How To Stop Hating
The Dating

Some men seem to have natural, effortless charm with women.

And I bet if you ask them what they’re thinking about when they’re meeting new women or on a date, they’ll say something like…

“I’m just looking to have a good time.” or “I’m trying to have some fun.”

Their #1 priority is to enjoy themselves.

That mentality enables them to have fun experiences and coincidentally…see great results.

But it’s usually difficult for them to explain HOW they do that. They tell you, “don’t overthink it,” or “just be yourself”.

Those things aren’t easy to do! Having “fun” with a brand new romantic interest doesn’t come naturally to most of us. In fact, you may see the dating process as anything BUT fun. To you, it could be a grueling, anxiety-ridden experience filled with awkwardness and rejection.

So how do you change that? How do you learn to have more fun and therefore, see more romantic success?

The Emotional Rollercoaster Of External Validation

I’m sure you already know that some of the qualities women find most attractive are a sense of humor and a positive attitude.

So maybe you go into new romantic situations thinking…

  • “How do I make her like me?”
  • “What will she find funny?”
  • “How can I make sure I don’t say anything that upsets her or turns her off?”

It’s awesome to want a woman to enjoy herself — but focusing ONLY on what SHE likes puts a massive amount of pressure on you. You’re stuck constantly trying to decipher what she thinks is fun or funny.

This places you in an approval-seeking mindset where you feel like it’s your sole responsibility to make everything go smoothly and ensure she likes her time with you.

That’s damn near impossible since you barely know her!

If these external factors are your measure of success, you’re at the mercy of circumstances out of your control. Luck, incompatibility, and her emotional availability will dictate your happiness within those social experiences.

I believe this mindset is the root of why many men can’t enjoy the dating process.

I used to see this in myself and with other guys that were obsessed with “picking up women”. They’d go out and experience what I called the Emotional Rollercoaster.

No matter how interesting a night they had, their entire feeling about it was determined by whether or not the women found them funny and desirable.

One night they’d talk to a few girls, get some numbers, and be on top of the world. The next, they’d struggle to connect and absolutely hate the whole experience. They would be emotionally wrecked and regret ever going out in the first place.

Dating isn’t supposed to be like this. And it’s NOT sustainable.

The Trap Of Entertaining Everyone Else

No one looks forward to going out and getting rejected. Or spending three hours on a date that never turns into something more. So it’s normal to try to control your romantic experiences and minimize risk.

But as I said, always thinking about pleasing the other person works against you. Because that means you’re not focusing on how you can enjoy yourself more.

Instead, you only talk about what you think they want to talk about. You ask the questions you think they want to answer.

You avoid your weird sense of humor that they may not appreciate. You don’t talk about your quirky hobbies that get you giddy and excited.

While you may think playing it safe and focusing on entertaining women is a good strategy, it really just dulls the charismatic and passionate sides of your personality. Your constant micromanaging and holding yourself back doesn’t come off as “fun”.

So instead, girls are less engaged and attracted to you. Because again, they’re attracted to men who like to enjoy themselves.

Now you’re get worse results, hating those interactions, and loathing the next time you have to put yourself out there. You’re also less likely to have fun during future experiences — creating a self-defeating cycle.

Shift Your Perspective Inward

Starting to have fun with dating begins by shifting your perspective inward. You need to let go of trying to figure out how SHE can have fun and instead prioritize…

“How can I enjoy myself as much as possible?”

Then hold yourself accountable to act in those ways and form new habits.

This can be difficult because you may worry: “What if she doesn’t think I’m funny? What if she thinks I’m boring?”

That doesn’t really matter in the bigger picture. Because this is the most important thing you need to understand…

Women don’t have to have the same exact style of humor as you or love the same things as you do. What matters more is whether or not they can feel that you’re truly enjoying yourself. That will almost always trump everything else.

People have the most fun when you’re ALSO having fun.

Because when you do, you’re conveying a much more important, powerful message: “I like who I am and I’m not afraid to express my authentic self.”

That is the essence of self-esteem and confidence — and it’s what people are deeply attracted to.

It’s about being a man who knows who he is and is unashamed about it. He’s not seeking other people’s approval. He would rather find someone who can appreciate his real personality than pretend to be someone else.

That’s why if you go to clubs there’s often some guy being a goof, flailing around dancing his ass off. Yet you still see women gravitate towards him more than other guys chilling around trying to look “cool”.

Do you think those women are attracted to his awkward, embarrassing moves?

Definitely not. But they ARE attracted to the fact that he gives no fucks about what people think and can truly let loose. That outweighs everything else.

There’s a sense of trust there that regardless of your differences, you can still manage to have a good time together.

Figure Out Your Own Ways To Have Fun

Enjoying yourself is not only about making jokes and laughing. Some people are not as playful or comedic as others, and that’s fine.

It’s about acting in ways that are congruent with your values, interests, and opinions. And therefore having connections or conversations that are engaging, fulfilling, and amusing to you. It’s also about not doing things that make you miserable or bored.

Most of all, it’s about taking the seriousness out of the situation. This is just an interaction with one random person. You’re not going to war. You’re not giving a State of the Union address.

For example, I have a client who hadn’t been having fun nor success on his dates. He’s got a colorful personality and dark sense of humor.

Every single date he hid that side of himself. He thought it would be too off-putting. Finally, on a date a girl asked him about his guilty pleasures. In that moment, he stopped worrying about what she’d think and just answered:

“Sometimes I get really high and watch Powerpuff Girls reruns on YouTube.” (a cartoon with some adult humor).

The girl couldn’t stop laughing and her vibe changed immediately. She started opening up about her more eccentric side and they developed real chemistry. They ended up spending the night together.

Now of course, you don’t need to talk about drug-induced cartoon binges. But you do have to think about what’s funny, true, or engaging to you.

Sometimes, it’s makes it easier to think about the social experiences in which you naturally have the most fun. That could be with a certain friend or family member. Think about how you interact with them.

What subjects could you talk about forever? How do you express your opinions with them? What kind of humor do you use? How loud or passionate do you get? Do you like to get sarcastic and absurd?

However you act when you’re having a great time, that’s how you should practice acting with women you want to date.

Build New Habits For Self-Enjoyment

So the next few times you’re trying to meet or date new women, make having fun your only goal. Trust that if you do that, the results will come.

Here are some ideas that have worked for guys I know:

  • Choose date ideas or locations that you already enjoy. Pick environments that you feel comfortable or knowledgeable in. If you’re outdoorsy, take her on a hike. If you like live music, see a cheap local band. If you’re into art, check out a new museum exhibit. You’ll play to your strengths and have a lot more to talk about.
  • Think about a funny story you’ve told before and tell it to your date. Share something silly that happened to you recently. Repeat a joke a friend told you that made you laugh your ass off.
  • Before you go out for the night, listen to your favorite music or standup in the car. Turn it up. Sing loud and act like a fool. Get pumped up and let that carry over to your date.
  • When messaging with online dating, skim a woman’s profile for singular words or ideas that resonate with you. Then say some silly, absurd, or random shit about it. Learn something from Eric André and Hannibal Buress. You don’t have to be extreme or vulgar like them. Instead, understand how they just say ridiculous things to amuse themselves. Again, it’s better to have some fun than be bland.
  • Get onto subjects that you’re passionate and knowledgeable on dates. Don’t always follow the topics other people want to discuss. We instantly become engaged when someone talks to us about things we find meaningful.
  • If bars aren’t your thing, find hobbies or activities that you’ll enjoy, be challenged by, or learn something new from. Then coincidentally meet like-minded women through them rather than always cold approaching.
  • If you’re on a date and she’s religiously checking her phone, playfully call it out. Say something like, “Didn’t your mom tell you no phones at the dinner table?” Why endure an awkward, disengaged date? Don’t let people test your values or your experience and make you miserable, challenge them back. 
  • Turn your approaches into a game. Take a random absurd word and bet a friend on who will be the first person to use it in a conversation. Or who can be the first person to introduce themselves to 3 people and shake their hands.
  • When you’re at a place with music, focus on feeling the beat. Ignore everything else around you and just dance like you would at home. Eventually, you’ll notice people gravitate towards your positive energy and they’ll be much more open to dancing with you.

Overall, the more seriously you take the dating experience, the worse time you’re gonna have.

So I ask you… 

How often do you laugh on dates or when you meet someone new? Are you having fun during those experiences?

Your answers to those questions will dictate your enjoyment and success.