then it was over. You don’t need to be a psychic to know if someone likes you in that way or not.

This is not to say it was all clinical and choreographed. On our second date I wanted to kiss Claudia. But I was really shy. I could tell she liked me. So we went on a walk. I had a spot in mind overlooking the Brooklyn Bridge from South Street Seaport. But I got scared.

Then we walked another mile or two and it was getting windy. Finally, we got to another spot and I did something embarrassing and stupid. I made fun of her teeth a little (she has tiny fangs on each side) so I could have an excuse to lean in and kiss. And she kissed back.

Later I called my friend, Dan, and told him, “Ok, the search is over.”

Today it’s dark and snowing, like the moon split into a million pieces and fell to the Earth. Claudia hates the cold so next week we go to Florida. Sometimes I’m desperate and scared. But sometimes I’m happy.