Three Character Traits Which Matter Most In Attracting Women

Dating and attracting women has undeniably become pretty hard these days. Particularly if you continue to rely on dating apps. But I see many guys complain about their dating woes yet fail at the three most fundamental things which make men attractive.

No, it’s not LMS — looks, money or status. Like I said in the previous article, they don’t matter much.

Of course, you should aim to achieve some basic standard on all three, but with most women, they make little difference once you’re simply not a slob. As for the women who do really care about those — I’d avoid them like the plague. Or like gold diggers. Or a lifetime of basic. Take your pick.

I can certainly tell you that LMS is not what played a pivotal role in my developing a great relationship and sex life. Instead, I found that there are three things which are sure to spark interest and land me dates.

And you can develop them, too.

The best thing is — these are no cheap tricks which might manipulate a girl into bed but likely end in hurt and disappointment, and show everybody how weak and flimsy your moral spine is.

These are about genuine self-improvement and becoming the sort of man women want to be around.

This is for you

First of all, let me be clear that no man should ever aim to become a better man for the sake of attracting women or because women tell him to. I know there are many women out there listing millions of requirements and men are sick and tired of feeling like they now need to tick all the boxes.

Don’t improve yourself for women. Don’t do it because society says you should. Don’t do it to fit anyone’s requirements or agenda.

Do it for yourself.

Photo by Usman Yousaf on Unsplash

Like philosophers from Plato and Aristotle to Friedrich Nietzsche and Soren Kierkegaard said, do it to:

  • become your best self
  • live a flourishing life of eudaimonía
  • become who you are — make your actual self match your ideal self
  • achieve authenticity and freedom

It’s not about what you do, it’s about who you are. Stop focusing on doing all you can to find dates, and focus instead on being the sort of person who dates find themselves.

Yes, it is going to take work

The world is full of guys who never push themselves to go further and refuse to improve because it’s ‘too much work’ and ‘the standards are impossible’. They tend to be miserable and blame everyone except themselves.

Yes, it is hard work. Grow the fuck up and get used to the fact that EVERYTHING WORTH ANYTHING TAKES WORK!

Life is not a never-ending TikTok feed of free dopamine, it’s not instant gratification of porn, and it has no cheat codes. You don’t get fit from taking a lift up a mountain, you get fit from putting on your goddamn hiking boots, strapping a backpack, and walking up, one foot after the other.

Hiking in Macedonia

This is literally one of the most amazing things about masculinity — the strength to get shit done, no matter what. To set a target and go. To stop whining and get on with it. To do things because they’re hard. To conquer fears and bring down walls. To push boundaries and defy limitations. To rise above difficulties, persist through adversity, and achieve greatness.

If you can’t be bothered doing any of that, if you prefer sitting and complaining, then you are an evolutionary dead end, living proof that the modern convenience culture is our undoing.

Honour your masculinity, take a long hard look in the mirror, and do what needs done.

Yes, you can make it easier

Having said that, let’s be real. If it’s too hard, we won’t do it.

BJ Fogg captured that in his book Tiny Habits, where he developed the following formula:

Behaviour change = Ability * Motivation * Prompt

In other words, there are three things which impact whether you succeed in changing your behaviour:

  1. How hard is it for you? Do you have the skill that matches the complexity of the task?
  2. How motivated are you? Do you want it real bad or is it not a huge priority?
  3. What reminds you about it? How likely are you to do it now rather than put it off indefinitely?

The idea is simple — you’re more likely to change your behaviour if you have the skill to do it, you’re highly motivated, and you have clear reminders.

Now, here comes the twist. Most people fail at the motivation part. Our motivation goes up and down, we start very motivated and then it goes away. Just think about the last time you resolved to go to the gym — went well for the first week and then?

The trick is to compensate for the fluctuating motivation with the other variables: increase your ability and get good prompts. Importantly, you increase your ability not by training hard — instead, you just make the tasks simpler so that you already have the ability to do them.

Below, I will follow this model and highlight exactly how you can make each task easier, what will prompt you to do it, and how to stay motivated.

OK, enough preliminaries. Let’s get into it.

Be chill

I know everyone says that the best way to attract a woman is to stop trying to attract women. And it’s true. But how do you do that?

Many guys are just desperate to pair up. They hate being lonely and feel they need someone to make their life complete. They miss the connection and want to feel wanted and desired.

This is very understandable — we all crave love and sexual frustration is a real thing. Both being underloved and underfucked has a massive influence on our mood and well-being. It’s no wonder some people are desperate to make it stop.

But the great majority of desperation doesn’t come from that. It comes from the external and internal pressures we willingly put ourselves under. The good news is, we all have the power to let go of them and be free to just chill out.

Check out of social expectations

The same rejection can happen to two people but it will crush one and the other will just shrug and move on. Why? Because the first one subscribes to a social narrative which says that attracting women and having a partner are oh-so-important. He thinks everyone expects it of him. He expects it of himself. And he can’t stand failing this expectation.

It’s the same as with anything else — whatever quest you’re on if you feel like the world depends on it and everyone is watching you, you’ll get stressed, tense, and probably mess up. This might even fly if you’re doing some more technical task because objects don’t notice you’re tense. But humans do. It makes them tense, the atmosphere gets dense, and you’re on a straight course for disaster.

image by EyeEm, Pixabay

Check out of this must-have-partner-now expectation.

Don’t hang out with people who have it and push it on you. Change the subject whenever it comes up. Speak out against people who shame others for being single.

If your family keeps asking you when are you finally going to find a girlfriend, have a serious conversation with them and tell them they are only making it harder. Don’t talk to them about it at all.

In particular — leave all the online spaces where this is all guys talk about because online anonymity brings out the worst in people. They will judge the living shit out of you and you know it. And even when you’re getting sympathy, it still grounds the idea that something is seriously wrong and needs fixing.

But the hardest thing to do is to challenge the expectations you have of yourself. We all internalise those social narratives. There is no easy path out of this one, but therapy definitely helps, as do many self-help techniques: meditation, journaling, practising gratitude, mindfulness… You can read around the topic and find what works for you.

What I personally find helps me a lot, is just a healthy dose of The Subtle Art of Not Giving a F*ck. If you generally don’t care much about social expectations where they don’t matter, you’ll find it easier to not care about them in dating.

Do I look like I give a f*ck?

You might never be able to fully get rid of this judging voice in your head, but if you can make it quieter, and especially if you can shut up all the other voices around you, you’ll go a long way.

Develop self-respect and a feeling of security

We are all sold this Rom-Com myth that we are halves of apples in search of our other half. It’s one of the most harmful things humans have ever done to themselves.

I think the sale of those things should be illegal

You are not a half of anything. You are the whole you. Why would you disrespect yourself by pretending otherwise?

So long as you go through life feeling like you need someone or something to complete you, you will never be happy. You’ll be constantly under pressure. Rejection will feel horrible because it’s an act of denying you something you need. How could you feel secure if you feel you’re lacking something vital?

But if you don’t? Whatever, you’ll be fine without. Sure, a relationship might make your life better, but there’s no pressure if it happens today or later. Many things would make your life better and you don’t fret about them so much, do you?

Remove those half-apple narratives from your life. Shut them down before they impact you. Don’t hang out with people who push them.

Do things which make you feel complete. Be financially independent, learn a skill, work on your body, start a business, practice mindfulness. Go on a solo holiday. Get in trouble and then save yourself.

Actively choose solitude. The difference between solitude and loneliness is like the difference between leaving your job and being fired. One you choose, one you don’t. One is empowering, the other depressing.

Be on your own intentionally. Choose to spend an evening in the great company of yourself. Don’t just make the lonely evening go away with a game or Netflix. Do something fun that makes you enjoy your own presence — a hobby, an art, reading a great book. Treat yourself to a solo dinner, cinema trip, massage, and do it with the mindset of: ‘I’m going to treat myself today.’

Slow down and chill the fuck out

Guys commonly treat attracting women like a race and get disheartened when they don’t see quick results. Our culture of instant gratification is not helping, and neither is porn which makes it seem like sex should come with no effort.

Taking it slow is always better. Most women are quite weary of men and the best way to relax the atmosphere and show that you are a safe, trustworthy person, is to intentionally slow things down. Don’t try to schedule a date as soon as possible. Don’t try to up the game until she obviously invites it.

Slow date with some tree-bark ships? Great for its own sake.

If you have the slightest sliver of doubt if she wants whatever you’re proposing, say it upfront: hey, I noticed you’re not super enthusiastic about this, so how about we leave it for now? Just give me a sign when you’re ready. Trust me, she’ll appreciate the hell out of it and you will grow massively in her eyes.

Maybe she’ll take this as an opportunity to pull out, in which case you’ll know that you saved both of you from making some bad decisions. Maybe she’ll come back in a few days feeling she can trust you and take things further. Either way, it’s a win.

But most importantly, if she chooses to come back, you’ll know she’s invested. She’s not doing it because you wanted it — she’s doing it because she wants to. Trust me, it’s worth passing on a hundred opportunities to find the one that will make you feel wanted.

So while you should naturally respect women’s autonomy and right to choose simply because it’s the morally right thing to do, there is also a personal reason to do it. Nothing feels sweeter than a woman’s genuine, free desire for you.

Having said all that, sadly we still live in a world in which most women will wait for you to make the first move and there is a danger you’ll miss your chance. I often feel that unless I do something, nothing will ever happen.

All who complain about how guys are too pushy should absolutely start by doing their fair share of initiating.

But the solution is not to push harder. The solution is to…

Flirt

Flirting is all about suggesting and inviting, not pushing. It’s about creating an atmosphere in which things could happen, but no pressure if they don’t. It’s about signalling you’re open to things without asking anyone to do those things.

Flirting is the best way to showcase that you’re chill and confident. It says: ‘We don’t need to, but it would be fun if we did.’

Learn to flirt. It’s the key to attracting women. It might be awkward at first, but it’s a skill like any other, you can practice and perfect it. Think of it like bantering with your friends, just throwing in some very mildly intimate details and compliments.

Talk about a trip you took with a friend but casually mention that she wasn’t half as gorgeously dressed as your date, and just move on without dropping a beat. Share some light-hearted secret, like an embarrassing moment from your childhood. Cheekily raise your eyebrow when anything she says could be a bit of an innuendo.

All of those are an invitation to play and you’ll quickly notice if she flirts back. As long as you keep flirting, you won’t miss your chance.

Be interesting

I have a personal rule. If I can’t spend an hour talking to a woman without dying of boredom, I don’t sleep with her. Not to even mention pursuing a relationship or even a friendship.

This rules out quite a lot of people. I wanted to say ‘unfortunately’, but actually, it’s pretty fortunate. It’s a good heuristic that helps me avoid getting bogged down in situations I will later regret. I don’t have the time to waste on someone who gets attached but brings nothing into my life. Not even if she’s hot, because without personality that actually gets old pretty quickly.

I know that many guys don’t think this way. But I am pretty sure that most women do. Correct me if I’m wrong, ladies.

If you live your life between a job and a game, if you struggle to answer when people ask you about your hobbies, if you never travelled much, if you dress the same way everyone does, if you take the most convenient path to every goal, if you’re way more likely to read about a thing than to do that thing, if you fill your free time with films, games or social media, if you haven’t tried anything new for months, if you’re not actively fighting for a cause you’re passionate about, if you don’t create anything — well, you’re probably not very exciting to meet.

This is the main reason women fall for bad boys — they might be bad, but they sure are exciting.

So here is a quick test for you, guys. Imagine yourself an hour into the first date. Is she looking at you with excitement for having met such an interesting person, or is she dying of boredom? It’s probably somewhere in between, but closer to which end?

If you’re worried you might be dangerously close to the bottom end of this scale, it’s probably time to look into becoming more interesting. Even if you think you’re at a healthy level, there’s probably something you could improve.

It requires stepping out of your comfort zone, but it’s really not that hard. Humans evolved to be natural novelty seekers — just lean into this and allow yourself to explore. You’ll need to give yourself a bit of a push to get started but once you do, it’s really fun. It’s a real win-win situation.

Try new things

First of all, you won’t know what are the things that could make you more interesting until you try them. It’s what we call ‘unknown unknowns’ — stuff you didn’t even know existed or never thought would be available for you.

I had no idea I could do acrobalance or fire spinning until I joined a performance group that did it. I always thought building human pyramids or running about with massive ball of fire were circus skills you needed years of training for. Turns out, a bunch of amateurs of all shapes, sizes and fitness levels can learn it all to a pretty decent level within a couple of months of training. It’s super fun and looks awesome.

Photos by the awesome Beltane Fire Society

Acrobatics doesn’t speak to you? There are a million things you could try. Some are obvious but you’ve probably never done them: fancy cooking, gardening, country cycling, ballroom dancing, playing an instrument, writing. Others are more adventurous: join a theatre group, brew your own beer, build furniture, get into fashion, become a toastmaster, play geocaching, sculpt in wood or clay, do wilderness survival, explore caves, train for an IronMan challenge, explore abandoned buildings, try tree or rock climbing, start blogging. And why not go for some sexy stuff while you’re at it: learn to do rope bondage, learn pole dancing, make your own sex toys, build fetish furniture.

Sounds daunting? I know! Here is how to make it easier and lower the stakes:

You know what’s best? Just checking out many new things already makes you interesting. But then, you’ll eventually find one or two you actually like and are good at. Pursue them. There’s nothing sexier than a guy who has a true passion.

Travel

When I finished my PhD, I went on a two-month solo travel around New Zealand, Indonesia and India. I had no plan other than pre-booked flights. It was like a passage ritual to me — take this spear and survive in a distant land. I didn’t have a spear. I had one small backpack and somewhat shaky knees.

I think this was the single best thing I’ve done for my confidence and becoming an interesting person. When I sat on the bus to the airport in Edinburgh, I was scared shitless and wanted to cancel it all. When I got back, I felt like I could do anything and had a hundred stories to prove it.

Sumatran rainforest, pretty big trees…

You don’t need to go that far. There is an infinite variety of options available and you can easily adjust them to your comfort zone, finances and ability.

But the way to adjust is not to stay well within your comfort zone. The aim is to be at the edge of it. Go somewhere that sounds just a bit challenging and scary but still doable. Maybe for you, it’s a weekend mountain hike. Maybe it’s the Carnival in Rio. Maybe it’s a month-long journey through India.

You can plan it in detail or go YOLO and hope for the best. You can go with people or do it solo. You can take an organised trip or plan it all yourself. You can pay for it or you can do it for free, hitchhiking, couchsurfing or volunteering.

The point is — experience new things and push yourself a bit. Next time, push yourself a bit more. And more. The further you go, the more you have to organise yourself and the less plan you have, the more likely it is you’ll come across things which will give you new ideas, expand your horizons, and make for amazing stories.

And give you way more confidence and faith in yourself.

Be critical of convenience culture

We have grown very accustomed to having it easy these days. You can travel without organising anything and never have to deal with the locals. You can buy everything you want with two clicks and get it delivered tomorrow. There is a service for everything and technology feeds you instant gratification with no effort.

Don’t you feel like something is lost along the way? Like taking a lift up a mountain isn’t exactly the same as putting your boots on and climbing it yourself?

Climbing Mount Olympus

You might know the notion of intentional hardship from David Goggins, Jordan Peterson or Tim Ferris, but philosophers have been talking about it for millennia. Across continents, times and cultures, Confucius, Socrates, Al-Ghazali, and countless others emphasized the importance of enduring hardships and practising self-discipline to cultivate virtue and moral character. Seneca and the Stoics were particularly big on this.

And probably your dad when he annoyed you saying that doing stuff you hate builds character.

Well, it does.

It also makes you interesting. Overcoming obstacles is interesting. You learn skills, work out solutions, and meet new people along the way. You see others do things differently and it gives you more ideas. You finish being proud of your achievement. You get inspired to do more. You start believing in yourself.

Boredom is one of the hardships you can pretty much never experience. The attention economy is predicated on taking as much of your attention as possible, leaving you with no time when you’re not consuming content.

But you know full well that your most interesting thoughts come when you’re in the shower.

You don’t notice interesting things on the way if you’re glued to your phone. You don’t come up with new stuff to do if you’re never lacking in pre-packaged, pre-delivered stuff. You don’t get original thoughts if you are constantly bombarded with other people’s thoughts.

Allow yourself to be bored, ideally every day. Don’t watch or listen to stuff while eating, cleaning or washing. Don’t take your phone with you if you don’t really need it. Let your thoughts wander and see where they go, because they will take you to interesting places.

Talk to people you disagree with

Another horrible thing modern technology has done to us is absolve us of the need to face ideas and people we disagree with. Social media close you in an echo chamber, feed you a distorted image of those who hold other views, and make it easy to discard them as stupid, evil, or both.

Photo by Afif Ramdhasuma on Unsplash

Being exposed to people with different views does four things to you:

  1. It broadens your horizons as at least sometimes those people have interesting things to say and you can learn from them
  2. It trains your logic and rhetoric skills as you defend your views
  3. It trains your emotional intelligence as you need to navigate the discussion in a way that avoids turning it into an argument
  4. It makes you more empathetic as you learn that the ‘others’ are actually quite all right

All of those make you more interesting as little by little you become a better debater with more nuanced perspectives, better communication skills, and an ability to see the best in others. What will help you get there?

Be generous, kind and altruistic

The Dalai Lama once said: If you want others to be happy, practice compassion. If you want to be happy, practice compassion. It sounds paradoxical, but study after study after study shows that the top thing you can do to make yourself happier is to stop thinking about yourself and start focusing on others.

Unfortunately, much of the Western world with its focus on individualism is telling us to put ourselves first. It’s a selfish culture we live in. And men who struggle with attracting women are rather prone to mostly think of themselves in this context.

But it’s not only that you’ll be happier if you become less self-centred — you will also be more attractive. Humans are social animals and we evolved to appreciate pro-social behaviour in others. Study after study after study shows that women find men who are pro-social to be more attractive.

Not to mention that if there is a single thing that pretty much all religions, philosophies and political systems agree on, it’s that being selfless and helping others is good. The way we judge narcissists, psychopaths and sociopaths, the very fact that we all tend to find excuses if we act in selfish ways, all show how little we think of those who are not pro-social.

If there is a single best thing you can do to promote your own well-being, attractiveness and reputation, it’s becoming more generous, kind, and altruistic.

And just to be clear, there is no faking it. Study after study after study shows that humans are pretty good at detecting genuine and fake altruism. Cheating won’t get you far.

Engage in pro-social projects, jobs, activism

Probably the best way to practice everyday altruism is to get a job where you genuinely work to make the world a better place. I’ve got this part cornered — I teach data ethics at a time when we desperately need to not screw up the world with AI, and write about masculinity at a time when so many men are struggling and need guidance.

Promoting my project at the University of Sheffield

But you don’t need to be a doctor, teacher, social worker, or firefighter. You can be an accountant, electrician or engineer, but work for a company or NGO which does something good for the world. You can be a CEO who prioritises people over profit. You can be a car mechanic, plumber or sales assistant who treats customers with honesty and respect.

And whatever your job is, you can choose to spend your free time on selfish hedonism of games, films or parties. On pursuing personal achievements in sports or hobbies. On only interacting with those who make you feel good.

Or you can choose to spend it on volunteering for your local community. Join an activist group fighting for a good cause. Organise events others will enjoy, run a self-improvement club, share skills with friends and strangers.

You can spend your expendable income on gadgets you don’t need, or you can use it to organise community events, support good causes, and pay a little extra for Fairtrade, organic products.

All of those signal you’re a good person and for all the attraction of bad boys, if you can combine being interesting and good, you’ll stand even better chances.

Treat people with respect and kindness

I know it’s fun to poke and troll people. It’s messed up how Nature gave us this weird feeling of joy when we see others fail. That feeling of power when we push others down.

Thankfully, Nature also gave us brains. They don’t develop fully until we’re about 26, but past that age, we should really appreciate that what makes a great man is not pushing others down and seeing them fail, but lifting others and supporting their growth.

The Guru I ment in Omkareshwar, India

This is the number one quality of a great leader: helping people put their talents to good use and flourish. Creating an atmosphere where people feel supported, respected and valued.

It’s an essential quality of a good partner because respecting each other as equals and lifting each other up are the cornerstones of lasting relationships.

It’s the building block of social life because one person’s respectful and kind attitude inspires others to be respectful and kind. The way you act not only comes back to you — it creates a culture that benefits everyone.

It’s best to think about this in terms of power. We all have some sort of power over others, ranging from CEOs who can determine how a company is run to an average Joe who can interact with people on social media. We can see it as power over others and use it to make others do what we want or just to see us as superior (introduce employee surveillance, bully or shame people on social media). We can see it as power to build and use it to inspire others to grow and do something good for the world (inspire supportive company culture, talk to and help friends who need it).

I don’t think I need to explain which is better and what she will find more promising in a potential partner.

Be (reasonably) generous with your time and resources

If you’re in a bar, buy a round. When a friend asks if anyone can help them move home, volunteer to help. If you’re part of a team project, be the first to take on some responsibilities. If you have a spare hour or two a week, volunteer it to a good cause.

Photo by Ullash Borah on Unsplash

Naturally, we all need to be careful with our time and resources and there are limits to how much we can offer. Those of us who have more can offer more. Either way, it’s important to know when to say ‘no’ before you exhaust yourself. But we can all do quite a lot before that moment comes.

Importantly, be generous whether people are watching or not. First of all, people are always watching. Secondly, we’re all pretty good at telling when someone is giving just for show. You’re fooling no one. Finally, generosity, like every other virtue, becomes a part of your character, so even invisible acts of it add up to who you are.

Being generous inspires others to be generous, and thus once again — you not only end up benefitting yourself, you also create a culture which benefits everyone.

Stop doing and start being

You’ll notice a common theme here. The tips are not about the specific things you can do, but about becoming a certain kind of man. A man who is relaxed, interesting, and giving.

It’s broadly inspired by the Aristotelian account of virtues as character traits you embody. You train virtues such as generosity, wisdom or confidence through actions, but the specific things you do are just a method of becoming a man of virtue.

Translated to the dating context, what makes you attractive is not the specific things you do — witty lines you say, clothes you wear, gifts you give, food you pay for. Instead, it’s who you are. If you are a confident, interesting and generous man, it’s going to shine through your actions without you trying.

This is where the ‘just be yourself’ advice starts making sense. If you’re desperate, boring and selfish, just being yourself isn’t going to attract anyone. But if you are a man of virtue, a relaxed, interesting and generous man, just being yourself is incredibly attractive.

But Simon! Women fail, too!

Yeah, I know. Some women are definitely also desperate, boring and selfish.

Hey, we live in times of increasing gender equality and women have proven time and again that they are perfectly capable of being just as shit and toxic as men. There, I said it.

Some of them do have impossible standards and they will always make you feel judged and less than. Some think they deserve a princess’s life by virtue of the glorious fact they have a vagina. Whatever!

Just ignore them. Let them complain how no man is good enough and die bitter and alone. You focus on the sensible ones.

And no, I am not going to write a text about women’s failings. My goal is to help men become better and I don’t think that complaining about women makes us better. End of story.

But Simon! You cheated!

This isn’t a piece about three easy ways to pick up chicks! It’s all about becoming a better man who is genuinely good company!

Well, yeah.

I said attracting women is about character traits which make you attractive. Turns out, being a great person who’s good company makes you attractive. Who would have suspected?

The bonus is — at the end, you become a genuinely better person. Because what, if you do it but not find a girlfriend, you’ll say: ‘what a waste of time, I’ve become confident, interesting and generous for nothing!’ ???

If you want a cheat sheet on how to get a girl in bed by Friday, bad luck. This guide is for guys who want something more than that. For guys who want to be genuinely attractive and build relationships that last.

And sure, it’s more work than a PUA cheat sheet. Like I said, tough shit. Everything worth anything takes work. I gave you some pointers on how to make it easier but at the end of the day, no pain no gain.

I can’t believe I’m saying this, but stop whining, be a man and get to work.



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