7 simple steps to have more mature dating skills than a sixth-grader

There is literally no question more central to existence than “how are you?” — and other painful truths.

Single people of America, I’m sick of watching you mess this up. Allow me to offer simple ways you can fix it.

A caveat: it took me about 10 years of dating somewhere around 100 women — numbers I take no pride in whatsoever — to find myself firmly in a relationship again.

So, I’m clearly a deeply flawed person; and I don’t know what I’m doing any better than the next self-centered member of industrial society.

But, I am in a relationship, so that automatically makes me more clear-headed than you. There is no limit to stupid stuff you’ll do when you’re dating, and did you ever notice how the only sane people you meet are already taken?

Consider me your friend who had to work late, has thus shown up at the bar sober, and who is trying to talk you out of going home with Dracula — as mysterious and handsome as he is.

I’ll probably be drunk again myself tomorrow, and poised to do something equally as foolish. For now, just hear me out.

1. Stop looking for someone who “challenges” you

You hear it all of the time. “I want someone who challenges me.” This is usually code for wanting someone who fits a conventional and unimaginative definition of success — he’s a lawyer, she’s a doctor, he went to such and such Ivy league school; or, someone who can have a 3-hour debate about whether or not it’s politically correct to say a party was “crazy” (lest it minimize mental illness).

In my experience, these qualities should be red flags, rather than beacons. They have no substantive consequence on your long-term enjoyment of a person’s company. Those in the former camp tend to use their pursuit of socially-constructed goals as a shield from the discomfort of introspection, while those in the latter camp are looking for new ways to distract themselves from the present moment. (They’re also not fun at parties.)

If anything, look for someone who challenges you as a human. Someone whose attentiveness and consideration makes you call into question your own self-centered tendencies.

2. Stop having preferences that don’t matter

I was once dating a really great woman. Then I found out she listened to Nickelback. I nearly instantly lost my attraction to her. The common defense for this idiocy is “you can’t control what you’re attracted to,” but now I realize that — in many cases — this is an excuse that absolves you from examining what your preferences say about you. It’s an invitation to extend your prejudices about that one thing, so that they round out your entire perception of that person.

So, he likes country music. So, she used to smoke cigarettes. So, he’s merely half-a-foot taller than you. And now you won’t date that person. That’s a deal-breaker. Is that written in your DNA, or is it the effect upon your own self-perception — or the perception of your friends — that keeps you swiping again and again?

3. “How are you?” Answer the question

I get it, you get lots of annoying and idiotic messages, but “how are you?” should not fall into either of these categories. I don’t know how men generally feel about this question, but I recall seeing many a woman’s Tinder profile demanding that guys have something more interesting to say than “how are you?”

My problem with this is there is literally no question more central to existence than “how are you?” Every action that every person takes throughout their entire day is in pursuit of affecting their answer to this question. The answer to this question is guaranteed to lead to a conversation that is relevant to yourself and your well-being.

That is, if you can bear to suspend your desire for constant distraction, look inward for a moment, and answer the question honestly. Which, I posit, is why it’s such a problem for so many people.

To me, a person asking “how are you?” shows far more potential for emotional intelligence — and is far less histrionic — than someone who inexplicably launches into the equivalent of an opening monologue for Jimmy Kimmel Live.

4. Stop “ghosting”

There’s all sorts of great reasons to “ghost,” wherein you simply stop responding to a person’s messages. People don’t like to hear the truth. They get the message. You’ll somehow hurt them less. These are all lies that we tell ourselves to avoid growing a spine and acknowledging the humanity of the other person.

Not only was I a ghostee many times, I was I also a ghoster, until I learned my lesson. I had a great first date with a woman. She asked when we could see each other again, but we put it off. Eventually, she stopped responding to my texts.

It turned out she had “ghosted” on me. What I mean by that was she actually died. I experienced both the confirmation of that tiny inconsequential thought that sometimes pops into your head when someone ghosts on you (“maybe he died”), and the glaring realization of the humanity of every woman I had ever ghosted on.

I didn’t ghost anymore after that. You are dealing with humans, not e-commerce items.

5. Stop talking too much

I’m lucky. My girlfriend doesn’t speak English. I spent most of our first date — years ago now — struggling with Google Translate on my iPhone. After dating in the U.S., I was was certain that the silences that I interpreted as awkward were soon to be met with the Spanish equivalent of “Nice meeting you. I’ve gotta go.”

What I soon learned is the value of talking less. When you’re communicating in another language, you’re less likely to go off on some pointless tangent about how Spoon will never make another album as good as Girls Can Tell, and how hard it is to determine the perfect point of freshness at which to slice open an avocado.

Instead, you only say the things that are important, and the words don’t have the same baggage associated with them as your native language. The words are taken at face value.

When dating in the U.S., I would often play a game with myself where I’d try to do less talking than the other person. The aim was to ask more questions, and do less rambling. I usually failed.

Sometimes, though, I’d get bowled over with tangents, tirades, and diatribes, as if there was a three-dimensional spreadsheet in my date’s head, with each word setting off another association in six different directions. I could relate, because I often found myself guilty of the same.

The cruel paradox of talking up a storm is that you leave the date being sure it went great. Your date, on the other hand, is thinking he didn’t ask me a single question!

Language is a technology, and it can be every bit as detrimental to communication as an iPhone. (Unless you’re using Google Translate.) Say less.

6. Stop being a flake

I’ve heard in some circles that dates are dead, and that it’s all about last-minute hook-ups. One woman I dated was astonished when I proposed a date, time, and location for us to meet up. So, I run the risk of sounding old-fashioned. Stop being a flake!

For those who have the empathy of a Hyena, let me explain why this is important: When you make plans with a person, what happens is they then turn down other plans. When you cancel on them last-minute, it’s often too late for them to make other plans, or to get in on the plans they passed up.

I get it, they aren’t you, so why should you care? Because people other than yourself sometimes matter.

This, much like “ghosting,” is a bit of an arms race. If everyone is flaking, you eventually learn to hedge your bets. One friend of mine resorted to making arrangements for 2–3 different dates on a given night. Usually, all but one cancelled. Sometimes, they all cancelled. I never resorted to this, but it was a perfectly logical strategy.

Stop the flaking. Listen to Gandhi and be the change you want to see in the world.

7. Do more boring things

America has a huge problem. In comparison with the rest of the world, the number of couples lying on the grass, making out and generally doing nothing is at a dangerous low in America’s parks.

But there’s not much park space in America. Bullshit. Chicago has tons of park space. Go there during the three weeks of the year that the weather isn’t absolute shit. Then go to a park. Not nearly enough people lying in the park and doing nothing.

Call me an introvert, but your significant other is not a doll with the sole purpose of accompanying you at street festivals, half-marathons, and Coachella. If you can’t handle a bit of doing nothing in particular with that person, you’re doomed.

So, there is the hard-earned dating wisdom that I’m completely unqualified to give to you. Fight the paradox of choice, practice accountability, hold hands, gaze eyes, and generally love one another. When someone asks “How are you?” you’ll have an answer you’re glad to share.

Written by

Bestselling author of “Mind Management, Not Time Management” http://kdv.co/mind

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