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Dating: What if failure wasn't an option?

Society puts so much pressure on finding “the one” that it’s easy to feel like a failure anytime a relationship ends. But, I mean, do you really buy into the narrative that there is only one person in this entire world who is made to complete you? Smells like scarcity to me. Yet, this is the dominant paradigm in mainstream U.S. culture. It’s a paradigm rooted in hetero-normative, mono-normative, capitalist patriarchy. And what do these systems have in common? They share a philosophy of “dominance over” (a trauma response rooted in scarcity).

Societal pressure to find “the one” permeated into my work life where I worried my failure to climb the relationship escalator would negatively impact my income. I was 23 and working at a startup in St. Louis. Even though my boss was just 5 years older than me, he was already married with a newborn baby and a house in the suburbs. And since society only considers your relationship to be “serious” if you ride the relationship escalator, I feared that my failure to ride the escalator would mean my boss would take me less seriously, which would hurt my chances for a pay raise. On top of that, I was a closeted trans man presenting as a queer woman. And he was a cis het white man well on his way up the relationship escalator. I kept stumbling over the first few steps.

Like most human beings, I internalized the beliefs of the world around me. I grew up in St. Louis, Missouri where the hetero-patriarchy was alive and well. I internalized the belief that my failure to ride the relationship escalator meant that I was a failure. Each time a relationship ended, I would feel exposed. Like a light was being shined on the pieces of me that felt unlovable and undesired - as if pointing to a flaw in my character for everyone to see. And at the tiny startup where I worked, there felt like no place to hide.

Tying my sense of self worth to the longevity of my relationships took the joy out of dating for many years of my life. My fear of “failing” at love was driving me to settle for less than what I deserved. I felt pressure to follow the script of the relationship escalator: move in with my partner, meet the parents, get a dog, get married, have babies, retire together, etc. This external pressure made it difficult to notice even the most obvious incompatibilities. I was trying so hard to prove to the world that I was serious (to advance my career) that I was suppressing my needs and desires for the sake of longevity.

From Scarcity to Abundance

The truth is - dating is all about experimentation. It’s an opportunity to collect data about what you like and which areas of compatibility are most important to you. Because, sure, you can have really great sex with someone - but what about all the other facets of compatibility? For example:

  • Do you have similar expectations around Covid safety? 😷

  • Do your spiritual values align? ✨

  • Do you want kids? 👶🏻

  • What is your vision for your life? 👁

  • How do you see your future? 🔮

  • Are you working a 9-5 office job? 👩🏽‍💻

  • Are you living in a tiny house and traveling the world? 🌍

  • Are you engaged in the community? 👩‍👩‍👧‍👦🌱

  • Are you invested in social justice? 💗

Which factors are deal breakers? Which factors are the most deeply tied to your long-term happiness?

Success is not about longevity - it's about living in alignment with your truth. Success is being able to acknowledge when there's not enough compatibility between you two for things to continue (as much as you wish they could). But even after a relationship ends, nothing can take away the wealth that you have gained through that experience. Each relationship is a data point that gives you important feedback about your preferences that you can apply moving forward. The more you learn about yourself through dating other people, the more confident you will be to say "yes" to someone who meets you where you're at. And, I mean, what better way to learn than trial and error? Did you really expect your first or second relationship to be “the one”? That’s a lot of pressure! 😱

The sooner you’re honest about your incompatibilities, the smoother your life will flow in the long run 🌊🌊🌊. You won't grow old and slowly regret over the years all the little things you're missing out on because you had settled with what felt safe. Being able to say “No, thank you. 50% compatibility isn’t enough for me. I need at least 85%” comes from a place of abundance. Being afraid to say “no” because you might not find something better comes from scarcity. That’s when fear is running the show. (And, by the way - there’s no shame in being afraid. We’re all living within these oppressive systems that perpetuate scarcity. It’s natural!) Saying “no” to something good to create space for something great is an act of courage! It's something to celebrate 🌺.

Dating is not a game of musical chairs - it doesn’t have to be a frantic race. Next time you feel pressure to settle with "good enough", simply pause to notice and ask yourself:

  • Am I satisfied with the daily experience of my life?

  • Which ways am I living in alignment with my intentions and values?

  • Which ways am I living out of alignment with my intentions and values?

  • What small changes can I make to get back on track?

Old Paradigm: If I can't prolong a (romantic) relationship, I must be flawed / a failure. New Paradigm: Relationship endings reflect incompatibility, not failure. Success is living in alignment with my truth enough to admit it wasn't going to work out.


You don't have to walk this path alone. There's a community of folks developing secure attachment over on Patreon. Patreon members get exclusive access to Relationship Hour, a monthly support call where you can connect with others along the path, ask questions and celebrate your progress. We meet every first Thursday of the month at 4pm PT. You're invited!

Patreon members also get exclusive access to guided meditations that help build self trust + confidence. New meditations released monthly.

In addition, you get 10% any workshops or classes throughout the year, including the energy healings that happen every third Saturday of the month from 11am - 1pm PT.

While each energy healing is in service of building secure attachment, the theme varies each month. November's theme is Leaning into the Unknown. Let me know what theme you wanna see next!

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