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Death and Taxes

The Best Pick Up Line of All Time

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This article was originally published in Death and Taxes on August 30, 2013.

There’s not much douchier by nature than a pickup line. A quick Google search for “best pick up lines” will turn up a slew of the most embarrassing failures of wit you’ve ever seen, running the gamut from insanely crude to insanely corny and everywhere in between. I’m convinced there’s no way to approach a stranger with a canned line without looking like a complete asshole.

But of all the ice-breakers out there, there’s one that I’m fascinated by for its incredibly high rate of success. Deceptive in its simplicity, there’s something psychologically fascinating about how well it draws an answer in the affirmative. It works so well, in fact, it seems to indicate something fundamental about our nature. That line is, simply:

“Can I ask you a question?”

I was out with a friend once when he posed that the question, “Can I ask you a question?” is the single best pickup line of all time. Of course, the trick is that it’s not really a pickup line, per se, it’s a wedge. It requires that you then say or ask something that has some intrinsic worth. Whatever comes next is on you—but asking this question to anyone, in any scenario, almost always gets a, “Sure.” It’s just a knee-jerk reaction. You say yes before you can even think about it.

My friend has a theory about the power of this question: He thinks that everyone wants his or her opinion validated and that the question is an invitation to speak and to have one’s opinion taken seriously—that having one’s opinion solicited is the highest form of flattery.

Personally I think there’s another factor, which is that humans are hard-wired to want to help each other. It’s corny, I know. But there is something to it. I once read a book on management (also corny, I know) that cited some study that found the most effective way to start a sentence when you need to get someone to do something you want is to say “I need ___,” because humans have an innate tendency to provide help when needed.

It was the latter that I found myself thinking about when I noticed “Can I ask you a question” coming up in an even more depressing context than a pickup in a bar: The subway. Living in New York City, you get approached by the homeless a lot. One day a guy I’m still not sure was homeless or more of a hustler approached me and I decided to flip the script:

“Can I ask you a question?”
“What do you mean ‘no’? I can’t ask you a question?”
“Nope, sorry.”

He walked away, looking back once over his shoulder. I felt like a huge dick. But it was interesting. I could see that in this guy’s experience, of all the times he’d asked, “Can I ask you a question?” I might have been the only person to ever just respond, “No.” No one ever says no. When someone asks you that question, it’s like you have a duty to hear them out. Saying no just feels unnatural. To both parties. It’s crazy.

Whether it says something good about humanity or something shitty, I don’t know. But if you ask another human, “Can I ask you a question?” they will almost 100% of the time say yes and engage in conversation with you.

So do with that what you will. Like I said, whatever happens next is on you.

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