9 Ways You’re Making Dating More Complicated and Difficult (and How to Overcome Them)

Most people get in their own way more than anything or anyone else.

For most of us, this greatest barricade blocking our happiness and success (in relationships and beyond) is ourselves. We fail because we’re stuck in our heads, self-sabotaging, or acting in a way that we don’t even realize is deeply problematic.

The greatest enemy for most of us is staring right back at us in the mirror – blocking our every move we make to make our lives better, easier, and happier.

But you don’t need to be trapped in a loop of negativity forever. You can break free, become more self-aware, and start to live your life on your terms. To date on your terms.

Dating is fairly simple, but people make it complicated. People, with their issues, bad habits, and unprocessed traumas, make dating very, very difficult.

That being said, you can simplify your dating life if you break free from these 9 problematic habits.

1. You Don’t Know What You Really Want

If you’re dating without knowing what you want out of a relationship, you’re being disrespectful to the person you’re spending time with.

Honestly, no matter how I try to spin it – the hard truth is that dating without clear intentions on any level is a waste of both you and the person you’re dating’s time.

If you don’t know what you want, this doesn’t expel you from dating entirely, but it does expel you from the possibility of telling someone that you want a committed relationship with them.

Or a casual fling.

Or anything other than the truth, for that matter.

A good rule for life is to tell the truth, and most people follow this until they start dating. Once they start dating, they want good feelings. They don’t want to hurt the person they’re seeing. They don’t want to lose the person who makes them feel good.

You can’t act or think like this. You need to figure out what you really want to pursue romantically – not just for your sake, but for the sake of anyone you’re dating.

You do this by organizing your thoughts – writing them out, speaking them out loud, and spending time by yourself.

2. You’re Still Hung Up On Your Ex

What a tragedy – to be living in the past trying to recreate a relationship that is dead – a relationship that you don’t have anymore.

When people are stuck on their ex, it’s usually because they “over idealize” them.

This manifests itself in a few different ways.

Sometimes, they try to chase their ex around, whether or not the ex has moved on. It doesn’t matter – all the person wants is their ex back. They are living in the past and they want what they had.

That’s all.

Or, they try to recreate what they had with their ex with someone new – this is equally problematic because they are unconsciously objectifying the new person that they are with. They don’t see them as an individual but as a person whom they can use to recreate feelings of the past that no longer exist.

When you realize that you recreate the past or get your ex back, you’re in for a rude awakening.

Move on – no matter what.

3. You Don’t Know How to Communicate

You probably know words and sentences and probably even some big words, but do you know communicate your complex emotions?

Can you explain to someone what you want, why you do things that are bad, and can you apologize?

In relationships, you need to communicate, and not the way that you communicate with the person making your coffee at Starbucks or the person who cuts your hair.

In romantic relationships, trust and communication are foundational. You can’t really hope to date anyone for a long time until you can communicate at a fairly high level. You need to know to listen, learn from behaviors, and express yourself well.

If you can’t do this, dating will always be a challenge and you’ll always feel like you and the person you’re with are not on the same page. Miscommunication will be common in your life until you view communication as a skill that you need to build.

Until you study communication (here’s a great book to help you get started), you will always inadvertently make dating more complicated than necessary.

4. You’re Too Picky

It’s good to have standards.

You don’t like it if someone doesn’t have a job, has bad hygiene, or something like that? Good. I don’t it either. I applaud you for having the self-esteem to know what you want.

But there comes a time when you’re not really “having standards”, you’re just being picky. You’re being obnoxious. You’re making your dating life harder because you won’t date someone because of a pimple, a laugh, or something small like that.

In Seinfeld, there’s an episode where George is dating a girl and he decides he doesn’t like her nose. Then, she gets a nose job, it goes wrong, and finally, it gets fixed.

But in the process of the whole nose thing, George and her break up. George was crazy about this girl – except for her nose. He lost her because he couldn’t see past a flaw.

George ends up alone, and the girl ends up dating Kramer.

Remember, this is a comedy show. It’s supposed to be ridiculous.

And yet, it’s not ridiculous at all. Peope always have relationships like this in real life. We try and change our partners, fix them, and make them better.

Don’t be like that. Learn to accept people you claim to care about.

If you like someone, you should learn to see past their flaws and love them for who they are. If you can’t do this, don’t date them, and probably don’t date anyone.

5. You Won’t Commit

I used to have the strangest problem in my relationships.

I couldn’t make it past the 6-month mark. Every time a relationship got near that 6-month mark, something would happen.

At first, I thought it was a series of coincidences. I thought that it was an accident. I figured it couldn’t have been my fault of all things.

I was wrong.

In general, if you are running into the same problems in relationships over and over again, you are the problem. You are the only common denominator in all of your romantic relationships.

This means that if you want to break a cycle, you need to change. You need to grow.

For a lot of young men, that means that you need to break free from your fear commitment and just take a chance. Take a risk.

Open yourself up to the possibility of a relationship failing and you being hurt – even if it’s scary. Even if it feels nerve-wracking.

If you love someone, commit to them and do your best to make it work. Have fights – solve them. Have good days – enjoy them. Have bad days – endure them. This is love, not whatever you’ve been told in Hallmark movies and by self-help influencers. Love is about enduring.

In the best-case scenario, you’ll be happy. Worst case, you’ll end up with some great lessons to make your future relationships better.

It’s a win-win, but it’s a scary chance to take.

6. You Self-Sabotage

Self-sabotage is tragic not only because it’s completely avoidable, but because it leads to devastating consequences.

You don’t just have bad days from self-sabotage, you lose relationships, people, and opportunities. Self-sabotaging behavior can ruin your life, and you must do everything you can to avoid it and stop doing it.

But of course, it isn’t that simple.

If you’re someone who makes a habit out of being your own worst enemy, you need to identify the triggers and incidents that lead you to sabotage yourself.

Don’t get upset that you self-sabotage (this usually leads to more self-sabotage) – this only makes it worse. Instead, try to figure out why you self-sabotage. Identify the root cause of the issue.

Also, remember that self-sabotage takes many forms. It’s not just self-destructive behavior, it’s also perfectionism, self-medication for comfort, and even procrastination.

So, if you struggle with self-sabotaging, and you’re procrastinating trying to do something about it, you’re self-sabotaging yourself by not working to improve your self-sabotaging issue. You’re hitting yourself with a double whammy, and it’s killing your chances of having good relationships.

Because people are so complicated, dating is hard enough as it is. Don’t make it harder by being your own worst enemy.

7. You’re Too Insecure

Insecurity is a form of self-sabotage, but it’s so deeply rooted in people’s psyches that it’s really its own issue.

In many cases, insecurity leads to self-sabotage.

The problem with insecurity is that it creates a scarcity mindset in dating. It makes your relationship seem like the make-or-break thing for your happiness. You start to operate with an “all-or-nothing” mindset.

If you’re insecure, you’re happy when the relationship is going well and miserable when it’s struggling. You also might think that your partner is the key to your happiness – that your relationship is the key to your peace.

You’re idealizing someone or something because you are not secure with yourself.

At the same time, your insecurity will lead you to do crazy things “in the name of love”.

You won’t trust your partner. You won’t be yourself around them. You will to do whatever you need to do to make the relationship work, and if it’s not working, you’ll resort to self-protection. You just want it to be okay because your insecure ego can’t handle the idea that it won’t be.

Sound like you? Do you feel personally attacked?

Good. That means you need to work on yourself. You’re better than that.

No relationship can make you complete. Nothing will solve your insecurity but yourself.

Ironically, once you work on yourself and become less insecure, you will struggle less with relationships. You will feel more complete and thus will start having the kinds of relationships you truly want.

8. You Won’t Put Yourself Out There (Enough)

This is a big one that a lot of men today struggle with.

Men today are approaching women less than ever.


Well, there are a few reasons, most of which are completely unfounded.

Men are approaching women less because they don’t want to “seem creepy”, they don’t to face the negative feelings of rejection, and because they’re distracted by other sources of cheap dopamine.

They’re distracted by porn, social media, Netflix, and more. Why risk going out and asking a girl out when you can just order a pizza, watch a movie, scroll Twitter, and put on your favorite porno again?

The dopamine rush from not pursuing women to many men is more worth it than the risk of possibly failing at pursuing them in reality.

This is a problem.

If you want to have relationships in real life, you need to pursue them. You need to embrace the risk of failure and rejection because it’s probably going to happen to you. Compatibility is a real thing. Rejection is a real thing.

But it’s really not that big of a deal. Rejection is not always an assault on your character. Sometimes, a relationship is just not the right fit.

Develop an abundance mindset and have the best relationships of your life.

There are plenty of fish in the sea – but you can’t have any fish if you don’t actually go fishing.

Oh, and as we’re about to talk about. You need to get good at fishing too.

9. You’re Just Unattractive

Too harsh?

Let’s talk about this really quickly, because it’s an interesting problem. If you want to have good relationships, you need to be desirable. You need to become attractive.

How do you become attractive as a man?

Well – you do a few things that are pretty simple and pretty easy to adopt, but for some reason very difficult for a lot of men today.

You need to be fit, you need to be confident, you need to probably have a decent career (or be working on one), and you need to have some charisma – some “game”. You need to know how to flirt, make a girl feel desired by you, and how to show her that you’re interested.

But let’s focus on those first few points because they’re really important. You, as a man, need to transform yourself into someone who is worth having relationships with. Someone who is attractive to women.

When you become someone who is attractive to women, you will start to become someone who women not only want to be with but someone who they will seek out. This small shift will make your dating life so much easier.

And, likewise, if you are not doing everything you can to be the best that you can be, you will repel women like the plague.

It really comes down to discipline.

Work on yourself, develop some dating skills, and watch the power of discipline change your dating life change forever.


I said this in the introduction and I’ll reiterate it here because it’s imperative that you understand it.

Dating is simple, people make it complicated.

You can have great relationships, but there are a few things you need to do first.

You need to become a man who doesn’t get in his own way. A man who leads. A man who’s charismatic. A man who doesn’t fear committment. A man who knows what he wants, but isn’t too picky.

You need to do the work to become the man you’ve always wanted to be.

I can help.

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