True Love Doesn’t Start With “Hell Yes or No” And That’s A Good Thing

Corey McComb
4 min readOct 28, 2022
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Chances are you’ve heard the decision-making framework of, “Hell Yes, No.” Coined by Derek Sivers and championed into the mainstream by Tim Ferriss and Mark Manson, it’s a filter for deciding how to spend time and energy.

Here’s how it goes: When opportunity knocks, if you don’t feel fireworks of Yes, its “thank you but no thank you.”

“Every event you get invited to. Every request to start a new project. If you’re not saying “HELL YEAH!” about it, say “no.” -Derek Sivers

Running things through a Hell Yes or No filter might be useful for those inundated with endless requests and opportunity. But more and more often, I hear people using this applying this filter to first dates and romantic encounters. It’s during these times that I feel the need to quote the late, great Milton Friedman who said, “There ain’t no such thing as a free lunch.”

A filter, by definition, must filter. And what gets filtered out with Hell Yes or No is the beautiful, tangled web of uncertainty and surprise.

The major flaw in Hell yes or No is that it assumes we have a clear vision of what a “best-case scenario” might be. It may stack the odds toward favorable returns on time, but by using this filter as a default for romantic decision making, we run a larger risk than wasted energy. We risk the element of surprise. We avoid wading into the murky waters of risk where we can discover the unexpected.

Because, frustrating enough, inspiration follows action. And when I think about the big decisions that reset the course of my life, none of them were illuminated by a big Hell Yes or No sign. The bigger payoffs came from the biggest risks. And the glow of Hell Yes was only there in hindsight.

From Mark Manson’s Fuck Yes or No blog post:

“The Law of “Fuck Yes or No” states that when you want to get involved with someone new, in whatever capacity, they must inspire you to say, “Fuck Yes” in order for you to proceed with them.”

Now I’m no expert, but from what I can tell, Fuck Yes at First Sight isn’t correlated with Happily Ever After. When I met my wife, I felt more of a gravitational tilt than a binary decision. It was a feeling that burned out the entire spectrum of choice. And regardless of how she might tell it, I know I didn’t appear on her doorstep through a thick mist of Hell Yes. It took chasing, convincing, and a long dip into I don’t know…

Hell Yes or No has no place when it comes to true romance because true love doesn’t start with clarity. Falling in love is agony and ecstasy. It’s a ferris wheel that goes from outer space to the bottom of the ocean and everywhere in between. Falling in love is making a bet on an intangible feeling in hopes that one day two people will reach Hell Yes times infinity. And isn’t that what’s exciting about finding the right person?

It makes sense, however, that Hell Yes or No has caught fire and been added to our efficiency toolkits. Just take a look at the polarization of today’s hot topics and you’ll struggle to find what Aristotle called the Golden Middle.

Like Hell Yes or No, we love swinging the pendulum of opinion from one extreme to the other. We go from Reefer Madness to Weed is the cure for cancer, war, and toxic masculinity. It’s all or nothing. With us or against us. We even use the term “Switzerland” as a backhanded term for those who waver.

But now more than ever, as the narrative of Hell Yes or No tightens its grip around more aspects of our lives, I think we could all use more middle ground thinking. We could all benefit by coming to the table — be a romantic table set for two or a town hall meeting — with strong values and loose opinions, ready to be surprised.

“The limit of my language is the limit of my understanding.” -Ludwig Wittgenstein

Calibrating the way we make decisions is important. Swift thinking that aligns with our core values and initial instincts is a skill worth sharpening. But chiseling our options down to a binary Hell Yes or No is unimaginative and lazy.

Because as much we all want to define our desired outcomes at the onset, all too often the real rewards in life come in the form of something that was never clear to begin with. Hell Yes, Hell No, Must Be This, Can’t Be That — it all assumes that we can predict outcomes and keeps us out of the golden middle where golden surprises lay in wait.

Use Hell Yes or No to gauge initial feelings. But don’t ignore all the other shades of choice on the menu. Well, Maybe! Hey, we’ll see. I don’t think so, but fuck it, why not. It’s by using the entire spectrum of choice that lets us take the action required to one day sit back, smile, and say, “Hell Yes, I’m glad I made that decision.”

Please follow me on https://coreymccomb.substack.com

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Corey McComb

Author of ‘Productivity Is For Robots’ https://amzn.to/3 | Writing about freelance work, creativity, and human connection | https://bit.ly/corey-mccomb