The Ultimate Cheat Sheet To Online Dating


Note: you may inadvertently also learn everything you need to know to run a business from this post).

I wanted to kiss her before we met. Honestly, I wanted to know what she would taste like. I have no shame about it. I wanted her.

Girls have read books like “The Rules” and guys have “The Game.”

In between “rules” and “game” is this wide river of fear where strangers often die swimming for intimacy.

Recently I spoke on my podcast with Paul Oyer who wrote, “Everything I learned about Economics I Learned from Online Dating.” He’s a professor of economics at Stanford who happens to be single.

I like my podcast with Paul because I mostly like the sound of my own voice while lecturing a professor of Stanford. I made him laugh a few times.

But I’m not sure his book had a lot of good advice about online dating (it did, actually, have good advice about the job market, which he compares to online dating).

For instance, one of the things he has pulled from various surveys on online daters is that men are looking for women just based on looks (they may find other things they like later but looks come first). And women are looking for both looks and money.

So he suggests that guys need to signal that they have a lot of money. One way they can do that, he suggests, is to take out money at the table (make sure it is enough money) and burn it.

Ok, he sort of suggests that tongue in cheek but I can say flat out that won’t work. If anything, it signals that you can lose all of your money.

When I was talking to Tucker Max on my podcast he suggested something different based on scientific studies: wear leather shoes.

Ok, this seems smarter. Women notice shoes. Guys DO NOT notice purses but girls notice shoes.

But forget all of that for a second. Because what I am going to describe below to you is the REAL economics of online dating, my style.

If you follow MY RULES, then you will meet a girl or a guy. OR YOUR MONEY BACK! I have never made that kind of offer before in a post.

Note, I took Economics 101. And then I took a course on economics and statistics which showed that all statistics is a lie.

I took other economics courses but I cheated on all of them. There were two tests a semester and my girlfriend at the time simply let me cheat off all of her tests. BAM! And that’s how you get a college degree. (So if you don’t care at all about dating, then you can call this “the ultimate cheat sheet for getting a college degree”).

And then I lived in the real world – where everything is a lie, everything is a transaction, a negotiation, a sale, with kindness the thread that interweaves through all good transactions.

The REAL economics of online dating.

A) Opportunity Cost: Never agree to dinner.

My guess is either the man or the woman know within a minute if they like the other person or not. In rare cases a person is on the fence but what I am about to suggest won’t detract from that.

When I first started online dating I would go anywhere for any amount of time to go on the date. It’s because I was insecure so I would do whatever it took to get EVERY girl to like me.

This is the wrong approach. You have to assume some will like you and some won’t and you’ll like some and you won’t like some.

If you have to travel far (takes time) and then do a dinner (takes time) and then travel home (takes time) and then do followups, etc then you just took six or seven hours to make a decision that should’ve taken only two minutes.

During those six or seven hours you could’ve met many other people or sent messages to many other online profiles or even attended a salsa class where you would’ve, guaranteed, touched and danced with ten other single women.

You will NEVER EVER get that time back. THAT is opportunity cost. And after you spend too much of it, you’ve lost all of your opportunity and you’re dead.

When I first sent an online message to the profile of one Claudia Azula she REFUSED to meet me for dinner.

I honestly thought if I had dinner with her then “anything” could happen so I really pressed for it.

“No,” she said. “Tea.”

So I took her for tea. Then we went for a walk. Then by 5pm she was on the subway looking for a train. I had no clue whether she liked me or not. It was just a tea.

Opportunity cost is all about failing quickly. The only way to succeed at a business, at a relationship, at online dating, at writing a book, is to fail quickly.

Remember those two words with everything you try in life: FAIL. QUICKLY.

You only get to fail quickly when you don’t invest all of your resources in one “investment”.

For instance, if you put all of your money in one stock and it fails then you just lost all of your money. If you put it in many stocks and traded out of them when they started going against you, you don’t lose much and you live to fight another day.

Living to have many fights is, well, a life worth living.

This seems crude, treating a date like a stock. I’m not doing that. Just explaining opportunity cost.

Your life is precious. There is nothing better in life than being you. So don’t squander the resources of you on things that will not work out for you.


B) Supply & Demand:

Despite the fact that people have PhDs in economics you really only need to know three things to know more than anyone about economics.

a. Too much opportunity cost is bad.

b. Value goes up when either supply goes down or demand goes up.

c. Basic statistics, as long as you understand that 99% of statistics is lying.

There is NOTHING else you need to know about economics to be an expert.

Always assume DEMAND for you is constant.

The only way demand for you goes up is if suddenly you get a lot more good looking or if you suddenly get famous or publicly wealthy.

Else, demand for you won’t change. (Some aspects of demand change slowly over time, as a man gets older and as a woman gets older but that is slow and can’t be acted on).

Again, I have to qualify. This is not a statement about anyone’s shallowness. This is just the way the world works when there are lots of choices and you need methods to weed through your choices.

But value goes up when either demand goes up or supply goes down.

Since your demand is at a constant level, the ONLY way your value can go up (increasing your chances of meeting an online match) is you have to make your supply go up.

There are two ways to make your supply go up.

  1. You send an ENORMOUS number of messages to people who have their profiles online and you use as many dating websites as possible.
  2. You are in a location where there are fewer people of your sexual bias online. #2 is harder to do (it’s hard to know). If you are a single Jewish man in your 40s with a decent job then I recommend NYC. Else, I have no clue. But it should be possible to figure out.

Even if you figure it out though, you probably won’t move.

So focus on #1. If you do at least three hours a day of messages then you are probably doing a good job at increasing your supply online and then increasing your chances.

Note: my goal was to meet someone I could fall in love with, marry, and spend the rest of my life with.

But I think the same rules apply (this is basic economics) if you are just looking to have sex with someone.

C) The Nigerian 419 Scam.

A Nigerian 419 Scam usually starts off with “I’m the son of the ex PRINCE and we seek good partner to send USD 12,500,000 WHILE prince in PRISON!! Please send info IF youare a good partner.”

I recently interviewed Stephen Dubner of Freakonomics fame for my podcast in anticipation of his upcoming book, “Think Like a Freak”. More on that in another post.

But in the book he describes why the Nigerian Sales Letter is so obviously a scam. Why it has grammar and spelling mistakes and most people know instantly it’s a scam.

They do it that was ON PURPOSE. And you can use this technique in online dating.

Whoever responds to the letter has qualified themselves as a total idiot who is ready to be scammed.

So now the Nigerians on the other side don’t have to waste time pursuing people who are not going to be interested (remember: opportunity cost).

There are many examples of this in marketing and copywriting but the Nigerian 419 Scam can be applied to online dating.

Note: they are looking for people who were gullible. I was looking for women who would like me. Perhaps that is the same thing but I hope not.

I did not put a photo on my profile. Many reasonable women will automatically eliminate a guy who has no photo on his profile.

But if someone took the time to contact me back then I would be able to write back with two things: A link to my photo and the reason why I didn’t have a photo up (“I’m on TV a lot and didn’t want to be recognized”)

Now I’ve gotten through several hurdles: they were interested enough to contact me despite me not having a photo (so they liked other aspects of my profile without knowing my looks), they then get my “signal” that I do something interesting professionally.

If they then respond, then 100% of the women who responded agreed to go on a date.

Even though I had the two worst possible things you can have on a profile. No photo and I was “separated”.

“Separated” is a horrible thing on an online profile. For one thing, it means you’re married. I will tell you: single women should not go out with married men. 99% chance it won’t work out.

One time I spent an hour filling out a profile on eHarmony. At the end, the “Submit” button, they kindly informed me at the last minute that their statistics show that relationships with Separated men do not normally work out.

They actually would not let me join at that point. They didn’t care that I had just spent an hour filling out a form. If I knew too quickly what their plan was then maybe they would be afraid the customer would lie. I don’t know. I was pretty upset about it.

But, you can say, if someone “qualifies” themselves in the manner described above then maybe they are desperate. For instance, the Nigerians are desperate for people who are gullible so they set up their letter to force gullible people to qualify themselves.

That’s ok. I was the one who initiated first contact so I can see (note what men use to first qualify a woman) that they look good and have an interesting profile. So after that I just want to make sure that I don’t waste time (opportunity cost) pursuing people who have no interest.

I miss out on the women who would’ve written to me just based on my photo but that’s ok.

I don’t think my photo would stand out in any way and I really didn’t want to be recognized anyway. I don’t think my supply would’ve gone up in any recognizable way.

The only way I would put up my photo is if I could’ve used it to increase demand for me, like if I had drastically improved my looks in some way. This WAS not the case.


I don’t know if this is economics or just basic business. But trust takes part in business in several ways.

One time I was talking to a guy who bought a chain of 40 pizza stores. He told me they were all underperforming (they were Dominos franchises) and were about to go bankrupt so he bought them cheap.

I asked how a Dominos pizza store could underperform. It seems easy to me: solid brand, make pizza, deliver.

“Simple,” he said. “One, you don’t deliver a pizza that looks like a circle. These guys were messing up and delivering pizza of weird shapes. Two, they were not delivering on time. They’d say 30 minutes and then show up on 40 minutes. All they had to do was deliver when they said they would and they would be fine. Oh, and make circular pizzas.”

So he took the 40 stores over and made millions doing just those two things.

It’s the same in online dating. You build trust in various ways:

  • show up on time.
  • make sure you look like your photo
  • don’t lie about your age or anything else in your profile. You can say your homeless but don’t say you have a great apartment and then turn out to be homeless.
  • after the first date, follow up. This is just basic customer service (again, I hate to say this is like a business transaction but the rules are the same).

I would bet the single cause of most bad first dates is that one side or the other lied about their age. Even lying about one year is enough to kill a date.

E) A/B Test the Online Profile.

Most people think the critical factor in online dating is writing the profile. But Im making it the fifth most important thing.

My 15 year old daughter asked me awhile ago why “Creative Writing” is an important class to take.

I told her it was the ONLY class in high school worth taking. She’s taken Spanish for three years and can’t speak a word of Spanish. She’s taken Science, History, blah blah blah and none of it she remembers.

When I give talks (and I know I’ve written about it before) and ask people when Charlemagne, the greatest emperor in European history, was born, NOBODY gets it right within 500 years. Despite the fact that we relearn it almost every year of high school.

In fact, I even got it wrong when I put it in my last book and I’ve looked it up at least 20 times. And if you ask me this second, I probably can’t get it right within 100 years (I think I can get it right within 500). I’m going to say 800 AD. Most people in my talks say 1300 AD.

But creative writing is different. Even if you don’t write books, our entire method of world unification is now done through writing: twitter updates, facebook updates, emails, proposals, sales letters, and so on.

Your online profile is no different. You will get better with practice and if you provide good writing techniques and if you make people laugh.

But the good thing is: if there is enough supply then you can do these two rules:

  1. Be as authentic as possible. Try to define yourself as accurately as possible in a unique way. This is where good writing skills come in and it requires a lot of practice. There are no tricks because if there was a trick then you wouldn’t be unique any more.
  2. A/B test. Like any marketing campaign (and you are marketing yourself, whether you like thinking of it that way or not). Try different profiles out on different sites and see what generates the biggest response.

Define yourself by your favorite comedians. Or your favorite shows. List the most obscure places you’ve visited (this can signal not only money but a sense of adventure).

An A/B test is when you put up two profiles to the same audience and see what people click on. Set up two profiles on a site and start testing. And read “bird by bird” by Anne Lamott to get a little better at writing.

F) The Actual Date.

Always tell the truth.

Pay the bill if you’re a guy. I don’t care what the society says.

Be funny. I would watch standup comedy before every date. At that time (2009) I was watching a lot of comedy that had Michael Cera in it.

DO NOT ‘NEG’. There’s this theory that if you ‘neg’ a girl (say something casually negative about her) then it will throw her off her guard and she will respond by trying to please you.

This only works if you want to spend your life with a woman who responds positively to being insulted. This technique does not work for me.

On my date with Claudia we had one moment that could’ve been awkward.

We took a walk after the tea that she insisted on.

We went to Tompkins Square Park and sat down on a bench and then something happened.

We had nothing to say to each other. There was just silence.

We watched the people walk by, we listened to the conversations of others, and then in about ten or fifteen minutes she got up and said, “I have to go” and I walked her to the subway and shook her hand “good bye”. (Why kiss and create another awkward moment?)

I don’t know what it was, but it was nice to know we were comfortable being silent with each other. Was it a bad sign? I don’t know. We haven’t stopped talking to each other since. Sometime I think I talk too much. I hope she still likes me.

Six months later we went back to that same tea shop and I asked her to marry me. So I guess online dating works.

  • if you have any other suggestions, please put them in the comments. I am DYING to hear.
  • if you met your partner via online dating, please tag him or her in the comments. I want to see how often online dating works.
  • if you know someone who is trying to do online dating, please tag him or her. I want to know if these ideas will work for the person.

Why is online dating so powerful?

First kisses are magic.