Her name was Emma. She was also 19, with an irresistible English accent and very cute to boot. I was pretty sure that I was going to marry her.

Except that she dumped me, pulverizing my heart into nanoparticles. It was the only time in my life that I got depressed: poor sleep, suppressed appetite, lotsa Kafka. It kinda sucked.

The next kiss didn’t come for another 4 years, when I was in medical school. That’s also when my career as a professional virgin came to an end. To understate things, I was a late bloomer in the realm of romance.

I wasn’t stupid or ugly. No hermit, either – knew most people on campus. No, I was just clueless.

Turns out that the skill set required to navigate the tricky waters of romantic interaction wasn’t in any book I had read or any class I had taken. Mom, dad, the sex-ed teacher – none of them had taught me any of this stuff.

This is a serious omission, since our relationships with others are the biggest determinants of happiness in our lives. And it wouldn’t be a stretch to say that most people’s lives revolve around their primary love relationship.

So towards the end of med school, I started to read some pertinent books and hanging out with guys savvier than me in this dating realm. Slowly, I caught on that everything I knew about dating and women was wrong.

A few years later, right about when I was a pre-med advisor to Harvard undergraduates, I noticed that my friends and advisees were in a similar pickle. Here were smart, funny, good-looking guys surrounded by single women who were dying to be asked out – and not a whole lot was happening.

See, I like smart people. Smart people created nearly everything that I value – Beethoven’s late string quartets, my HP laser printer, Feynman’s lectures, Four Quartets, and Zippy (my Prius*). I like to see smart people succeed — even created a blog for smart people.

That’s why I wrote The Tao of Dating for Men. Why should anyone suffer like I did? Clues cure cluelessness, so I provided some clues for the smart boys.

But the big reason why this is important is that I’ve seen entire lives derailed by romantic maladroitness.

I was pretty lucky to bounce back after a couple of months.  Other friends weren’t so fortunate.

One of them, Victor, who is my age, is a superbly gifted man – equally talented in both literary and scientific realms.  Since the bastard was smarter than me, I predicted he would go on to do great things.

He fell in love with the tall, blonde and comely Kristin in his sophomore year.  The tumultuous relationship turned out to be his undoing.  He ended up flunking out of his classes (really hard to do at Harvard – trust me) and being asked to take a leave of absence.

He’s doing okay now, happily ensconced in a stimulating career and engaged to a woman he loves.  However, I can’t help but think how things would have turned out differently had his brilliant academic career not been derailed by romantic woes.  Could he have been a world-class physicist, a literature professor, a top-notch entrepreneur, a Nobel contender?  Who knows.

Another example is Mariana, currently a junior at Harvard (yes, she’s a girl, but the story still applies).  She had one of the most impressive high school resumes going into college, having aced 20 Advanced Placement (AP) exams.  For those of you a bit removed from the rubrics of high school achievement, just know that it’s kind of a big deal.

Once again, I predicted great things for her.  And once again, a romance gone awry felled a rising star.  After her breakup, Mariana flunked out of her classes and was asked to take a leave of absence.  She’s back in the saddle again, and at the age of 20, she has most of her life ahead of her.

So this goes out to all my boys out there at places like Harvard, Princeton, Yale, Stanford, MIT, Columbia, Duke, Swarthmore, Penn, Cornell, Berkeley, Brown, Dartmouth, Oxford, and Cambridge. To all you who work at the likes of Google, Amazon, Microsoft, D.E. Shaw, McKinsey — all the geeks, nerds, grad students, techies, hackers, engineers and gadgeteers. It goes out to all the 20-year old virgins, the still-unmarried 45-year olds, and the already-divorced 30-year olds who don’t know what hit them.

I’ve seen a lot of preventable train wrecks out there, so let’s make sure the right information gets to people at the right time.  If there were a dating bible for the smart man, these would be its commandments:

1. Don’t just wait to get lucky – make stuff happen.

As a teenager, I always wondered, when would it happen for me? When would some beautiful girl walk off the pages of Maxim, take me by the hand, look deep into my eyes, appreciate all my wonderful quirks and make out with me torridly?

Wake up, buddy. You create your own luck. If you like a girl, talk to her and ask her out. You don’t expect to ace an exam just by getting lucky, do you? So step up and put in some elbow grease.

As a man, on the dance floor of romance, your job is to lead.  So advancing the interaction isn’t just a good idea — it’s your duty.  Which brings us to…

2. Have a spine.

Wimpiness may be the root of all the dating woes of smart men. I can’t tell you in how many pernicious ways this manifests in the love lives of men.  The deadliest part is that if you don’t work on having that spine and end up with a woman anyway, it’s a setup for failure downstream.  She’ll either own you or get tired of the spinelessness and leave.

So quit being chicken already. Ask her out (again). Set up the whole date: where, when, how, and in what outfit. Don’t be afraid to ask for what you want or to get righteously indignant when warranted. Have strong boundaries. Worry less about offending people, more about having fun.  Oh, and learn how to say ‘no’.

3. Be comfortable in your own skin.

You’re a science geek? Fine. You love computers, baseball cards, classical music, anime? Fine. You’re a horny little devil? Fine. Own it! Quit fighting yourself.

People only love us for who you are, not who we pretend to be.  So that nonchalant facade you’re carrying around, the show you put on, all your efforts to fit in — chuck ‘em.  Because even if the ploy works and you end up with someone, eventually she’ll catch on to the real you.  And if the store is different from the storefront, she’ll walk, and you lose anyway.

I know it’s fashionable amidst the smart set to be dissatisfied with yourself and to keep striving for more, bigger, best.  Hey, I’m all for growth.  However, women will tell you that there’s nothing more attractive in a man than self-acceptance (which is not the same as complacency). So start where you are, and keep on growing. When you accept yourself, the world accepts you.

4. Accept the nonlinearity of women and romance.

As guys, a lot of what we did in physics and math class was to try to straighten crooked stuff out. Model it with an equation. Do a linear regression. Simplify variables. Round things off.

But you know what? They were all approximations anyway. And most things in life don’t follow linear equations – not your breath, not your heartbeat, not your Apple stock, and most certainly not women and romance. It’s nonlinear! It’s chaotic! It’s crazy!

So don’t come and tell me that women don’t make sense to you.  That’s a bit like saying water is wet.  Unlike thermodynamics, women are not intuitively obvious**. Sometimes she’ll come to you when you ignore her and leave when you declare your undying love – deal with it. Women have curves — that’s why we like ‘em. Love is paradoxical and counterintuitive. Realize that and work with it, not against it.

That’s the essence of Taoist thought: observing the world as it is, instead of wishing it to be as we want it.

5. Quit trying to buy your way into a woman’s favor.

This is how it works in the movies: the man does nice things for the lady – buys her dinner, presents – and the lady likes him in return.  It may also be how your mom told you to court a lady.

Newsflash: life is not a movie. And I’m guessing your mom never courted a lady successfully.  Of the two dozen reasons I can think for why this protocol sucks, here’s one: you’re trying to bribe her into liking you. And bribes don’t work! They’re given before the desired behavior has ever happened, so she has no incentive to like you. In fact, many times it has the opposite effect: “Why is this guy kissing my ass when he doesn’t even know me?”

In neurological terms, you want to give a positive reinforcer – like a present – after someone exhibits a desirable behavior. That increases the frequency of that behavior in the future. When you give the positive reinforcer before the desirable behavior, you reinforce nothing. So you’re increasing the likelihood of getting – nothing.

Here’s a second reason: the subtext of your action is that somehow your company isn’t enough, and you need to sweeten the deal with something else.  What if you were so cool, so fun to be around, such an uplifting presence that women would be willing to treat you and buy you stuff?  Wouldn’t that be an interesting world to inhabit?  Chew on that.

6. Quit thinking girls should like you because you’re smart.

A smart guy values smarts above all – and thinks the rest of the world does, too. So he’s bewildered when the jock/frat boy gets the girl and he does not. But those lugs probably think Hubble is some kind of gum and Perl scripts are oyster recipes! How could she possibly choose them over him?

Well, it just doesn’t work that way, buddy. A woman will like you based on how you you make her feel. So make her feel stuff – preferably good stuff. That’s the essence of it. Write that down, engrave it on a plaque, tattoo it on your forehead backwards so you’ll read it every time you brush your teeth in the morning. It’s like, axiomatic, dude.

How do you make women feel good stuff?  I wrote a whole chapter on that, but in brief: be compelling.  When you’re compelling, people have no choice but to respond to you.  My five favorite ways of being compelling:

1. Be a little mysterious. Leave some missing information to be discovered.
2. Be excellent. Do something exceptionally well.  The movie The Tao of Steve is all about this.
3. Give her your undivided attention. It’s a rare thing nowadays, so it’s powerful when you do it.
4. Be outlandish. A little crazy without lapsing into clownhood is good.
5. Be fun. Bring the awesome.  Be the party.

7. Go get rejected – a lot.

Smart people are used to success, not failure. So they’re reluctant to risk social rejection. They’re also frankly terrified of it, then rationalize that it’s just not all that important to be socially successful. A wise man once said, “People either play to win, or play to remain in their comfort zones while maintaining moral superiority.”

So if you’re not getting rejected, that means you’re not out exposing yourself to opportunity. You’re also not exposing yourself to danger, the crucible in which manhood gets forged. So be a man – get out there and get turned down.

Everything you want is outside of your comfort zone. Complacency never impelled anyone to greatness. So if you’re breaching your comfort zone early and often, you’re condemning yourself to a life of mediocrity and dissatisfaction.

Here’s the bright side of putting yourself out there: even if your success rate’s a measly 10%, after asking a mere 10 women out, you’ll have yourself a date. Fortune favors the bold.

8. Allow yourself to be pursued a little.

Evolution decrees that in the Homo sapiens sapiens mating dance, the male pursues and the female is pursued. Fine. But let up every once in a while. Just like water flows downhill and electrons go from high to low potential, there is also an attraction gradient. So be less interested in her than she is in you, or at least pretend you are, so she has a chance to move towards you.

9. Get good by practicing.

Like playing the violin or writing code, success in dating and romance is a skill: you get better at it the more you practice. It’s not some kind of god-given talent that you’re either born with or without. So seek out some good dating resources and put in the same amount of zealous effort that you’ve put into your achievements all your life, and you will be rewarded.

I’m restarting the new & improved version of my super-elite commando Metamorphosis training program for men starting Tuesday 16 Feb.  The free preview call is tomorrow, Tue 9 Feb at 5pm.  Sign up here to get on the call — if your love life has been in a slump as of late, it’s going to be a pretty good kick to the rear.

* Despite all the hoopla, just wanted to say that my Prius still rocks

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Lisa-
Great story!  Now, this is the question you have to ask yourself: “Is this sustainable for another 6mos?  Another year?  Another 5 years? Is this how I want to feel and how i want to be treated?”

If the answer is yes, then carry on.  If not, then that means you have to break up eventually, and sooner may be better than later.  You can do it deliberately with a clear head, or you can wait for nasty circumstances to do it for you (another incriminating text, finding him in bed with someone).  I vote for the former option.

Remember that fulfillment is a feeling, not a person.  Suspicion and mistrust, which is a lot of what you’re experiencing, don’t sound like fulfillment to me.

As for saying that you ‘love’ him: that may be true, but you have a duty to yourself and to the world to love yourself first.  Being with someone who doesn’t value you and isn’t a catalyst for your flourishing into the best possible version of you, is not being loving to yourself.  That always comes first — I don’t want to hear any of this Whitney Houston martyr complex nonsense.

Two other things:

You already know what he said to his friend is not ‘just guy talk.’  If you’re with a man who’s reasonably charming and experienced with women, unless he has stated explicitly that you are exclusive together, you should assume you are not.  With the pre-existing trust issues you’re talking about, it’s a safe assumption that he’s pursuing other options.  It may not be what you want to hear, but it is the way things are.

And you should not be messing around with his phone.  I would consider that a massive violation of privacy, and he probably does, too.  That one’s on you.  However, if things were going well, you wouldn’t be snooping around anyway, so it’s a symptom of a much bigger trust issue.

Fulfillment is a feeling, not a person is one of the big themes of The Tao of Dating: The Smart Woman’s Guide to Being Absolutely Irresistible.  If you want to find the fulfillment that you truly deserve, you need to read the book already.