This is How You Solve Your Dating Problems

This is How You Solve Your Dating Problems

It doesn’t matter who you are, what you do, or what you look like; at some point your love life is going to go pear-shaped – quite possibly messily and all over the place. Sometimes it may only be for a few days or weeks. Other times, you end up in a dry spell that could last for months or even years.

“How… how long has it been? Time passes so strangely here in the desert of the dateless.”
“It’s been two days, Bob.
“An eternity… an eternity…”

The frustration is understandable, even palpable. Many times, you don’t even know why you’re suddenly having all of these problems. It’s bad enough to be having a dry spell or to be struggling to date when you can’t even figure out what you’re doing wrong. Everyone’s had that frustrating moment of asking their friends what they should do, only to be met with a shrug. Worse, the only advice they may have for you feels less than useless or seemingly impossible to follow.

It’s understandable that many would give up; after all, how do you fix things when you don’t know where to start? What’s the dating equivalent of debugging your love life and can it be as simple as just turning it off and back on again?

Here’s how you can find your sticking points, fix your flaws and get your love life back on track.

When In Doubt, Write It Out

The first, and possibly most important part of fixing your stalled love life is to gather information. After all, you can’t solve a problem if you can’t identify where the problem is. And while it’s all too easy to throw your hands up and say “clearly, it’s just me”, the truth is that most dating problems are rarely mysteries. The issue at hand is that we rarely have the distance, perspective or even the data to properly see where things are going wrong.

This is why when you’re stuck, you need to gather information. And to do that, you need to write it out. All of it.

Yes, it’s time to embrace journaling. Keeping a diary will make you a better lover…

male hand writing in notebook with pen
“Alright, got my Moleskein, got my EDC pen collection, gonna be a memetic sex god…”

…just not in the way you may think.


male hand writing in notebook with pen
“Well, shit.


Here’s the issue: despite what we often assume, we’re not the objective, dispassionate observers of reality, especially our own. Human memory is notoriously unreliable, and self-awareness is not only rare, but tends to come with significant blind-spots. We are especially bad at recalling or  accurately gauging how much effort we’ve put into something, how much time we’ve invested or even how many times we do something. We tend to guess and estimate, and we tend to guess wrong – either vastly over or under-estimating just how much we’ve done. These blindspots and inaccurate guestimations show up all over the place, from hours actually worked, to what we eat, or even how physically active we are.

Worse, the more something gets tangled up with our egos and self-worth, the more we tend to over-estimate and exaggerate. At first, those overstatements may be hyperbole for effect, but before long, they become the factual basis for the narrative we tell ourselves. We may start out saying, for example, that we have hit on or approached or messaged all  the available women in our city or on the apps in a way to emphasize just how much we’ve tried. However, the longer we tell that story, the more we tend to act as though it were literally true – that we really must have struck out with every potential match in a major metropolitan area.

This is why writing things out is vital. If you want to change and make changes that stick, then you need something you don’t have: actual data. What you’re doing is keeping actual records of your activity (or lack thereof); having that information on hand makes it possible to track things with increased accuracy. Having an actual running account of your activity, with dates, numbers and assorted other quantifiable information makes it that much easier to measure your progress and zero in on where you’re having problems.

What you need is to keep track of your activities when it comes to dating. This means keeping as detailed records as you can manage, tracking who you talked to, how, what you said, how you felt and so on. If you’re going out and making cold approaches at bars or clubs, for example, how many people did you approach? What nights were you going out, what time and where did you go? How did your mood and your energy change over the night; when did you feel at your best and when did you feel at your worst? What were your results? How many times did you get a phone number or a date, how long did the conversations last and what were the results?

If you’re working on building your social skills, then you want to track things like how many times you’re going out and where, how many people you’re talking to and for how long, and so on.

Do your best to avoid editorializing or assuming that you know what other people were thinking or feeling; these require information that you don’t actually have. While it’s impossible to be completely objective, you want to stick to the concrete facts as best you can instead of making guesses. You don’t know why someone rejected you, you just know that it happened. Everything else is just a guess – possibly an educated guess, but still just a guess.

Business man wearing a dunce cap sitting on a stool with his back to the camera and facing a wall
… and we all know the state of the education system these days.

The key is to focus on things that are measurable and are actually within your control. Since you can’t control somebody else’s moods, feelings or the day they’ve been having, speculating is less than useless. Similarly, the inherent negativity bias we all have means that we’re prone to assuming the worst, especially about things we’re insecure about. So focus strictly on things that you have direct agency over; it’s the only thing you can change, therefore it’s what you should measure.

Ideally, you want a system that allows you to skim the information quickly, track changes accurately and lets you grasp the overall trends at a glance. For best results, you want a tracking system that works for you, even if it’s complete gobbledygook to anyone else. If you find that bullet-journaling works best for you, then by all means, use that system to keep track. Spreadsheets may work better for someone else, and writing things out work best for still others. If you’re more visually oriented, it may help to have a system of graphs or other forms of data visualization. You may want to consider additional information like adding pictures of yourself in the outfit you were wearing for each particular day and notes on how those clothes made you feel.

Similarly, keep tabs on related facts, like where you’re going and how comfortable or uncomfortable you are in those places.

What you’re looking for are patterns of data that tell a story – especially when the data contradicts the story you’re telling yourself. Are you really practicing as much as you say? Are you really not making any progress, or is it just that you haven’t noticed how much progress you’re making? Similarly, you’re looking for repeating patterns and commonalities. Are you always going to the same places, especially places where you may feel like you don’t fit in? Are you using the same lines? How do you feel? Are you experiencing the same moods when you go out?

Keep in mind: not everything is going to break down to numbers or is easily quantifiable as a mathematical equation. Not everything can be reduced to pure data, nor is it supposed to. You don’t want to dismiss things like mood tracking, for example,  just because they seem fuzzy or that they don’t break down to math. Keeping track of how you’re feeling and when can help you find triggers that are sabotaging your self-esteem and draining your motivation. When you can see that you have, say, clusters data that says your mood drops correlate with certain events or locales, you are more likely to zero in on a sticking point.

This is the value of keeping data and looking for patterns; the more information you have, the greater the odds of zeroing in on just why you’re stuck. It’s about figuring out where to start looking for problems. Once you have that information, you’re in a much better place to actually fix things.

To Get Different Results, You Need to Do Things Differently

The next step is one of the most difficult ones: once you’ve started identifying potential sticking points, you need to address them. And a lot of folks, quite frankly, don’t want to.

One of the most frustrating things to hear from folks who are chronically stuck is how little they’re willing to actually change. All too often, you’ll hear folks say things like “well it should work!” or “I don’t see why I should change to make other people like me more.” Or you might hear “It’s what I know” or “I’m not the kind of guy who does X,”

Angry middle aged man in a blue hat pointing index fingers at camera
“No, no more. Not one more step. I have changed enough for those fickle females. THE LINE! MUST! BE! DRAWN! HERE!”

OK, so you aren’t the kind of guy who does X or Y. Cool. So… how’s that been working out for you, so far?

Here’s the hard truth: when things aren’t going the way you want, you have two choices: you can either change the circumstances, or you can change how you feel about it, but either way you have to make a change. If what you’re doing – or not doing, for that matter – hasn’t been working, for the last 100 times, it’s not going to magically start working the 101st time. Similarly, just because something may have worked for you before doesn’t mean that sticking with it is the answer and you don’t need to change. If something that worked in the past isn’t working now, that’s a sign that circumstances have likely changed and you need to change with them. As the old saying goes: doing something the same way over and over again and expecting different results is the path to frustration and bitterness.

This is important to keep in mind because one common reason why folks get stuck is because they don’t want to do things differently – even when they’re unhappy with what they’re getting. In a very real way, this stubborn resistance to change is a matter of self-defense; it’s a way of preserving your ego by implying that changes would be impossible or are unreasonable to ask for.

Someone who insists that they can’t do anything differently because they’re so ugly that it wouldn’t make a difference, for example, is someone who’s trying to avoid making changes. Yes, their excuse for not changing may be negative and insulting about themselves… but it’s still a form of ego protection. It implies that the issue is out of their hands and impossible to change, rather than accepting that they have a hand in their own lives. Hence, you’ll have folks who react with anger when you make even the slightest suggestion that they change their behavior or outlook.

Case in point: many folks reading this part will say “Oh I see; I just need to be a different person entirely, gotcha.” And… well, yes. You need to be someone who does things differently, and thus far, you aren’t. The fact you’re stuck is a pretty strong indicator that what you’re doing isn’t working. After all, if it was, we wouldn’t be having this conversation. Much like when a car is stuck in the mud, just revving the engine and trying to drive forward isn’t gonna set things free. Doing more of the things that got you stuck in the first place aren’t going to set you free.

That unwillingness to adapt or accept your own responsibility is one of the things holding you back. Framing your sticking points as aspects that are outside of your control – your facial features, your height, how much hair you do or don’t have – are excuses to avoid change and responsibility. People who aren’t conventionally beautiful date, short people get married and balding folks have plenty of sex. But even if it were true that your problems were entirely due to, say, women being too picky, then you’re right back to “you can change the circumstances, or you can change how you feel about them.” Do you really believe women only date guys built like Marvel superheroes? Well, complaining about it isn’t gonna change anything, so you either better get in the gym or figure out what you’re going to do instead.

Meme of two musclebound characters from Full Metal Alchemist shaking hands. Text reads: "What do we do with our feelings? We hide them in our muscles. How do we hide our feelings better? We get bigger muscles"
Why do you think I’m so swole?

It’s worth noting that one reason why people get stuck or refuse to do things differently is because they’re too entrenched into their comfort zone. It is one thing to know where you’re most comfortable and secure; it’s another entirely to never leave, especially when your comfort zone is what’s making you miserable.

Angry middle aged man in a blue hat pointing index fingers at camera

Unfortunately, your comfort zone is a poor basis for comparison and a worse judge for what does and doesn’t work for you. Discomfort may be unpleasant, but that doesn’t mean that it’s bad. When you’re not used to treating yourself like you matter, loving yourself can feel like arrogance. Addressing your presentation can feel like vanity and actually going for what you want can feel like you’re being presumptive and aggressive. It’s not; you’re just unused to showing up for yourself.

Journaling and tracking your information helps you zero in on sticking points and identify places where you may need to change. However, you need to actually make those changes and sustain them to actually make progress. You can’t just try something once and declare it a failure. Most folks fail to improve because they quit before they’ve had a chance to see any results from the changes that they’ve made. If you want to see real progress, you need to give those changes time to actually take effect. If you expect instant results – or if you think you need to succeed the very first time you do something – you’re only going to disappoint yourself and undercut your own progress.

As a general rule, the things that most often need to change are, in order: your attitude and behavior, your style and presentation and then your technique. Most of the time, people’s sticking points tend to be internal rather than external. That is: it’s often more about how they feel about themselves and others than it is about knowing exactly what to do or what to say. Ted Lasso’s Jaime Tartt, for example was a skilled footballer, but he was a self-absorbed prick and it was wrecking both team unity and his own life. He didn’t need better skills, he needed to learn to be less of an egotistical showboat and how to be a better teammate and a better man.

screenshot of actor Phil Dunster as Jaime Tartt, confronting his father in the Richmond locker room
…but seriously the headband and eyebrow thing have to go. YOU GET ONE, JAIME, NOT BOTH.

It’s also worth noting that sometimes what you need to look at is who you’re trying to date, rather than how you’re trying to meet them. Many times, people get stuck because they’re pursuing people who aren’t right for them. You can be the most charming, sophisticated and suave motherfucker in the room and none of it’s going to matter if the person you’re trying to get with is fundamentally incompatible with you.

Sometimes the change you need to make is what you’re looking for and why. That’s not giving up or “lowering your standards”; it’s personal growth.

Make Sure You’re Trying to Solve The Right Problem

Let’s talk about another common stumbling block people face when they try to fix their dating lives: they spend too much time fixing the wrong problem. Or, rather, they’re spending too much time on things that aren’t actually problems.

You have undoubtedly heard of The Pareto Principle – the idea that 80% of consequences are the result of about 20% of causes. While this is often wildly misunderstood and misapplied when it comes to dating, it does hold true in one critical area: people focus far too much on the 80% of effort that doesn’t supply an equivalent level of results. It’s the social equivalent of body building over functional strength; your biceps may be big flashy muscle, but your core and legs do most of the actual work. In dating – especially when it comes to social skills and meeting women – people often get hung up on the flash and miss the substance.

The emphasis PUAs used to put on “peacocking” or dressing in an unusual but eye-catching way is a prime example. Dressing up in outlandish outfits was supposedly proof of your confidence and self-assurance and would signal your value to others. In practice… mostly it made you look like an idiot. There’s a reason why Mystery is more famous for goggles and fuzzy hats than, y’know, being the last of the Red Hot Lovers.

Screenshot from VH1's The Pick-Up Artist. Matador, wearing a mesh shirt and jeans, stands next to Mystery wearing a beanie, goggles and brocade coat in the center, wtih a blonde woman in red on the right
The whole “gear doesn’t match but gives amazing  stat bonuses” thing doesn’t track outside of Destiny and Final Fantasy XIV, sorry…

Most of the time, we tend to assume things are important or vital based more on flash than on substance. They’re the things we find impressive and thus must be effective when, in reality, the subtler, less showy behavior is what gets the goods. You can make a fuss about how amazing your Maybach is, but that’s not going to actually translate to “getting more dates”. At best, you’re going to find someone who’s only interest in you is your car, not you.

The issue at hand is that many times, when we find ourselves stuck and our dating life has stalled out, we’re usually just guessing as to why. We zero in on causes based on assumptions and bad information about, say, what women want in a man, rather than on reality. Other times we may have the right problem but the wrong reason for it.

A common – and frequently recurring – example would be approach anxiety and a fear of being labeled a creeper. If we take a step back and look at the situation critically, it becomes clear how much this is about how you feel about yourself, rather than technique, tactics or timing. The issue that needs fixing isn’t finding a “guaranteed non-creepy approach”, it’s about addressing your sense of self-esteem and self-worth. It has far more to do with feeling like your interest is automatically unwelcome, rather than finding the exact right thing to say or way to act.

Another way folks will get tripped up is that not only will they try to solve the wrong problem, their solution is ineffective. The most common example of this involves your height, hair or other physical attributes, especially ones you can’t change. Many times, people end up wasting time, effort and (often) money in ways that only result in half-measures at best. If, for example, you have male-pattern baldness, you can spend a lot of time and cash trying to cure it, reverse it or hide it… or you could decide to get a close crop and focus on dating people who aren’t shallow assholes.

A plastic surgeon uses a pen to mark a patient's hairline in preparation for hair-replacement surgery
Hope you’re willing to pay for the privilege of a painful procedure that’s gonna leave you with doll hair…

It costs far less money, takes less time and gives you much better results, especially over the long-term.

When you want to get your love life unstuck, it’s important to focus your effort on what actually makes a difference. Where you’re going to meet people and which people you’re talking to, for example is important. People make a fuss over picking strangers up at bars or approaching women in the street when it’s much easier to connect with folks who share your interests and passions at a MeetUp. Being able to make someone laugh and have fun is vastly more important than being a “1% man” or having “the six sixes” or whatever.

The same is true about confidence and attitude. Most of the truly hard cases – the folks who struggle the most – tend to have shitty attitudes and absorbed all the wrong information, rather than the wrong face or build. This, in turn, just compounds things and makes them worse; your failures build frustration, frustration makes your attitude worse, you struggle even harder and get more frustrated and the cycle repeats.

In fact, many sticking points tend to be the result of having become invested in a lot of the wrong ideas about love, sex and dating. In many cases, it’s a classic example of “inventing a person to get upset at,” whether the supposed problem involves women who are overly privileged or picky or the mythical “Chad” who’s taking up 80% of the women. Other times, it’s a matter of inventing imagined reactions and responses based on your anxieties and responding to those, rather than reality. You’re not mind-reader, and yet it’s very easy to convince yourself that you know exactly what someone is thinking and why they clearly hate you… even when you haven’t said more than a handful of words to them.

Getting unstuck is all about chosing the solutions that will actually make a difference. Many times, this means adjusting what you’re doing or even changing your approach or goals. If dating apps have you down, it makes more sense to quit relying on apps and to focus on meeting people in person. You can spend time and energy trying to force blood from a turnip, or you can change your priorities and see significant differences within hours. Improve your in-person social skills and let Tinder or Hinge be the supplement to your dating life, not the focus.

But speaking of solving the right problem…

Don’t Just Remove the Brakes, Apply the Accelerator

When we talk about improving your dating and having more success with women, we’ll often focus on things that trip people up and ruin their chances. The most obvious example is being a classic Nice GuyTM; after all, women don’t appreciate men who try to be friends under false pretenses. However, what I often hear is “well, I’m not doing $_BAD_THING or $_OTHER_BAD_THING so clearly this is bullshit” or “Well I see people doing $_BAD_THING all the time and they get dates so that’s obviously not my problem.”

studio portrait on white of a smiling handsome young businessman holding up a credit card
“I’ve got my Official Woman Respecter card here, so CHECKMATE, Doc!”

Here’s the thing, though: not doing the negative thing isn’t a magic bullet. Not being The Worst doesn’t make you more desirable, it avoids making you less desirable.

What people often miss is the difference between a brake and an accelerator. Every change you make is either affecting either a brake or an accelerator. That is, you’re making changes that either hold you back, or propel you forward; the difference between not having a reason to say no and providing a reason to say “yes”. Behavior that turns people off or otherwise hinders your chances are brakes; they’re slowing you down or keeping you from moving forward entirely. Behaviors that improve your odds and make you a better date are the accelerator; they move you forward towards your goals.

The part people often forget is that dating success isn’t just about removing the brakes. Ceasing to do $_BAD_THING – or never doing it in the first place – isn’t the same as hitting the gas; it just means you’re no longer applying the brake. Taking your foot off the brake just removes the thing that impedes movement; it doesn’t move you forward unless you’re already going downhill… and that’s a problem in and of itself.

Now that doesn’t mean that you don’t need to avoid applying those brakes and only focus on the accelerator. If you’ve ever accidentally driven with the parking brake on, then you know how much it affects your car; you have to stomp on the gas to get even 1/10th of the speed you’re trying to reach. It slows you down, wastes gas and even damages the tires, brakes and engine. But at the same time, as long as we’re torturing this metaphor to death, you can’t JUST be all-gas-no-brakes; that’s how you go careening into trees and slamming into other cars.

There’s a reason why effective dating advice is all about the process and not magic bullet cures; even if you’ve got your foot on the gas and off the brake, you still have to drive the car. You can’t just shout “EVO-PSYCH TAKE THE WHEEL” and hope for the best; you need to be an active participant who’s actually directing the car where it needs to go.

Man standing in front of his car, with the hood up and smoke pouring from the engine.
And if you don’t change your oil every 3,000 miles you… wait, I think this got away from me somewhere.


This is why being told that doing X is harming your love life doesn’t mean that everyone NOT doing X should be knee-deep in sex; just ‘cuz you don’t have your foot on the brake doesn’t mean you’re driving. Or even have the engine on in the first place. Having success with women isn’t just about the absence of reasons to say “no”; it’s about giving them reasons to say “yes” to you as well.

If you’ve eliminated the “no’s” that are under your control and you’re still struggling, then the issue is about finding those “yes’” and actually moving the car where you need it to go.

Heal Your Wounds

This is the big one. I’ve joked about this with friends, I’ve recommended it to readers and I’ve brought it up in the comments on my site and I’ll say it here: sometimes you don’t need dating advice, sometimes what you need is therapy.

I’m not being dismissive or sarcastic here. A lot of the toughest nuts to crack and the hardest cases to solve are difficult because their problems have nothing to do with dating or attraction and everything to do with trauma and unhealed wounds. It doesn’t matter how snazzy you’re dressed or whether you have the gift of gab when you’re carrying around baggage and agony from things in your past.

Nate, Ted Lasso and Coach Beard watch the results of the Manchester City match against Richmond
And all of your defense mechanisms only hold the darkness off for so long…

As a general rule, you don’t need to be in perfect emotional shape in order to date, but you do need to be in good working order. And quite frankly, a lot of folks aren’t.

I can’t tell you how many people I’ve worked with whose dating struggles all stem from bulling or bad experiences in middle school or high-school, even decades later. The hurts they took at the time may seem small, petty, even pathetic in the scheme of things… but they’re still wounds, and untreated wounds at that. It doesn’t matter how stupid you think your trauma may be; if it’s hurting you and dragging you down, then it’s hurting you and dragging you down. And nothing will get better until you address the actual wound. You can cover it up, you can dismiss it or you can try to pretend it shouldn’t affect you, but that won’t help, any more than insisting that your leg shouldn’t be broken means you can run that marathon anyway.

Nor for that matter can I reasonably tally up the number of people I’ve worked with who were very clearly struggling with depression or anxiety disorders – often mixed with compensatory behaviors or forms of self-medication that only make things worse.

Nate, Ted Lasso and Coach Beard watch the results of the Manchester City match against Richmond
Turns out, constant jokes, distractions and refusing to take things seriously doesn’t magically make you a healthy person.

This is a hard truth for a lot of folks to face. It can be very difficult to admit that you need therapy or even may need medication. Even 2022, admitting that you need help, especially mental help, can make you feel like you’re admitting that you’re just a broken, weak person who couldn’t hack it. It’s a lot easier to – and I’m just going to pick an example completely at random that bares no resemblance to me – try to learn pick-up techniques rather than address a crippling fear of rejection that’s tied to decades of low self-esteem and an untreated mental condition.

Here’s the thing, though: you can’t just grind your way out of an anxiety disorder or chronic depression. You can’t flirt your way out of trauma. It’s the social equivalent of putting a bandage on a hemorrhage; it might hide the blood for a bit but it’s never going to actually stop the bleeding.

And to be clear: I speak from personal experience here. Yes, discovering that I’ve got ADHD with a heaping side of rejection-sensitive dysphoria made a difference. Getting the medication that lets me manage my ADHD made a huge difference in my life. But even my meds weren’t a magic cure for all that ailed me. I had years of wounds and negative experiences and beliefs that came from living with ADHD for as long as I had, wounds and experiences that also needed to be addressed and worked through. No amount of snappy clothes, cool hair cuts and clever lines will fix that. Only doing the work will.

Healing yourself is the single greatest gift you can give yourself. It’s not just taking your foot off the brake, it’s unhitching a trailer of bullshit and unloading all the unnecessary baggage that’s been weighing you down. And to be sure: getting help now can be difficult. Many therapists don’t have availability (or are traumatized themselves) or don’t take insurance. But there are other options out there. Captain Awkward has two excellent posts that detail how to get low-cost or even free mental health care in the United States and Canada. Sites like Mood Gym offer self-directed cognitive behavioral therapy exercises that can help with issues like intrusive thoughts and negative self-talk. Services like BetterHelp and TalkSpace can help make therapy more accessible, and even companies like Roman are investing in mental health telemedicine services.

These may not be a replacement for sessions with a therapist or counselor, they go a long way towards helping you heal. And that healing is important. Think of how much you could do if you could work through your trauma. Think of how much faster and further you could go without your pain holding you down. Imagine how much you could accomplish if you let your past hurts go and embraced your best, healthiest self.

I know I’ve said before that we are often our own worst enemy. But often, we are our own enemies because we cling too tightly to our past and our pain because it’s what we know. We’ve held onto it for so long that it’s hard to imagine life without it or, worse, come to believe we deserve it. But the time has come to let go. It’s well past time to stop embracing the hurt like a lover and set yourself free.

It’s time to let go of your earthly tethers and soar like you were always supposed to.