5 Mistakes That Keep You From Finding A Relationship

We talk a lot about what it takes to become someone that women want to date – working from the internal to the external, from attitude to presentation. But there’re times when it feels like you’re in a classic Red Queen’s Race: running as fast as you can and getting nowhere.

Sure, you’re putting in a lot of effort to get your presentation down and you’re trying to put yourself out there… so why isn’t it working?

Well the answer is that while you’ve made great strides in some areas, you’ve been neglecting others. In fact, many times, the problem is that you’ve been making mistakes that have actively hindered your ability to meet and date amazing women. What often confuses folks is that these aren’t mistakes that drive women away. Instead, these are mistakes that have hindered your personal development or your ability to connect with people in the way you need to forge a connection. These are foundational problems, ones that undermine both your self-image and your ability to meet and connect with people. You can tweak your style and grooming all you want, hit the gym until your joints give out or chat up as many sexy singles as you can… but if you haven’t fixed these common foundational mistakes, whatever you build is going to come tumbling down around you.

Let’s talk about how to fix some of the most common mistakes that are keeping you from meeting that special someone or someones.

You Don’t Hone Your Social Skills

If we’re talking about mistakes, then it’s a good idea to start with the basics… which is actually the problem. When people think of getting better at dating, they tend to focus on the “meeting women” part. This actually ends up being the source of many, if not most mistakes – something we’ll come back to a few times. But one area where it crops up the most often is how people who struggle with dating have prioritized flash over substance. This is, admittedly, entirely understandable. Flash gets people’s attention. Flash looks impressive as hell. But flash is fundamentally useless without substance to back it up.

This is never more true than when it comes to your social skills. Your ability to flirt, joke, tease or otherwise draw in women is predicated entirely on mastering the basics of social interaction, not the “cool” stuff. And very few people like hearing that.

Think of it this way: when you see trained martial artists in demonstrations and tournaments, your eyes are drawn to all the cool shit they do. Flying kicks, board and brick breaks, people jumping and flipping like Sony Chiba on a meth bender… it’s cool as hell. I mean, check this out:

This is legitimately impressive. As an athletic feat, it’s top notch, requiring a great deal of discipline, concentration, agility and practice. It’s about as close as humans are going to get to doing Ryu’s Tatsumaki Senpukyaku in real life. There is a lot of skill involved in this.

It’s also abso-fucking-lutely useless in anything other than a demo designed to look cool. You will never be in a position in where this will be even remotely practical to use in a fight. It’s 100% pure flash. But, even when making allowances for “you will never be called to use this unless you’re needing to kick a paralyzed dwarf, a man and Grog the Barbarian in the face in rapid secession”, it’s got a lot of what folks think of when they think of “cool martial arts stuff” – the jumping, spinning kicks, breaking boards and so on. That, plus “kick all the ass” forms the base of what many are looking for when they get into martial arts.

What folks often don’t realize – or like – is that this level of flash is only possible because the people performing it have a very deep well of substance behind it. Getting to the point that you can make that series of kicks requires mastering the fundamentals until they’re not just muscle memory but part of you. There’s a reason, for example, that people who study kendo or HEMA practice individual sword strikes over and over and over again. It’s a matter of drilling these very basic, very dull routines into you until you can do them reflexively.

So it is with people who want to get better with dating. The people who succeed the fastest are, paradoxically, the ones who are the least in the rush to get there.  The flash – sliding into the bar like Ryan Gosling – is appealing and eye-catching… but it only comes about when people have absolutely honed their social skills to a razor’s edge. Your social skills are the foundation upon which all social success is built. Your looks matter far, far less than simply being able to talk to people.

Now, notice very carefully that I said people, not women. This is where the disconnect tends to happen. One of the reasons why people often struggle is that they neglect working on the basics of social interaction. Even when they have put effort into practicing and developing their social skills, they’ve done so almost exclusively with an eye towards talking to women. And even then, they’ve usually focused either on women they’re attracted to…  or women they’re not intimidated by. And while there’s a lot to be said for learning how to not be intimidated by beautiful women, the problem is that, once again, they’re focusing on the flash.

The most socially successful men out there – the ones who are legitimate ladykillers, playboys, players, whatever label you want to apply to them – are folks who can talk to anyone. They practiced their social skills so that they could interact with everyone they encounter, not just the babe that caught their eye. Their ability to socialize with anyone and everyone is part of what makes them so successful, on many levels. It means that they don’t deal with approach anxiety, in no small part because they’re not worried about what to say or how to say it. They aren’t worried about approaching groups, because they know they can talk to men and women equally. Being a social guy is simply second nature to them… because they’ve mastered the basics first.

Don’t get me wrong: this doesn’t mean you need to be a gregarious social butterfly in order to date. But if you’re someone who struggles with dating, then often what you need to do is focus on being able to strike up conversations with people – not women, people. Young and old, hot or not, guys, gals and non-binary pals, being able to be social with anyone is vital. This means that if you’re going to, say, practice starting conversations with strangers, you can’t just focus on cute women. This tends to be a great way to leave yourself feeling too intimidated to deal with men – whether it’s a mixed group at the bar, her guy friends or even just broadening your social circle.

Similarly, you don’t want to only focus on trying to pick people up. Most relationships and dates don’t come from cold-approach situations – people tend to meet their dates through friends or shared activities and interests. Even online dating requires functional social skills – matching is just the start after all; you need to be able to keep up your end of the conversation, both online and in person.

Now the good news is: this is easy enough to fix. Social skills are skills and improve with use. Making a point of taking opportunities to have brief conversations with people – in line for coffee, at lunch, and so on – is not that big of a lift. It’s just a matter of being willing to focus on the less-sexy fundamentals.

But the good news is: the basics may not be sexy… but they’re what make the sexy parts possible.

You’re Waiting For Someone Else To Do the Work

Here’s another common problem that people struggle with: they want someone else to do the work for them. This can manifest in many ways – from wanting women to approach more to refusing to say anything unless they’ve been given the 100% unmistakable green light – but it all comes down to the same issue: they don’t want to take responsibility for their choices.

Now, for the sake of brevity, let’s take a common example: when and how to approach someone and strike up a conversation. This can be intimidating, especially if, say, you’ve neglected your social skills. However, there’s “intimidating and slightly scary” and then there’s “well, I didn’t get someone waving me in like I was doing a carrier landing so I’m not gonna bother.”

The issue at hand is less that talking to an attractive stranger is intimidating and more that what folks end up asking for is a reverse pick-up. That is, they want that sexy stranger to clear the path for them and walk them through the steps of how to pick them up. From complaining about a lack of approach invitations to framing it in concerns about being “creepy”, what they are ultimately looking for is a way to meet women with minimal investment and even less risk. If they have less than 100% of a chance of being guaranteed a date by the end of this, they don’t want to bother.

Ultimately, this comes down to a fear of rejection – often equating rejections with increasingly overblown consequences, up to and including “being thrown out of the bar” and “sued for harassment”. Many will justify their fears by pointing to stories on subreddits or viral TikToks of women complaining about men’s audacity. Rather than taking the risk of being the next West Elm Caleb (somehow), they’d rather wait until they can be sure that their interest is welcomed.

So they wait.

And wait.

And wait some more.

The same is often true with how people will go about managing their relationships. Sure, they got the date, but every other aspect of the relationship has been dictated by their partner… by default. Rather than advocate for their needs or interests, they’ve functionally turned the care, maintenance and progression of their relationship over to someone else. They’re simply unable or unwilling to take a stand or take responsibility and so let someone else call the shots. All the shots. They’ve taken the position of being the silent partner, only with even less of an investment than the title would imply.

As a result, they have become entirely passive in the relationship – frequently leaving their partners angry and frustrated that they have to manage the life and emotions of two people, rather than having a proper partner who’s an equal participant. This, incidentally, includes folks who want to break up but don’t want to be the one to do the dumping. Instead, they become increasingly distant and uninvolved until their partner finally pulls the trigger themselves.

While there are valid discussions about gendered roles within dating – even within same-sex relationships – the truth is that too many folks are afraid of putting themselves out there. But rather than own that they’re afraid of the potential consequences, however overblown, they frame it in passive or misleading language. What they’re ultimately hoping for is a frictionless and effortless experience that requires minimal risk from them. But the truth is that there is no reward without risk; you can’t get the fruit if you aren’t willing to climb the tree. Worse, avoiding these uncomfortable situations only makes those fears worse.

Relationships are never passive, from start to finish; they, by their nature, require participation from all involved parties. Expecting one or the other to do the lion’s share of the work is a great way to ensure that you aren’t going to have one… certainly not for long.

In fact, while we’re on the subject…

You Don’t Make Room In Your Life For a Partner

Here’s a question I ask all my clients who struggle with meeting women: how, precisely, will your life change if you had a girlfriend?

Not in the sense of “well, now I’ll actually have someone to have sex with”, but what adjustments are you going to make to your day to day life once you have a girlfriend.

This is something that comes up more often than you would think. When I said that people tend to focus too much on meeting women and not enough on what comes after, this is a prime example. It’s the classic case of dogs chasing cars; they don’t know what they’d do if they actually caught one. The same is true with dating – many folks have put little to no thought into just how a partner would fit into their lives.

All too often I’ve heard from people, mostly but not exclusively women, whose partners seemed to not realize that they were going to have to make changes to their daily lives to make a relationship work. As client told me: “It’s like he just thought I’d be available for sex when he wanted and otherwise just off in another room until he wanted something from me.” Another found that she was coming in second (and often third) to his gaming schedule. “It’s like he thought getting a girlfriend meant I’d sit on the couch with him while he played Destiny or Fortnite until he wanted to do something else.”

It’s not that these guys were self-centered or didn’t care about their girlfriends; they never thought past the “get a girlfriend” part. Because they had never considered how a relationship would change their lives, they had a large blank spot in their idea of what life with a girlfriend would be like. Quite frankly, there they just assumed that she would somehow slot seamlessly into their lives.

Now, it’s easy to joke that this is just a virgin problem and that only people who’ve never dated before deal with this. But the truth of the matter is that it’s far more common than people realize. Plenty of people want to date, but have structured their lives in such a way that makes it incredibly difficult to maintain a relationship. Many men in their early to mid 20s, for example, tend to be hyper-focused on their education or careers – they’re too set on the grind of trying to establish themselves, and so they have neither the bandwidth nor the free time to date. Others  pack their schedules to the point that there is no wiggle-room. In order to have time to date, they’ll have to give less time to another activity – what’s known as the opportunity cost.

The opportunity cost is a factor in everything in life. There’re only 24 hours in the day, so anything you do comes at the expense of other things. Going on dates and spending time with a partner is going to take time away from other aspects of your life, aspects that may be important to you. You have to decide where your priorities lie, and what you are willing to give up in order to make room for a partner. Sometimes this means gaming or other hobbies. Other times this means spending time with friends or putting in overtime at work. Or you may get up earlier or go to bed later in order to have more time to fit those activities in. But it’s important to recognize that making those choices is about choosing what’s most important to you.

Having a relationship is a balancing act. You have to balance your life and interests against time with your partner, same as they do. In the early days, this is easy. During the honeymoon phase, you and your new honey are inseparable (and often insufferable). This is the time when the dopamine and oxytocin are surging and you never want to be apart. In fact, this is why people will often say that friendships fall apart when someone gets a girlfriend; suddenly they’re spending all of their free time with their sweetie instead of their friends. But the honeymoon phase always ends, and that’s where it gets more difficult to decide where to spend your limited time.

Now to be absolutely clear: this doesn’t mean that dating means that you have to give up on things that you love. It simply means that you need to weigh what matters to you and decide if or how to shuffle them around to make room. Nor does this mean that your partner needs the lion’s share of your time. After all, while a relationship may be a gestalt of two (or more) people, you don’t stop having individual needs, including space within a relationship. Some couples only see each other a few times a week. Others may live together, but spend time apart to pursue their own interests. Being in a relationship just means that you have to consider someone else’s needs and interests along with your own.

But if  you don’t have any room in your life for a relationship and you aren’t willing to make room, you will have undercut any chances of actually dating someone.

No matter how much you may want to.

While we’re on the subject though…

You’re Expecting A Relationship to Change You

This mistake is an insidious one, because people don’t realize they’re making it.

People who are making this mistake often date and even have relationships. However these relationships are… well, calling them “turbulent” is often an understatement. The people who make this mistake the most are prone to dating “the wrong people”, partners who seem great or exciting but who fit them like a pair of shoes that’re too small.

Contrary to popular opinion – and early 90s pop singles – opposites don’t, in fact, attract. We, as a species, tend to prefer people who are similar to us; the more commonalities we share, the more we find ourselves drawn to them. However, this doesn’t stop folks from dating people who are profoundly unlike them. Often with completely predictable results.

If opposites don’t attract, then what drew those couples together in the first place? Well, often, the desire to be someone else.

No. Seriously. There are many, many people who believe a relationship will make them a different person, and so they date someone who has the qualities they feel that they’re missing. Someone who’s staid or unadventurous may date someone who’s more of a wild child because they want to feel more exciting. Someone who’s more straight-laced may date someone who’s more unconventional because they feel like they’re boring and want permission to cut loose. In short, they want the Manic Pixie Dream Girlfriend Experience, where someone sees their potential, takes them by the hand and teaches them how to be as unlike themselves as possible. With blowjobs.

The problem, of course, is that this doesn’t actually work. Not only do Manic Pixie Dream Girls not exist outside of the fevered imaginations of certain screenwriters, but dating isn’t magic and sex isn’t alchemy. What often ends up happening instead is that any initial physical chemistry they may have overshadows the deep incompatibilities they have. The wild child gets frustrated with how dull the straight-laced dude is, while he gets bothered by how much she disrupts his calm and ordered life. The shy guy feels overwhelmed by the outgoing extrovert while she gets tired of constantly having to drag him out of his shell.

Worse, however, are the folks who think that the fact that they’re dating someone – anyone – will change them for the better. The most common example of this are people who think that a relationship will make them more confident and self-assured. And to be sure: it does… very briefly. However, the high always fades, and the comedown is murder.

The good times can never last. When the high recedes, the self-esteem boost has not only vanished, but has often left them feeling even less confident. This is often when doubts and anxieties will creep in. People who think that dating will fix their confidence issues end up plagued with suspicion and doubt. After all, why would someone that awesome date them? Isn’t there a chance that someone even better is going to come along and snatch them up? Or, worse, she’ll leave, having realized that she made a huge mistake being with him.

Because his self-esteem is based on someone else’s approval, it’s inherently fragile. If her opinion were to change for any reason, then the whole structure will collapse like a house of cards. But the break-up is often inevitable precisely because he can’t feel secure; the insecurity needles at him and his anxieties and need for reassurance end up pushing her away. The calls are coming from inside the house, as it were.

There are even those who think that a relationship – any relationship – will unlock a secret side of them. They see themselves going on spontaneous road trips or cooking romantic meals together or taking trips to exotic lands in search of adventure and excitement. They merely need someone to awaken this side of themselves that must surely exist. Except… it doesn’t. It never has, and the proof is that they haven’t done any of those things already. If they weren’t already an impetuous person or someone who already took exotic trips, they would already be doing so.

The fantasy of the transformative relationship is just that: a fantasy. It’s a belief about who they think they should be, not who they are, and nobody, no matter how wonderful, is going to create those personality traits if they weren’t there already. At best, all that would happen is a momentary burst of enthusiasm, followed by reality setting in as they realize how disruptive that road trip would be or how “adventure” tends to translate to “lack of amenities and creature comforts”.

To be sure, plenty of people have been inspired, even motivated, by their partners. But this has far less to do with any transformative power of love and everything to do with getting a boot-to-ass to do the thing instead of just talking about it. If you’re going into a relationship, you have to understand that you’re going to come out the other side as the person you were before. Maybe you will be a more polished version, or maybe you will have changed due to the same growth that we all go through. But dating someone won’t make you a different person, nor do women want to invest time in a fixer-upper.

Relationships aren’t self-improvement programs; they’re relationships. Expecting a transformative experience is, at best, a recipe for disappointment. At worst, it’s an invitation to date people who are radically wrong for you or who’re willing to take advantage of your naivete. If you’re going to date someone, date them for who they are and who you are, not who you think it’ll turn you into.

And finally

You Believe the Worst… About Everyone

OK, so we’ve saved the worst for last. But it’s also one that comes up the most often – including here.

Every relationship is an act of trust and vulnerability. If you’re going to date someone you are, by definition, opening yourself up to the potential to be hurt. For many people, taking that chance is just a leap too far. Not only are they are they not willing to accept that risk, but they believe that it’s a matter of time until someone would exploit that vulnerability to hurt them.

Why? Because fuck you, that’s why.

If that doesn’t make sense to you, it’s because you aren’t convinced that the people you want to date are the worst people ever. As are the people they would want to date. And your friends, family, and… well, pretty much everyone else, really.

The origins of this belief tend to be variable. For some, the inciting event was something that happened in their past, most often in junior high or high school. This is a time when kids are at their most cruel; the mix of surging hormones, the ebb and flow of social status and authority-sanctioned targeting of the “different” was bad enough. The addition of “ironic” antisemitism, racism, homophobia and transphobia on chan-sites, algorithm-powered abuse and disguising bullying with social justice terminology just pours gas on an  already a raging fire of bullshit, encouraging people to be at their worst for clout. For others, it comes about from listening to people who’ve so much as talked to a woman explain at length what men and women “really” want.  For still others, it’s a case of  brainweasels, hopping on the anxiety button like a toddler given a double-espresso and promised a free puppy.

Regardless of the origin, the results are the same: the bone-deep belief that people couldn’t possibly like you or find you attractive. Worse, the folks who seem to like you must be lying. They’re dating you out of pity, or in the name of some scam. What that scam could possibly be is a mystery but usually involves either cuckoldry, financial fuckery or both.

This is, needless to say, a great way to smother any potential relationship in its crib. Relationships are, after all, built on trust. If you can’t trust your partner when they tell you that they want you, love you or need you, then your relationship is on borrowed time. You can only call your lover a liar so many times before they will quit trying to convince you that they’re telling you the truth. Worse, though, is that these beliefs imply how little you think of people in general.

To start with, this mandates a belief that women are a hive-mind, who are all exactly the same regardless of age, orientation, culture or ethnicity. All women everywhere require high-value men and value the exact same things – even when folks can’t agree on what makes someone high-value. It requires that you believe – truly believe – that women are simply shallow and vapid, either incapable of seeing beyond the surface or unable to have a relationship that’s based on love, trust, shared experiences and values.

(It also means that when women do decide to “settle”, they’re doing so solely in the name of financial support, regardless of how much money they’re making on their own. So they’re willing to condemn themselves to a life with someone they don’t love and have sex they don’t like, purely for money. Which… says a lot about what those people think about women and sex work, really.)

It also means believing the worst about yourself. This outlook requires that you not only believe that no one could nobody possibly love you – and that believing they could is just a delusion – but that change is impossible. You can’t possibly reach the level required to get women’s attention, never mind their approval. If you were able to somehow break through that level cap, women would still be able to detect the failure on you and not waste their spit on you if you were on fire.

Now needless to say, this is easily disprovable. It takes next to no effort to debunk; you just have to go to a Walmart or Costco on any given weekend to see folks who are less than model-fit with their girlfriends, wives and kids. And while the truly dedicated will insist that these are all just betas raising someone else’s kids like cuckoos in the nest… ultimately logic doesn’t come into it. It’s pure, uncut anxiety and a sense of not measuring up to an arbitrary and in many cases literally impossible standard and one that most of the people they want to date even give a shit about.

This mistake, needless to say, is one of the most pernicious. It survives, not because it makes sense, but because it taps into the negativity bias inherent in all people. It’s easy to believe the worst about others when it also confirms your worst anxieties. If you already doubt how people could possibly like you, it’s barely any effort at all to buy into the idea that it’s a universal condition that excludes you, specifically. But at the same time, it requires your not thinking about it too hard; the point isn’t to prove it to others, it’s to avoid having it disproven to yourself. After all, if the issue is that you can’t match other people’s standards and people who say they like you are just lying, then there’s no point to hope. There’s certainly no point to trying to do anything about it.

But here’s the thing: most folks don’t believe and don’t want to believe it. They are afraid it’s true and will accept its validity because it makes ‘sense’. But what they want, more than anything else, is to be wrong. There’re always some who want to spread the bad news, sure; if they can convince other people, then they’re justified in not ever bothering to try to do better. But everyone else? They’re looking for any shred of hope, even as they fear to let themselves feel it.

If they didn’t believe that they were wrong, they wouldn’t keep trying.

Now, this one is hard to shake. It’s an inherently self-fulfilling prophecy; if you don’t believe others could like you, then you’re going to miss more opportunities, you’re not going to work as hard when you do find them, and your setbacks will be that much harder to recover from. But it’s a belief that, if you can cling to the slightest sliver of hope, cling to it with your teeth like a pitbull, you can pull out of.

The first step is simple: you have to accept that you could be wrong about all of it – men and women and especially about yourself. If you leave even that much of a crack, then the hope can get in. You have to hold fast to it, so you can start to allow yourself to trust. Maybe it will be a friend, a family member or just some loudmouth on the Internet… but someone will say the words in a way that’ll actually stick. They won’t embed themselves deeply enough to root out the belief by itself, but it’ll be a start. Those words create more doubt, build a little more belief in yourself, which lets you challenge those negative beliefs. If you could be wrong in this small way, what else could you be wrong about?

Yeah, you can’t just doubt your way out of this, any more than other people can love you out of it. But if you can doubt your belief and trust others, you can accept love. If you can accept love from others, you can love yourself. And if you can love yourself, you can fight. That fight can be hard, seemingly impossible. You may need to summon friends to help fight back the demons or get professional help from a trained counselor or therapist. But that’s ok. That’s what they’re there for. Letting other people help is a sign of strength.

But the good news is that each belief makes the next that much easier to accept. Each time you’re willing to believe a little better – about yourself, about others – you become a little stronger, you’re able to hold on that much tighter and dream a little longer. And when you finally let go of this belief, it will feel like tossing aside a massive weight, one that you didn’t realize you were carrying. It’s not easy, but nobody said it would be.

They just said it would be worth it.