What I Learned From the Worst Date of My Life

“This must be how natural it is for normal people”, I thought cheerily, as Amy and I continued grooving to the rock-reggae sounds of the band we were seeing in Denver. We’d had a few drinks, and I was being bolder than my usual self, dancing close with her throughout the night and very much enjoying the touch and contact.

I had reached out to her on MySpace, and a week ago to the night we’d had an amazing date visiting an art museum, getting some drinks, and making out before we parted ways for the evening.  It was clear she liked me, and I’d been doing a lot of work on myself and was feeling more attractive than I ever had before.

As the night progressed, I kept dancing with her more and more, not really noticing the moments she’d break away to get some space for herself.

The band played their last song and we grabbed our coats to head out back to the car, which was a few city blocks away. We chatted about the show as we walked, she’d thankfully enjoyed the band as much as I’d hoped she would.  Feeling good, I put my hand around her waist and pulled her closer towards my side as we walked.

And that’s when it happened.

Amy stopped suddenly, turned, and literally shoved me away from her with both hands.

GET OFF OF ME” she cried out.

I immediately jumped back, contracting and deflating, not even saying a word.

She noticed my shift, and somewhat tried to reassure me, “It’s not that I don’t want that, trust me, it’s just too much.  I’m not used to it”.

I then went completely numb and totally withdrew into myself.  I was no longer the attractive man who had been doing a lot of transformation. I could barely talk the rest of the night, and we had a long car ride home.  She asked me once or twice if I was okay, and I couldn’t even really face her to answer. I collapsed more and more into myself, feeling shame that I had made her so uncomfortable, and that I wasn’t showing up like a man.

I could barely sleep that night, replaying the night over and over in my mind, auditioning the many scripts what I might call and say to her to fix things.  The next morning I felt terrible, totally introverted, shut down, and extremely numb. I spent the whole day eating and playing Halo. The pain and sadness was just too much for me to bear, so I stayed locked up in my numb prison cell.

And, of course, we didn’t wind up together.

My story isn’t an uncommon one these days – today’s dating scene can be hard, especially for those of us who more often than not have felt awkward with women throughout our lives.  We’re really solid guys, who really do care for and respect women, but we get tripped up by our anxiety and fear of rejection, or so overwhelmed when we’re actually rejected that we fail to meaningfully connect with the women around us.

This story of my collapse with Amy is just one example from my life.  From the moment I hit puberty on I was straight up afraid of women, totally unsure about how to approach, flirt, and date women I was attracted to. It was such a challenge for me that I never even kissed a girl until I was in college, didn’t lose my virginity until I was 26, and didn’t have a bona-fide relationship until I was 29.  I carried a sense of deep pain, sadness, and shame that I had missed out on so many opportunities to be “normal” like everyone else and innocently date partners as I grew into adulthood.

So much of our self worth as men is tied up in our ability to connect with women, and it’s so common for us to have long lists of moments we regret not showing up more fully.  “If only I had made a move” or “I should have told her X”, or “Had I not totally overreacted it would have been fine!” We all have lists that could go on and on, and almost inevitably, each moment of regret gets fused with shame and together they become a story about something being fundamentally wrong with us.

This internalized shame can be crippling for us as men and will often impact us far beyond just dating and relationships.  Throughout my life I’ve collapsed many times, and like many men began to build up coping strategies to numb myself out from the pain.

The day after that infamous date I withdrew into video games, unable to feel the weight of my disappointment and shame about what happened. Another time it was sitting in my bedroom for 3 days straight, eating nothing but $5 Little Caesars Pizzas and binging the entire first 8 seasons of the American Office – when I only had $300 in my bank account and no idea how I was going pay for rent in a few short days. Then of course there were the hundreds of hours I spent numbing out with internet porn and masturbation.

I knew things like this were making the situation worse, which made me feel worthless and drove me further down into shame and shutdown.

But the thing is, these things didn’t happen because I was worthless. It happened because a certain part of me had been blown out.

It happened because of the compromised state of my nervous system.

Our nervous system is the information network of our body – handling all communication between our physical and emotional sensory input. Like any network, it can be overloaded and stop working, similar to a traffic jam on a freeway, clogged pipe, or blown out power circuit.  When we’re young and our nervous systems are still developing, these moments where we get overloaded actually leave energetic kinks in our pathways. As we grow older, they can be overly sensitive to situations that are similar to what caused them, wreaking havoc on our behavior and how we’re showing up.

For me, the moment Amy pushed me away triggered some deep energetic kinks in my system that related to having insufficient touch when I was a kid growing up.  That part of my system exploded like a landmine, overwhelming my nervous system and causing me to have a reaction that wasn’t really commensurate with what was happening (she even said she liked me!!). These kinks are also usually trapped in time, so in my case I completely regressed back into the nervous system of little boy I once was, frozen from a lack of touch.

As intense feelings that threaten to overwhelm our nervous systems build up – we increasingly turn heavily towards activities to try and self-soothe and regulate ourselves.  These activities are often attempts to discharge, replace, or numb out the sensations that are threatening us. At their most dangerous, these activities can become full blown addictions, habitual wirings that we rely on to survive, be they drugs, alcohol, porn, sex, social media, television, or fantasy.

We change everything about how we show up in the world when we bring awareness to how our nervous systems work. Instead of taking these moments of overwhelm or collapse and internalizing them as stories about how something is fundamentally wrong with us, we can realize they’re simply times where our nervous systems hit full capacity.  Be it when failing to approach a beautiful woman, freezing during a critical meeting, or overreacting when a situation wasn’t going our way, having this framework can let us release so much of the shame we carry as men.

It also offers us a very clear pathway for how to move forward in our lives as men. To show up differently in the world, we must simply expand the capacities of our nervous systems.  The stronger our nervous system, the more we’ll be able to boldly interact with women, take chances in our careers, react promptly in times of crisis, and show up more playfully in any given moment.  This resiliency is something we can cultivate in a variety of ways with intentional practice that manifest in two particularly powerful strategies.

The first is the therapeutic route, and works by clearing out those old energetic kinks. We’re essentially energetically rehabbing the existing parts of our nervous system that aren’t flowing. This can include talk therapy, somatic therapy, bodywork, plant medicines, and shadow work.

The second is to get better and better at running more energy through our systems, be it uncomfortable sensations or joyous pleasure.  This is the yogic route and is more about building capacity – sort of like building new muscle tissue – and can include yoga postures, breath work, cold therapy, and strength training.

Each route is absolutely essential, which is why I incorporate them both in the work I do with men. Practicing them transforms us – allowing us to cultivate one of the most essential masculine attributes: presence.

Presence as I define it is the state of having a nervous system that is both relaxed and alert – with a free flow of information between all three of our energy centers: our head, our heart, and our guts.  A man with presence becomes a beacon of safety and trust in the world, un-phased by whatever situations manifest before him. Our nervous systems become true gifts to those around us, as we bring a feeling of peace and freedom wherever we go.

Presence is one of the things that woman long for the most in men, and exactly the thing I lost on my date with Amy.  I’ve learned to cultivate it more and more throughout my life and it’s impacted every aspect of my being – my relationships, my sexuality, my career, and even my health.

If you’d like to learn more about presence and a few other key attributes that can work together to deepen your relationships with women and help you lead a more unapologetic life, please checkout my free webinar below.



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  1. You’re upset because she didn’t want your hands all over her?! Seems you seek a physical connection vs. a mental one. Why do so many men feel entitled to touch us for self-empowerment, or feel that it’s okay when it IS NOT? No one feels sorry for you.

    1. Hi Joy, that’s not really what the article was about. I had unconscious shadow wounding from my childhood around touch that was driving me – she set a very healthy boundary and it triggered all of that for me, which then kicked off a painful journey of collapse and then healing for me. This article has nothing to do with me wanting anyone to feel sorry for me, it has to do with men like me becoming aware of our physical, emotional, and spiritual wounding and taking responsibility for it because of what happens when we don’t.

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