Sam Overton: Improve Your Dating Life, Travel & Become Self-Sufficient

Sam Overton is a dating coach, entrepreneur and founder of Fluid Social.

For those unfamiliar with you, can you give us a quick rundown of your background and why you decided to become a dating coach?

So I graduated from Nottingham University in 2015. For the final two years of university, I started working with students who had high-functioning autism. I would help them build social circles and develop a social life. I would sit in meals, dinners, lectures, seminars with these students and I would help them develop their social skills by monitoring their behaviour, and then creating a syllabus which I went through with them to systematically improve. I did this for about two years.

In the final year of working with them, the company that I was employed by asked me to begin helping these students with dating and meeting women. I did that work specifically for about a year, and then I noticed that this was something that wasn’t really provided as a service, so I began this sort of niche, helping guys who had social difficulties to meet women.

I wanted to help guys that didn’t necessarily have compromised learning faculties (like autism spectrum disorders). I wanted to help guys who genuinely just struggled socially. I saw a bigger market and began working with neurotypical men, helping them to meet women. I’ve been working with neurotypical guys for the last six years.

Your advice centres around meeting people in person. Why do you think this is the better approach in a world where more and more people are trending towards online dating?

I think precisely for that reason it’s important. We have evolved as a species for our ability to communicate en masse; for our ability to transmit and pass on information. This ability is the very reason we’ve survived. Talking to someone face to face is an incomparable way of communicating rather than talking over text messaging. It’s much more direct; it’s much more intense; your mind remains much more active; there are so many intricacies with eye contact and noticing how someone’s feeling. 

I think approaching women, in many ways, is the best sort of microcosm for overcoming difficult challenges that I can think of. You’re going out, you’re doing something for yourself, you’re chasing, you’re making an opportunity happen that doesn’t just come to you, you’re having this sort of physical, intimate connection and you’re also having this emotional connection. That’s where we grow – we grow in that space of intensity and real physical connection.

Dating apps, technology, zoom calls, all of this is, in some way, detracting from the vital experience of being human – interacting with nature; interacting with other human beings face-to-face, where you can feel the heat from their body, you can see the red in their face. To me, these are incredibly humanising experiences, especially for a young single man.

What’s your own philosophy around dating, considering how polarised advice can be online?

Yeah, that’s a really good question. I see two polarities not as right or wrong, but just as the natural result of each other. I tend to see it as though, whichever point is directly between them, is the balance that they are sustaining; where everyone ideally ought to be.

My own philosophy is, everyone has a sense of what’s right and wrong. You know that it’s okay to go and talk to someone; you know, deep down, that there’s nothing wrong with giving someone a compliment from a place of good intention, telling them they look cool, or you like their style, or they look nice. Virtually everyone who’s sane of mind knows where the line is, what you should and what you shouldn’t say; what you can and what you can’t say to be respectful when doing so.

Whenever I get messages from clients saying, “Sam, I don’t feel like it’s okay for me to go and say hi to a woman, what if she doesn’t like it? What if she gets offended? What if she thinks I’m harassing her?” I’m just like, man, you know that that’s not what you’re doing. This is only because you’ve been reading articles by one of these radical sites. Just stay away from it. It’s like eating junk food. It’s just a bad habit to be paying attention to the extremes. Do what you know to be respectful and kind, and have the courage to do that.

How would you contrast your outlook on life and general sense of self, now, compared to before having poured into your social and dating life? Have your values changed?

It’s easy to forget how far you’ve come because you’re comparing yourself to how you were yesterday, rather than how you were five years ago. The feelings, the emotions, the inadequacies that you felt five years ago, are just a vague memory to you now. So it’s very difficult when I’m asked a question like, you know, how have your values changed from when you started?

But I remember, before I learned that I could improve my dating life, social life and my overall confidence as a man; before I learned that I could systematically improve through actions that I could take, I thought that I was unattractive to women. I thought that I just didn’t have the genetic ingredients of a man that would be able to have a beautiful girlfriend, or date beautiful women, or have a cool social circle. I just thought the ingredients were wrong and it was that simple.

I think the most important thing that I’ve gained from engaging in this process is a relationship with myself – meaning, being able to look at my situation and ask what needs to be done to improve it or to change it.

A lot of young guys feel stuck. What would your advice be for them - especially those who feel that the odds are stacked against them (i.e. by their looks, height, etc.)?

You have two options. You can either say, well, life wasn’t fair to me; I was born with certain disadvantages, and therefore, I’m going to fall into nihilism. Or you can say, right, well, I’ve got certain disadvantages in this area, I’ve probably got advantages in other areas, and that is the way it is. Let me optimise my life in whatever way I can with the ingredients that I have.

Stop comparing yourself to other people and just look at what you can do with the tools that you have. You can choose either of those paths, but one of them is going to be rewarding and one of them is going to be deeply miserable. But you get to choose.

I’m not understating the pain that you might feel from being unpopular or feeling like you’re not worthy of love, or admiration or attraction from women, I just think it’s important to know that you can definitely defy that. There are plenty of people that have proven that you’re not restricted by your race, by your country of origin, or by your height. In every case, I can find someone that’s doing well. There are plenty of role models, so find them.

A lot of guys are held back by a fear of rejection. How has your relationship with fear changed over time?

That’s a really good question – it’s probably changed more than anything else. ‘Cold approach’ is a very extreme way of addressing one’s fear. And it constantly is. It never really subsides – it gets easier, and you become much less intimidated by the act – but there’s always a level of psychological preparation when you’re about to meet someone new and express attraction towards them. It’s difficult every time but I think it’s a great doorway into a greater appetite for risk.

It’s very much like a muscle. Because just like a muscle, it grows with more flexing and it diminishes or atrophies when you don’t flex it. But once you flex it enough, you gain muscle memory. It’s exactly the same with social skills. You get rusty if you stop. If you have a pandemic like the Coronavirus and you get locked inside and you don’t really have the opportunities to meet people in the same way that you had before, you feel almost like you’re going back to square one, but when you get back out there again, everything floods back to you. The lessons are permanent.

As you find that in social situations you’re becoming more confident and you’re expressing yourself more, then a lot of the fears that you may have – say, travelling to another country – also subside. You become more confident around people in general.

When you’ve proven beyond doubt that you are able to connect with people; that you’re able to meet a woman in the day and go on a date with her that evening or stay with her for that day – maybe she’s visiting from another country and she ends up staying with you for a week and then going on – when you’ve had all of these experiences, you look at something like travel as a great adventure, rather than something to be afraid of.

Where’s the line between striving for improvement and accepting yourself?

Those are two sides of the same coin. Accepting yourself is just having an honest understanding of the way things are right now – it’s not saying that everything right now is as good as it could be, it’s just saying everything right now is as it is. Only can you strive for improvement when you accept that everything is the way it is.

You must accept yourself the way you are to know what to do next; to know how to improve. If you have hubris, or arrogance, and believe that everything is as good as it could be (which is the opposite of accepting yourself – it’s having a disillusion about the way that you are), then you’re unable to strive for improvement because there seems no room in which to improve.

And conversely, if you believe that you are worse than you really are; if you believe you are horribly ugly, too short, stupid, unlovable, it’s very difficult to improve from there as well, because you are not all of those things. It’s just about understanding and accepting the objective reality.

How do you deal with impatience?

When you have a few days that feel like you’re racing in the right direction, it’s wise to understand that you’re probably going to feel the other side of that coin. It’s a really common thing to trick ourselves into thinking that there’s a quick fix to everything. But I think there’s a function to that sense as well. Often that does provide you with some motivation – some momentum – but then you realise that it was an illusion, and the quick fix is never really sustained.

I think many people go through these phases. It’s important to understand that the best phase that you can be in is not this supercharged, hyper confident phase, because it’s simply not sustainable. There’s an old analogy comparing an onion plant to an olive tree – the onion plant is old in 9 weeks, but the olive tree lasts hundreds of years. Instead of racing to grow and then losing your motivation quickly, strive to grow incrementally, building strong foundations in the direction of your goals.

Your life is optimal when you proceed through your days with a sense of peace, easy confidence and calmness, knowing that you’re doing something towards a goal every day; something in the right direction every day. If you can just settle into the flow and the rhythm of gradual improvement, then that’s sustainable.

It’s all down to positive habits, and trying to instil more and more positive habits and rituals into your day. And the easiest ritual when it comes to social skills is to get out of the house. Whatever opportunity you have to be in the company of other human beings, do it. We have to think small when we’re taking these steps. People can be put off by the incline of that slope and the seemingly massive step. But if you just take the first little step, it will encourage you to take the next one, and the next.

What’s the greatest mantra that you’ve lived by?

There’s been a few but one of the most important, in terms of actually being actionable, is “Go before you’re ready.” We are always waiting until we feel ready to do something, to go and do it. We might think “I’m not ready to become a coach, or I’m not ready to start my business, or I’m not ready to go out and meet women.” But the truth is, the only way to be ready is to go and do it.

Only by doing it will you make yourself ‘ready’ in the future. There’s never going to be a point where you’re suddenly feeling ready, because it takes overcoming that obstacle that you’re scared to do right now, in order to reach that elusive point.

That’s been really valuable for me because it’s not just a mantra that sounds nice, it’s something that you’re reminded of daily when saying, “I won’t do that now. I’ll do that a bit later. I’m not ready for that right now. I’m too tired to do that right now.” It’s like, no, but if you go and do it, you’ll wake up – the act of doing that will wake you up.

How has travel shaped you? Where’s your favourite place?

The perspective we have on the world is linked to what we physically see in our environment. Location and mindset are interlinked. You may think that your life is a certain way because you’re getting out of the same bed every morning, walking down the same street, going to the same job, meeting the same people – that is literally locking your brain into a very limited pattern; a very limited paradigm.

What travel does is free your mind from all of these trappings. Your mind is open because it’s no longer constricted by a familiar location. You move to a new country; you see new things; you’re able to think in a way that you weren’t able to think before.

There’s no family or friends to look after you; you’re on your own and that’s not a bad thing. You have to deal with the feelings of fear, you have to deal with the feelings of loneliness – both psychologically and by going out and meeting people. You have to adapt to your surroundings, you have to learn the language. But more than anything, it’s self-sufficiency; it’s proving to yourself that you’re going to be alright, that you’re not going to die. 

It’s really valuable, man. As for my favourite place in the world? That’s a really tough question and it’s probably a really boring answer, but I really love England. I love the English countryside; I love the city of Bath; I love London and I love Rio, where I am now.

You seem like an avid reader. Which three books have had the most profound impact on your life? At what age did you read them, and how did they change you?

I’ve got a theory that I’ve come up with about books. In almost every case, whether it’s spirituality or business, the first book that someone stumbles upon is the one that they consider to be the best; to have had the most profound impact on them. The reason is that if you don’t know anything about meditation and then you pick up Eckhart Tolle’s A New Earth or The Power of Now, your mind is going to be blown because you knew nothing on the topic. But if, instead, you picked up The Art of Silence, which is another spirituality book, your mind would also be blown.

But if you were to read A New Earth and then The Art of Silence, you’ve already had this huge influx of information from the first and a lot of that is going to be repeated in the latter – it doesn’t inspire the same epiphanies as you will have heard a lot of it before. So I have to preface my answer with that.

  1. A New Earth by Eckhart Tolle – I think it’s a very, very good book, and really beautifully clear and beautifully written. But I’m certain that if I’d read a different spirituality book before it, I would have preferred the other.
  2. The Four Hour Workweek by Tim Ferriss – I read that book at university when I was 19 and it opened my mind to what it meant to have a career. Even in terms of travel, that was a book that inspired me because Ferriss made travelling seem so easy.
  3. Pimp by Robert Beck/Iceberg Slim – It’s pretty dark reading at times; it’s about a violent, aggressive pimp. But it’s also a really beautifully written book, coming from an almost confessional perspective.

And then probably the book that changed the way I think the most:

“Surely You’re Joking, Mr. Feynman!” by Richard Feynman – It’s a book about the life of physicist Richard Feynman. It’s an absolutely amazing book – he teaches you how to think intelligently.

Then a book that kind of had a big effect on me, but not in any practical sense – it was almost in a spiritual sense:

The Universe in Your Hand by Christophe Galfard – It just explains the universe in a really easy way. It explains impossible physics in a way that you will understand. You have many experiences where you just look around you and you see the world in terms of the laws of physics that guide it.

Who are your role models or mentors, and what did you learn from them?

One thing that I’ve recognised more recently is the human capacity to believe entirely in one person. For example, you might find a role model and think they’ve got everything right, but then they say something that you fundamentally disagree with and there’s a tendency to question everything they’ve said up until that point. So all of the important and all of the amazing things that they said, we tend to throw away. 

I think we have to be careful in idolising role models. We have to think of them as being flawed individuals like everyone else; people who have certain areas of their life that we’re able to learn from, or certain capacities that we would like to hone in ourselves.

But, to be honest, Joe Rogan is a role model. He’s not this ‘guru-like’ figure. Most of the people that you see as prototypical role models always have this ‘guru-like’ factor. There’s always this sense of celebrity. Rogan is one of the few that has unbelievable power – literally to influence elections – and yet, he just says, like, “I’m a meathead comedian, I don’t know how the fuck I got here.”

Improving at anything is a process. What should guys be doing to improve the quality of their social and dating life?

You have to really want to. I think at some point, the pain of missed opportunities and the pain of laziness and procrastination becomes unbearable, to the point that the fear of approaching women is less painful than the pain of not approaching them. So I think there has to be a threshold there – but, for me, it manifested a little differently.

I didn’t feel like I was stagnating. I felt like I had stagnated. When I realised that it was possible to improve in this area, I had this feeling of like, “Fuck – all this time that I’ve wasted…” And then I thought about how beautiful it would be when I could talk to anyone, when women would be attracted to me. That was so thrilling.

You go from being unsocial to being cool and charismatic. But, in the end, you just love the connection; you love the thrill of the chase; you love being in the presence of beautiful women. Even that seems like a controversial thing to say nowadays, but that is a big part of it. Like, having facetime with beautiful women is pleasurable for heterosexual men.

For me, it was just an absolute commitment to fixing this area of my life. It was just like, there is no way that I’m not figuring this out.

Finally, what is your advice for young men?

My advice to young men is to figure out what you want to do. And I don’t mean like figure out what your life’s purpose is. I think that’s very difficult and mysterious and deconstructionist to figure out what the ultimate thing you want to do is. But figure out what you want to do on the surface. 

Do you want to make a bit of money? Do you want to get a bit bigger in the gym? Do you want to date a cute girl? I mean surface level goals. Because you can get lost thinking about what your purpose is and what you really want to do. Set some goals that you just want because you fucking want them – you don’t need another reason. And then focus on them.

Then figure out what you’re afraid to do. One of your goals might be travelling and you’re afraid to travel. But again, I would just say you’re never going to feel ready to do something you’re scared to do. You want to get a bit bigger in the gym, but you don’t know how to use the weights; you don’t know how to squat or do the form correctly and you think people are going to laugh at you – whatever. There’s going to be a fear attached to anything that you really want. You’re never going to feel ready to deal with that fear. 

So you have to plan doing that thing and then force your own hand. Go before you’re ready and then you just learn how to moderate fear and how to overcome fear.

And then everything gets better.