What Actually Happens When You Ask the 36 Questions to Fall in Love With Anyone?

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Photo by Tyler Nix on Unsplash

Love is one of, if not the most powerful human emotion of all. No other emotion in our lives comes with the possibility of being overwhelmed with so much joy and the potential for causing so much pain.

When it comes to love I was a late bloomer. I was 25 when I met my first girlfriend. She and my second girlfriends became casualties of my selfishness and fear of being alone. Even though I stayed in those relationships for more than a year, I knew within weeks I would end them.

As a person with a tendency to fall hard and fast for women who came into my life, vulnerability was my kryptonite. A friend who I dated briefly when I moved to Los Angeles described dating me as dealing with an impenetrable emotional wall, in which my guard never came down.

When I was 36 experienced my first real heartbreak. And nothing will make you reconstruct your walls like the pain of a heartbreak. In that moment, I felt like nobody would be worth enduring this kind of hell for.

But, it didn’t just break my heart. It shattered the structures of my identity and everything around me. . It forced me to look at my beliefs and come to the realization that all my self worth came from external validation and was a house of cards.

From an Impenetrable Wall to 36 Questions

Now, looking back, after a few years of therapy, life coaches, energy healers, and other things that I affectionately refer to as new age bullshit, I realized the purpose of that experience wasn’t just to break my heart but to crack it open.

I’d never have had the courage to go through with one of the most vulnerable experiences you could have with another human: ask each other the 36 questions to fall in love with anyone.

Listeners of the Unmistakable Creative and close friends often joke that every guest on our podcast is a reflection of some problem I’m trying to solve in my life, to learn all the things we should have learned in school but never did.

How to fall in love has been enough of a theme that a listener once said to me “so who is this week’s relationship expert?”

Last November, I walked into the Boulder bookstore and the first used book I saw was Mandy Len Catron's memoir, How to Fall in Love With Anyone. A few days after I started reading it, I matched with a girl on Coffee Meets Bagel.

Given my line of work and love affair with books, it’s inevitable that books will come up in a conversation with me.

I sent her a picture of what I was reading. She remembered the article from the New York Times. After a few messages, at the risk of seeming crazy, I suggested that for our first date we ask each other the 36 questions

  • 3 Venues
  • 12 questions at each one
  • She picks the first, I pick the second, and we pick the third together

Because we were both in the process of moving from different states to Colorado, that first date didn’t happen until February. Six and half hours after we met, were eating pizza on Pearl Street at 1 am. She came to sign a lease for her apt and said she’d be back in a month.

Then, the pandemic started…. I never thought Donald Trump would cockblock me. “

Making a Podcast out the 36 Questions

Around the same time, my roommate started dating someone. And I had the idea for making an Unmistakable Creative episode out of the 36 questions. Fortunately, they agreed to be my volunteers and what unfolded was 29 minutes of the most breathtaking audio that my audio engineer and I have ever made. I hope you enjoy listening to it as much as we enjoyed making it.

Indian Matchmaking vs 36 Questions

It’s possible the only reason you have ever heard of me until last week is because of Indian Matchmaking. And it’s hard not to notice the drastic contrast between the 36 questions and the matchmaking process in the show.

In the South Asian Cultural Arms Race for Impressive Biodata, everything is about what’s on the surface. The questions to fall in love with anyone are about what’s underneath.

When we act out of fear of revealing who we really are, any connection we make with another person will be a house of cards. And when we can’t keep up the charade, that house of cards will crumble.

To fall in love requires depth, vulnerability, and the willingness to showcase your humanity and the unapologetic no bullshit version of yourself.

My most ridiculous filter for how much I can be myself around another person is to tell them I listen to MMBop when I snowboard. If they judge me for that, I know they’re not me for me.

As Simon Sinek says…..

My favorite definition of love is giving someone the power to destroy you and trust they won’t use it.

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