Q&A, values dissect, purpose

Values Dissect with Steve, Online Dating Consultant

You're in a function and you're relatively new to the scene. Other people may come up to you and ask "Who do you know here?"  Chances are the answer is going to be "Steve Dean" Eyes roll (in an endearing way) and everyone around you chimes an "of course..."

We acknowledge we are all more or less connected within 1-2 degrees of separation to this magical puppy-dog like unicorn. 

Who is he? 

Malcolm Gladwell would most likely label Steve as a "Connector." Steve makes it his business to meet someone new everyday. His intention is his passion- to provide tools, resources, insights, and create events so people can stay and become better connected online and off. How he chooses to do this had always fascinated me. If you know him, you'd know he's on 50 dating apps all at once. 

We met on OKCupid 4 years ago. I complimented him for his considerable attention into the detail and thought he put into his online profile.  It was that year, with his influence, along with his wide network of equally inquisitive and curious friends, that I was able to broaden my mind and grow increasingly comfortable in my own ever-evolving skin. In fact, all of the connections I've made through Steve in both NY and SF, had steered my life in a positive direction in terms of growth and personal development. Not to mention relationship, housing, and career opportunities.

Just recently, indirectly through Steve's influence and network effects, I was able to find a Burning Man ticket last minute...

So who is this guy? What does he do? The same curiosity that had led me to message him first on OKC asked him for the opportunity to dissect the values that drive his decisions and behavior. 

What are the motivating factors for someone to constantly stay plugged into other people's lives. Where does energy and passion come from? What do moments of connection look like for an Online Dating Consultant?

Check out this Q&A with Steve Dean, Online Dating Consultant to learn more.

August 11th @ Apartment in Brooklyn

T: What are your 5 Core Values?

  • Curiosity
  • Explore
  • Awe
  • Connect
  • Impact

T: Can you give me a brief summary of why you chose your values and in that order?
S: Most of what I do starts with curiosity. I’m a very dopamine driven creature. Curiosity triggers the exploration which leads me to a lot of awe. “Like oh shit, there’s a lot out there.” In the process of doing that, I like to find moments of connection whether with people, with systems, that momentary spark where you’ve gained enough perspective to understand something. The next step after that is how do you create impact? Once you see or are aware of systems in place, what can you do beyond that? And that’s when I think about: What’s the impact I would like to have.

I know I like to make an impact, but I don’t know where. Or how, necessarily. And so that’s how I have to default back into curiosity. Put myself back to beginner mindset of finding what’s out there, what needs the impact.

I think about that a lot lately. Especially given our current political climate, given what’s happening to a lot of countries fighting for their independence, given me stopping my work at a startup and deciding what my new version of impact is, what the most impactful and useful way is to spend my time.

T: WOW. There’s a lot there. So what is your mission?
S: I’m really reluctant to have a mission. Because every time I have a mission, it been thwarted by new knowledge.
I have a lot of evidence to support the notion that my missions are consistently wrong. So what is the cost of buying into a mission? This is partially my personality type. I’m the explorer type. I like to experiment on a lot of new things, be at the cutting edge, and then condense and distill that into takeaways that I can pass on to other people. So that they can then decide for themselves what is the most impactful way to spend their time so they don’t have to recreate the wheel.

For me to be tied to a single mission- one of exploration and discovery across multiple frontiers- it’s never just one. In the last couple of years, I’ve worked on multiple dating startups, an employment startup, a relationship startup, a mobile app startup. I’ve considered working in law, politics. I’ve done externships to check those areas out. It’s a consistent process of discovery and exploration for me.

One thing I never touched or ever considered within reason for me is a traditional career path. Where I was like “Oh, I want to be a lawyer so I need to get into a good law school.” None of that has ever appealed to me. The idea of being stuck in a single track that you can’t change or with minimal control over, for years on end, for me, that’s exactly the opposite of what I consider to be a healthy lifestyle for myself.

So to the extent that I can avoid having a mission, that is my mission.

That is my value that I offer the world. The core thing that I've stood for so many people, is a rejection of the status quo. It is questioning, “why is it that we make gendered assumptions about the world. When we fail in our relationships, it’s usually because we are projecting a set of norms onto our partners rather than connecting with them. Rather than letting them speak their truth, we are inserting our own truth over them and being domineering.

There are so many different things that I learned in my own relationships alone that made me feel very strongly about this. My core strength is not doing the things that everybody else is doing. Finding out what I can learn from all these other little worlds I’ve been exploring, how to communicate, relate to people, what kind of relationship setups make the most sense, then collecting a thousand of perspectives to see how right or wrong my assumptions are.

T: So how does your mission or rather lack of mission tie into your values? 
S: I think they are all intertwined. Or maybe they are intertwined because of who I am. For me, I have never been satisfied with what currently is, or what I am told. I went to a Catholic school growing up and I was always really upset with the types and quantities of information I was given. I was told in 1st grade that I wasn’t allowed to read any books that were higher grade level than 1st grade reading. I was really frustrated by that because I read every book on the 1st grade reading shelf by month 1 of school and had asked "What’s next.” And they’re like, “well you can’t read anymore.” And I was like “This cannot possibly be the education system that I am embedded in.”

And granted, I don’t think my thinking was very broad at the time. I was just frustrated that I wanted to read the 2nd or 3rd grade level books but they wouldn’t let me. 

So I’ve always been frustrated with status quo or arbitrary restrictions that are placed upon ourselves.

I was always curious and would ask “what else is out there?” I was told “this is what it is” in my religion classes. I was always thinking, “Well, what else could it be? Why is it that?” What grounds is it for this normative claim, about who wrote what book, and whether this the only possible interpretation of the scripture we are looking at. So that’s where that started. This curiosity…and the next part for me has always been exploration.

Exploration my next value. It’s not just enough to be curious that usually motivates you to find out what’s out there. I remember right after college, I got into a relationship where we realized that everything we’ve been told about relationships wasn’t sufficient to capture what we wanted to have.

We wanted something that was not monogamous and every variable we had we were weighing and measuring in that relationship, all the people we wanted to see or were currently seeing, all the different motivations and how they would project over time –- none of that made sense in a monogamous relationship. So we thought "okay, what else could we explore? There has to be something else out there.”

We started researching, we started creating little excel sheets together, and we decided we could create a new relationship. And not just a new one, because there are a lot of different types of relationships out there that are woefully underexplored and not fleshed out particularly well. But we wanted to build one that was perfect for us. And so every step of the way (we are now in that 5 and a half year relationship), we are still exploring every day to see what new ways we can relate to one another, increase our trust for one another, increase our capacity to care, to become better people.

Exploration has always been part of that. My entire work, all of my work is tied to exploration. Because what I'm trying to understand better is how people can communicate, how people can get over breakups. You know in dating consulting it is all "What are the problems people can experience in dating.” I can't just turn this into an easy solution.

For me, I usually give advice based on whatever I explored on my own. What I find to be particularly effective, which perspectives have I gone out and collected to understand whether this is a qualitatively a good piece of advice.

If I try to give someone a piece of advice and they say “oh no my perspective invalidates this, this would be right for these kinds of people, but I’m not that type of person,” then my relationship advice does not make sense for their particular situation. That happens for me sometimes, and in those cases I need to reconfigure and ask “Okay what part of my advice is wrong, doesn’t scale or adapt to certain situations? How can I change that advice, because I can’t assume I’m always right.” I have to assume I was right until proven wrong and now scientifically i can go back and forth with a new hypothesis, a new way of relating. So I guess that is a decent review of my quest of that. What was my 3rd one?

T: It was Awe.
I think the fun part that keeps me from wanting to explore is that wonder and awe. It’s that recognition the further I go, the more I discover. Einstein says all of human understanding is an ever expanding circle with infinite blackness on the outside. We have this little light which grows when we learn more and we only end up illuminating how much more blackness is actually out there.

Every time we think we know something, it just keeps getting deeper and deeper. We have new discoveries, new breakthroughs, new ways of conceptualizing the world. So I find I’m always surprised…by something…or at least I feel I want to be surprised… I should put it that way.

I’ve gotten better at discovering how people think, how they relate. What the common problems are and how to overcome them. So I’ve been surprised less..which is frustrating to me. Because it means I’m getting better or I have more predictive models of how the world works. Which is a great thing for me, professionally. It means I’m doing my job right. But one of the things I really want and which makes makes me satisfied in doing my work is that for the longest time (and hopefully increasingly so in the future), I’ve encountered those moments that make me say, “holy shit, I didn’t even realize that this is a way of framing the world and that this is even more predictive or explains even more of the variation that i see.“ 

So when I talk about my “Friendship-First Approach to Dating” it's one where like instead of just trying to find someone who is immediately compatible from the get-go, we accept that, probabilistically, we won't find those people every time or all of the time and instead we should just appreciate the fuck out of those people who do choose to spend time with us. We design really fun dates so we can appreciate them doing whatever makes them awesome people, independent of whether they are compatible with us. And by taking that approach, we can create long-lasting friendships and create referral networks where even if we are not compatible, we still get a boost from this person referring us down the road to 10-20-30 new friends, new partners, new humans in our lives.

That for me is a highly predictive model of success in dating. Feeling very strongly connected with people and building close networks of people you care about. And so I look at that as something – from when I first explored how far I can go, how powerful it can be - I was filled with wonder. "Wow this is really cool, this is better and better everytime I try it. Is this really the solution? Is there a better frame?” I haven’t found one yet. But I am open to it and I keep on looking at other little areas.

The next thing I’ve been exploring is how to build intuition. So you don’t have to think through steps on how to interact with someone. You can intuit from any number of variables. It could be their body language. Someone’s facial expressions. Vagal tone. Words that they choose. Lexicon. These are all worthwhile data points to explore when we build up an intuition, but there’s always more. There’s the question of pheromones. Is that something that is actively influencing us? Could there be ties to time of year, planetary alignments. Get a little horoscopey. I like to seek other explanatory variables that have some degree of evidence to back them up.

Basically every time I discover something new, I am filled with that sense of awe. I thought I was getting better and better at predicting how the world works and this thing just throws a wrench in that. And I’m like “Oh shit, Wow. That’s really cool.” It just feels momentarily, the world is once again magical. And science then encroaches; science tries to explain and remove the magic, and then every time it gets to a certain point, we get surprised all over again.

T: There’s definitely some aspect of innocence and childlike wonder and awe in how you view the world- which is infinitely more majestic than it is to just be very black and white. I appreciate that very much. So let’s talk about Connect! 
S: Connect- So when it comes to connection and why I like it so much.. for me, it’s really easy when you’re getting too cognitive about the world and too interested in picking it apart and finding explanatory variables, using jargon that sounds gross to so many people. You can lose the capacity to connect with people. You can create a lot of moments where you people feel you aren’t really hearing them. You can easily lose people when you become too scientificky or rational.

So I like to balance all the work I do in the cognitive side, the rational, the scientific side with a strong desire to experience those moments of connection with people who are on the emotional side.

And I think the two are intertwined but I frequently find empathy and emotion are the basis for feeling strong connection. It’s been really powerful for me to think through who are the people I actually connected with. What moments that stand out to me in memory that I felt so close to someone that I could tell them everything, that there was nothing about me I couldn’t convey to them. 

For me, friendship -- genuine friendship -- is a flow state. When you are working, you have a lot of time when you’re not really in it, and other things can still distract you. But when you enter a flow state in work, it’s like everything becomes simple and easy and obvious. There are no setbacks, you just have the feeling of total fluidity. If there is a setback, you get over it immediately because you’re in your avatar state -- a state of flexible forward pushing clarity.

And for me, that’s what friendship is. That’s what the connection is that we seek with people: the ability to remove all of the walls, the ability to be in a flow state with another person. For a lot of people this happens sexually...and for a lot of people this absolutely NEVER happens sexually.

It’s kinda interesting to see that sex is something that can be very easy to flow for some people because that’s a very natural state and for others there’s so many inhibitions tied into it, it’s nearly impossible to get into flow, because as soon as things get too sexual, they get too nervous.

Friendship I think is a good example, when you are in a good friendship it feels like perpetual flow. That person just shows up at the door and you’re already relieved to see them, happy to see them. You can talk about anything. You can expose the core of your being and they are right there with you.

Those are the feelings of connection I shoot for. I try to see in my work, is this something we can optimize? People are going to hate me for that because I’m trying to take something beautiful and natural and systemize and optimize it. I hate that, too. But I try to do it in a way that doesn’t become artificial. I try to do it in a way I can own up to.

If I couldn’t own up to someone in realtime and tell them what it is I’m doing, then that to me is not connection. I’m not doing a good job in connecting with someone if they sense there is an agenda. So I always have to check in with myself first and say, "What is it that I really want from this person, what is it that I think this person has to offer?”

To experience true connectedness with someone, I can’t simply exist in my own mind, I can’t be cognitivizing everything. I can’t just let them play into the machinations of my research, it’s more like I have to forfeit my own ego; I have to create a space where we can share together, where we can be vulnerable together, where we can talk about anything. Trying to get that to happen on a first date has been endlessly fascinating for me. 

It’s not easy to be vulnerable with someone you first met. What are the questions you can ask someone. What are the moments you can share together? What are the places you can go? What are the profile details you can add ahead of time?

In online dating, there are a lot of different variables that can allow you to feel more or less connected to someone when you first meet them. And over the course of those first couple of hours, there are pivotal moments where you experience a level of vulnerability and where you create that space together. And so for me that’s very much what connection comes down to. It’s creating a sacred space together that you and another person can share. And I absolutely love doing that. It complements the very scientific and analytical part of me that is always trying to synthesize new facts and information about the world and new frames. This moment of connection allows me to put that to the side and simply relish in the experience of sharing a moment with someone.

T: Connection to you is entering a flow state where you feel very comfortable exposing yourself. What you do in your work is breaking apart and understanding what are those questions that can expose you in a very vulnerable way while relishing in this shared sacred space with someone. There’s a lot we can all learn from that. So the last one is IMPACT!

S: This is where it ties together. Everything that I've covered already. My curiosity leads me to go out and explore. When I explore, I'm surprised. Things are awesome. As I'm synthesizing all these details about the world, I’m getting a bit heady so I use moments of connection to feel very grounded about who I am and what I stand for. Ultimately, this leads me to thinking, "Okay I have this information now; I have capacity to connect to people; I have these moments of intense connection. How do we scale these up? What is the actual net impact of all of this? Why am I doing any of this? What is my net impact on the world?

Yes, I can experience this, and this is amazing. Moments of connection is something I wish for every person in the world. How can we make that happen? How can we make sure everyone feels moments of connection that make them feel grounded in their shared humanity? This would help mitigate political differences, social differences. It’s these moments where we take someone else's perspectives and giving them space to share their story.

So when I think about impact, how do I take everything I'm working on and everything I discovered and channel that into something bigger than me? Not just random cis white dude writing a blog post on Medium and what he’s learned and HIS experiences. It’s gross and I hate that. I hate that’s how currently that’s my strongest outlet, preaching to random people. That for me makes me feel inadequate that I’m not doing enough. Kind of like the street preacher syndrome. 

I don’t want to be that person. I don’t want to be in this echo chamber shouting out to nothingness. 

What is the positive impact I can have? This leads me right down the curiosity path. There’s a lot of people who have a lot of different forms of impact. Sometimes it’s through inspirational videos that go viral. Sometimes it’s through organizations -- create an organization that can outlive you. Sometimes it’s through political organization -- create a state. This is all within the realm of possibility right now. It’s very fascinating that everyone can have some level of impact on what’s happening in the world.

And the question is: “What do you want to dedicate your time and attention to?” For me, this is where I get tripped up a lot. Because I'm always aware, like I said in the very beginning, every time I try to dedicate a lot of my time and attention to one thing I think that this is my path for maximum impact, I typically learn sooner or later that there are better paths for maximum impact, or there is a different kind of impact I want to be having.

If I decide right now my best impact is dating advice, is that really the the best thing I can do where my 5-year-from-now self will look back and say, “Steve, why did you just spent 5 years giving advice to people on Tinder? Which people were actually positively impacted by this? Is the world really a better place because of this?"

This is how I keep myself in check. What is the net effect of what I’m doing, and can it be larger? These are the existential anxieties and qualms of a dating consultant in the modern age.

"Every day it seems like my life is recreated anew. I've been a digital nomad for the last 5 years, so sometimes I'm literally waking up in a new bed every single day for weeks on end. There's no end to the discovery, no end to the learning, no end to experiencing the life in all its messiness and confusion and excitement and serendipity. But I live for this. There's a world to explore, and there are worlds within worlds that go unseen until we discover them." 

"Every day it seems like my life is recreated anew. I've been a digital nomad for the last 5 years, so sometimes I'm literally waking up in a new bed every single day for weeks on end. There's no end to the discovery, no end to the learning, no end to experiencing the life in all its messiness and confusion and excitement and serendipity. But I live for this. There's a world to explore, and there are worlds within worlds that go unseen until we discover them." 

Well there it is, the inner workings from the mind of a dating consultant. The light and the dark behind the man who lives by unconvention- who consistently and constantly forms new relationships online and off. How does he do it? 

Listening to him speak with such nonstop flow and poise, I can vouch that he is 100% real with his conquest to tackle the intricate mysteries of the world through his own personal exploration. It starts with curiosity. Intention follows through as wonder and awe derived from connection fuel an individual’s journey towards impacting the world.

Regardless of whether any of this has any resonance towards your own personal lifestyle, hopefully the message of constant exploration over the undiscovered appeals to our very basic human nature and our right to question  “why” and “why not.” 

Another interesting insight made is the realization that within all of us lies multiple accesses to impact. How can the strength of your character and curiosity help guide your path? We can’t claim we have the right formula for “success.” All we can say with certainty is that life is a mystery. Mind as well explore and see what it’s made of.

Thanks Steve for paving the way and allowing me to explore the deep consciousness of your mind. It's been real. 

Steve Dean is an NYC-based online dating consultant and digital matchmaker. He currently creates resources for jobs, housing, dating, and personal development on Patreon


The Values Dissect is a practice where we pick apart and discuss 5 values that have gotten you to where you are today. How these interrelate to each other helps us better understand the driving forces of why we do the things we do and to what purpose.

I invite you to share your personal truth and bring to light past, present, and future in this telling tale of who you are and who you aspire to be. Sharing how your values align with your mission and expressing your intention in such an open and raw way has the ability to inspire others to do the same. 

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