TheĀ Dating Engineer Blog

Helping you optimize your love life.

6 Keys To A Successful Dating Life

Jan 21, 2024

“We’re happy, free, confused, and lonely at the same time.”

Never thought I'd start an article with Taylor Swift lyrics. I understand if you want to leave immediately.

I recently read them and thought they were relevant for this article. In my opinion, T-Swift's popularity at this time is indicative of this fact: our society is filled with TERRIBLE dating and relationship advice, for both men and women. On this site, I focus on men.

Can’t get a girlfriend? You gotta be yourself, be confident, and put yourself out there.

Just broke up? The best way to get over someone is to get under someone.

Feeling lonely? Just be patient. Your soulmate is out there.

Dating and relationships are viewed as a solution to so many problems. In reality, people use dating as a way to escape their incomplete inner world.

For men in particular, dating is a fantastic vehicle for growth. However, there are areas of your life that you should work on before you jump into the dating pool. Of course, the areas are different for someone who wants to date casually vs someone who wants a serious relationship, but the list I created below applies to any guy, no matter what they’re looking for.

Each item on the list could be an article on its own, but today I’m going to give you the essentials. We’ll deep dive later.

Are You Okay With Being Alone?

I would bet a lot of money you read that and said you’re okay with being alone. And I think you probably are if we take that in the literal sense. You’re okay with being by yourself. You probably spend plenty of time by yourself and maybe prefer it that way. You might be used to not being in a relationship, even if you would prefer to have one.

But do you actually, deep down, feel lonely and HATE IT?

It’s totally normal. Nobody likes feeling lonely, especially if we are surrounded by people who are in happy relationships.

However, feeling lonely can lead to a lot of unhealthy decisions when it comes to dating.

That can show up in the form of overlooking red flags, lowering your standards, spiraling when things don’t work out with a girl, hurting women, and many other behaviors you should avoid.

Before you start dating, you should be at peace with yourself. You should not feel lonely, even if you are alone. I promise it’s achievable. 

"Until you get comfortable with being alone, you'll never know if you're choosing someone out of love or loneliness."

-Mandy Hale

How do you achieve it?

For starters, dedicate a certain amount of time when you accept that you are going to be totally alone, romantically. 6+ months is what I recommend. You are not going to have any female companionship. You will be focusing only on yourself and your friendships. 

Most guys never do that.

Even if they aren’t actively trying to find a girl to date, they have eternal hope that they will get lucky and meet a girl while out at a bar or at a friend's party. Or they are frequently thinking about a girl, real or hypothetical. Or they have accepted being alone, but not by choice.

If done properly, this will be one of the most transformative times of your life. During this time, focus on the other items on this list. You can also prepare for when you will re-enter the dating world. Educating yourself on what healthy dating and relationships look like is never a bad thing.

Over time, you will find yourself becoming truly happy due to not having the anxiety in your life that normally comes with focusing on women. You will be fine with not dating and you will be truly happy. 

That’s when the real results come.

Do You Have A Solid Social Circle?

You know what helps prevent feeling lonely? Having really good friends who you can rely on.

A recent study from Applied Psychology found that men’s social network is very closely linked to their mental health. The fewer friends men have, the higher their rates of depressive symptoms.

Numbers aren’t everything. It’s possible to have friends and still feel lonely. That’s why it’s important to make sure you surround yourself with people who genuinely care about you and don’t add any negativity to your life.

How many friends do you have who are great overall but… 

  • they suck when they drink or
  • they’re super flakey and unreliable or
  • they don’t put as much effort into the friendship as you or
  • they have any other traits that negatively impact you?

You should do your best to cut people like that out of your life entirely. I know it’s hard to do, but it’s true what they say: you are the total of the people who you spend the most time with.

The more negativity you remove from your life, the more room there is for positivity.

A few really good friends is all you need. More does not equal better, although the more GOOD friends you have, the better.

However, if you don’t have many friends to begin with, you need to put more effort into making friends. I’ll write about all of this in more detail eventually, but I think people don’t appreciate how much effort is needed to create a solid friendship. It takes consistent effort over a period of time, just like any other type of relationship.

It’s also hard to find people who understand and reciprocate that energy, but once you do, you have lifelong friends who can help you get through anything. Don’t waste your energy on people who don’t reciprocate your efforts, and you’ll have plenty of energy to find people who do.

Are You Working Towards A Career You Love?

This is another subject we’ll be visiting someday in a lot of depth. Your career is a huge part of your life, and you should spend it doing something you are proud of and find fulfilling.

Being excited for Mondays will not only dramatically improve your life, men who have drive and ambition are very attractive to women. And no, not just for financial reasons.

Of course everyone would prefer to have a job they love. The question is how to get there.

That’s why I titled this section “working towards a career you love” instead of “have a career you love.”

Finding a career you love is hard, and getting there is even harder. Most guys, especially in their 20s, are still trying to figure out what they want. That’s totally fine. 

As long as you are making decisions that you think are in the right direction of where you want to go, that’s all you need to do. It’s okay to not know exactly what you want your final destination to look like. Explore new things, pursue what you’re passionate about, and do your best at everything you do. Eventually you’ll get to where you want to go.

A lot of guys, instead of being deliberate with their choices, simply drift through life. Drifting is directionless. You want to be moving forward and up.

If you are confident in the direction your career is headed, women will be too, and both of those factors combined will make you happier and hard to resist from a woman’s perspective.

Are You Maximizing Your Looks?

Do looks matter? Of course they do.

Studies show how much easier life is for good-looking people, and that applies to the dating world as well.
However, I want you to internalize these two points:

  1. Looks are not everything.
  2. What you do with the looks you have is more important than the looks themselves.

I can’t tell you how many good-looking guys I’ve seen who have a hard time with dating, because they aren’t maximizing their looks.

Most guys do not:

  1. Wear clothes that fit well
  2. Workout and diet consistently enough to be in very good shape
  3. Style their hair
  4. Update their wardrobe
  5. Use skin care products

This list could be extremely long, but you get the idea. These are all within your control, and women notice every single one. Even if you aren’t the naturally best-looking guy, what you do with the looks you have says a lot to women about how confident, self-aware, and socially calibrated you are.

No matter what your height is or how "ugly" you are, any guy can do reasonably well by exhibiting secure and authentic behavior. Insecurity is a massive turnoff to (high-quality) women, no matter how hot a guy is.

You don’t have to be Henry Cavill, but you should have the basics of physical self-care down before you enter the dating world.

Do You Have High Self-Esteem?

Let me ask you a question: what is the difference between confidence and self-esteem?

Seriously, take a second to think about it.

Most people use these words interchangeably. Understanding the difference is extremely important. In a nutshell, confidence is your belief in yourself. Self-esteem is truly valuing who you are.

You know the cliche lady's man from movies/tv who is extremely confident and hooks up with a lot of women, but never seems to have lasting relationships? Our society tends to venerate men like this, but deep down, a lot of these guys have low self-esteem. 

Hank Moody from Californication is a fascinating character and prime example. He is confident and sleeps with plenty of women, but he can never sustain his relationships and hates himself because of it, leading to self-sabotaging and further failed relationships. It’s a sad cycle.

People with low self-esteem tend to seek external validation to make themselves feel good. Whether that’s sleeping with a lot of women, being hyper successful in their career, or finding a troubled girl to “save,” these types of men are usually (not always) incapable of having healthy, truly fulfilling relationships. They are lacking something important inside, and they attempt to fill that void with external sources. The void can only be filled from within.

This is a deep topic that traces back into childhood for most people. For now, your takeaway should be this:

People with low self-esteem make poor decisions, and they attract other low-self esteem people who they hurt and get hurt by.

Improving your self-esteem is a long journey, but following the advice in the previous sections is a great start. It also needs to involve a lot of deep, inner work and possibly therapy. However, it is the single most powerful thing you can work on to improve your life. 

Being free of insecurities and losing the inhibitions that prevent you from being your authentic self is rewarding like nothing else.

Are You Content With Your Life?

Ultimately, you need to be content with your life before you start dating. If you are using dating (subconsciously or not) as a way to make up for something missing in your life, you are going to have a bad time in the long run.

That’s why I started this article talking about society’s terrible advice. Society pushes people to act now, move fast, and don’t think too much about what you’re doing.

Going on dating adventures, sleeping with lots of girls, and finding your soulmate all sounds amazing, but if you’re not emotionally ready for it, none of it is going to measure up to your imagination. When you don't have the results you wanted, you will feel terrible and probably resort to unhealthy behaviors.

So before you download Tinder or swipe on another profile, ask yourself this: are you truly content with all areas of your life besides dating? If not, focusing on those areas first will only improve your dating experience.

I have nothing to gain, and much more to lose by telling you to put the brakes on when it comes to dating, but I want you to have a successful and happy dating life. That won’t be possible if you’re not ready, and being ready means being truly content with your current life first.

It might take some time, but it’s worth slowing down and investing in yourself first. Our society likes to rush everything, but there is no rush. There will always be plenty of beautiful women out there who you can have an amazing relationship with. Plus, as a man, you thankfully aren’t as limited as far as your biological clock goes.

I’m also not going anywhere. When you’re ready to date, I’ll be here to show you the way to the dating life of your dreams. In the meantime, I have plenty of non-dating-related advice to give as well.

To make sure you’re always able to find me, enter your email address below. You’ll get lots of free content that you’ll be able to go back and read whenever you’re ready.

Now go be your best self!

-Coley

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