Ahh, the plight of  single men.  If we wish to consort with the fairer sex, it’s up to us to approach women, charm them, ask them out, take them out, pay for the entertainment, go for the kiss, try to get to the next base — and risk rejection at every step.  Every time you’re on a date, a cop might as well come up to you and say, “You have the right to screw up.  Everything you say can and will be used against you in a court of public opinion of your date’s girlfriends.” You should probably avoid girls named Miranda.

At the same time, you have agency — you get to ask her out, instead of having to wait for the phone to ring.  This is a good deal.  With a little bit of caution and foresight, you can avoid these dating pitfalls and instead have a lot more fun and success in your love life.  Here’s what to watch out for.

1. The postponed response, or the Almost Yes.

You call her up on Monday to ask her out for Friday night.  She says, “That sounds great — let’s do it!  Except there’s this one thing at work I may have to go to that night, and I won’t know until Wednesday if I’m free Friday night.  Can I call you back on Wednesday or Thursday to let you know?”

Ooh.  This has happened to many a man many a time.  And if she’s some elusive hottie you’re really into, it may seem like you’ve hit the jackpot.  She said yes, right?

Wrong.  She said maybe.  Which basically means you (more…)

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Here’s a letter I got recently from a female Harvard undergrad. Names have been changed to protect the shady:

Dear Ali,

I have a question for you regarding a dating situation I had recently.

Jon had been pursuing me for several months, sending me friendly texts, chatting in our psych class, before I was finally convinced that his intentions were (at least somewhat) honorable. I began spending time with Jon outside of class; we would hang out together at parties on the weekend and sometimes grab lunch during the week. I was aware that Jon was far more available to spend time with me on weekend nights than during the week, but, I figured, we were both busy people.

After a few months of casually hooking up, I decided that I liked Jon, but I didn’t just want a casual relationship with him. Before things went any further, physically that is, I communicated my concern to Jon. I told him that I didn’t just sleep around. If he did not want a commitment, this could not go any further.  Jon understood, and even told me that I was the kind of girl he “respected.” I was satisfied with this response; maybe I had actually found a good guy.

Shortly after Jon and I slept together, he stopped calling me.

I thought I had been so careful. After all that time, how did I still become his one-night stand? I need sage advice — how do I spot a “bad boy” in disguise?

Sara

Wow. Tough one, Sara! Sounds like you were pretty circumspect about this one and still got blindsided.

Before we start, two things: It’s possible for you to do everything right and still get a bad result. It’s called life. The key is to dust yourself off, chalk it up to experience and keep on moving. Do not indulge in self-pity, blame or shame, but do learn from your experience.

Second: Could you have done things differently? This is where the gold nugget of learning resides. I was just reading about one of the greatest game players of all time. His name is Bill Robertie. You’ve probably never heard of him: he’s a champion chess player, a 2-time world backgammon champion (a record), and a poker expert. Nobody in the world has that level of mastery in those three domains.

By his own account, the way he got to be world-class in all three disciplines was to learn from his own mistakes. He would study every move he made, and think: “How can I do this better next time?” And he did. And he got that good.

So the key here is to see what you can and should do differently next time. I don’t have the full account of who Jon is and what transpired between you, so I’ll be talking in terms of principles rather than specifics.

What we’re going to focus on today is not just how to avoid bad boys, but how to ensure that you (more…)

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Dear Dr. Binazir,

Hello! My name is Kevin and I am a senior in college. I have really enjoyed reading your Tao of Dating emails for the last few months. The advice and philosophy you offer is both constructive and life-affirming. Additionally, I am continually impressed by the respect, humility, and humor with which you communicate. In short, thank you!

Right now, I’m in the middle of a difficult situation and I trust that you more than anyone I know might be able to help.

Last spring, I met a girl who has changed my life. I noticed her immediately – she sat in front of me in the Gospel Choir and would frequently look back at me and smile/stare, never saying a word. I knew from her comportment (and the fact that she always brought her biology text to rehearsal) that she was someone with whom I could become close friends, and hopefully more. After weeks, I finally worked up the courage to introduce myself. We became fast friends. Even though we do not share mutual friends (she is a sophomore), we have gone on hikes, runs, and bike rides together. We have a meal together once every other week. This past summer, since she worked in a lab near my house, we had a wonderful picnic on the Charles River.

I am sure that this sounds very straightforward so far, but there is one major complication – she has a boyfriend. He is my age and goes to another school. They met in high school and started dating when he went to college. He and I have met and hung out together a few times, and while we are not going to become close friends, he’s definitely a decent guy. He is in love with her, but to be honest, she seems surprisingly ambivalent toward him. Even more inexplicably, she has never called him a “boyfriend” and never mentions him to me unless he is present. When she told me that he would be joining us one day over the summer, she called him “my apartmentmate.”

Over the spring and summer, things were moving on a very fast, positive trajectory. Now, with only six weeks to go before the end of the academic term, things have slowed – but not for any discernible reason. We had an hourlong breakfast two weeks ago and are planning to do a challenging dayhike with a small group next weekend. Her birthday was Tuesday, so I gave her a card. But it just seems like something is ‘off.’

Her behavior over the last week has been uncharacteristically fickle. One day she was enthusiastic and flirty and the next day she was uncommunicative and tense. In short, she seems conflicted – as if I may be both a source of happiness and confusion. (To think that I may be a cause of anxiety is a terribly frustrating thought!) If time were no object, I would take this as a signal to step back. Moreover, she will be in Spain next term and I will be in Greece for my final term in the spring. Even though we only live an hour apart (Massachusetts to New Hampshire), unless she were to break up with her boyfriend, we will likely not see each other much (if at all) after I graduate. I know that if I do not tell her how I feel soon, I will not have a second chance.

Basically, I am at a novel impasse. I have never attempted to date a girl who was in a relationship before and she is the only girl I have ever met that I would do anything to spend my life with. What should I do?

Thank you again for all your insights and in advance for your advice.

Sincerely, Kevin

First of all, thank you Kevin for your astute observations on the nature of my work.  Constructive! Life-affirming! With gobs of respect, humility, and humor!  I agree.  Especially the part about humility.

Tomfoolery aside — aww man.  Could I write a book on this one.

Oh wait, I did.  It’s called The Tao of Dating for Men.  And I wrote it specifically for the brainy, overthinking, underexperienced dudes who populate the Ivy-type schools that our good man Kevin attends (he’s at Dartmouth).

This letter touches upon many themes that are relevant to the love lives of college boys, so we’re going to blunt-dissect them one-by-one, because that’s the best way to see all the components of folly that’s going on here — and destroy them in the process :)

Why does all of this sound familiar to me? Because I was Kevin not too long ago, all through college and medical school. Man what I would give to have those 8 years of my life turn out differently.

But I digress. Let’s begin with Theme #1:

1. You must get out of the scarcity mentality

This is the big no-no when it comes to college romance.  Let me break it down for you: there will be a time in your life when (more…)

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