How Important Is It to Have Fun When Meeting Women?

A lot of guys want to be the cool, suave guy. They want to be the stoic James Bond type who smoothly and aloofly maneuvers his way through an interaction and ends up with a girl in his bed.

But a lot of guys neglect the fact that even Bond had to go through a whole lot of BS to get to that point. And even though he’s suave, Bond is always having a great time when he’s seducing a woman.

have fun meeting women

The fact is: seduction should be fun. And the fact is: most people won’t be like James Bond. You have to have a very particular kind of personality to be that way. However, a lot of guys can learn how to have fun and greatly boost their results with women.

So let’s look at the importance of having fun in your interactions, and how it affects your success and satisfaction.

You Win Some, You Lose a Lot More

I was out recently with a good friend/wingman. I was feeling a little frustrated because we had just spent 45 minutes with two cute girls who were really into us, but who then ran off randomly after admitting that they both had boyfriends. I was feeling tired, and I wasn’t quite prepared to be hurled back to ground zero so abruptly. And I was definitely a little down on the prospect of having to reopen and rebuild rapport with new girls.

But as soon as I had that thought, two even cuter girls popped into the scene. And when I saw them, I immediately perked up and knew that I couldn’t let the miasma of my disappointment from the last interaction taint this new one. It would’ve been unfair to the new girls and it would’ve been unfair to us as men.

With this new reinvigoration we began talking to this new pair of girls, and I was hitting it off with one of them even more than what I had been experiencing with the first girl. This girl was really attractive; she was also silly, funny, and really confident. The four of us then embarked on an amazing adventure.

Yet, even though I was leading, escalating, and really playing the interaction quite perfectly, I always had one thought in the back of my mind: “I need to make sure that I have a good time, because I need to be ready to let go of this interaction at any point.”

Things were continuing toward the crest. She and I were holding hands, exchanged a light kiss, and she adamantly voiced her excitement for the after party at my place that I vaguely referenced. However, my wingman wasn’t faring so well. It wasn’t really a lack of game (he’s very good looking and sociable), but more a matter of circumstance. Little did we know that his girl was already hooking up with a guy who was on his way to the bar we were at.

Upon this man’s arrival (with a few of his friends), we were at an impasse. He wanted to take my friend’s girl and his crew back to his place (which was far away and in a very unfamiliar location). My girl wanted to come back with me. But, she couldn’t risk looking like a whore, so she attempted to part ways with me with a nice friendly handshake. I was more offended by the gesture than I had originally thought, and I felt myself go into slight auto-rejection.

But then I remembered my thoughts from earlier and parted ways with her as calmly as I could, knowing that I would never see her again.

At the end of the night, my friend apologized for the way things had turned out. “Don’t worry about it!” I told him. “I had a phenomenal time tonight. I learned a lot about myself and I had a lot of fun.”

And I was being completely truthful. I did have a lot of fun. And I realized that making sure you’re enjoying an interaction is a key to success in game. It’s not the only factor obviously, but it is an important one.

However, making sure you have fun is the most important aspect to staying determined and driven to move past the many failures you’ll experience along this wonderful journey.

Why is Having Fun So Important?

So we’ve already established that having fun is the most important aspect to keeping up your perseverance and energy when trying to improve your success with women. Now the question is: why?

In order to answer this question, let’s look at two different scenarios:

Scenario #1: Imagine a sport/activity you absolutely hate doing. For me, that would be long distance running. I’ve always loved sprinting, but as soon as you push the distance past about half a mile or so, I absolutely despise it. But when I played sports in high school, the coaches would always force us to run several miles twice a week in order to improve our endurance and our stamina.

And I dreaded it every week. I didn’t care about improving my times. I didn’t care about upping my resilience – I just wanted to go home. And I seriously considered quitting every sport that I was involved in that had long distance running involved in it. I stuck with most of them, in the end, but every time was a constant battle with my own will as to whether or not I should even go to practice on distance days…until I had a mental shift.

Scenario #2: Imagine a sport/activity you absolutely love doing. For me that’s dancing. For many days and nights of many years of my life to this day I have happily put in hours upon hours of studio time, performance time, practice time, and just mess around time to improve my dancing. It can be absolutely grueling sometimes, but it’s always enjoyable to push through the pain and know that you’re engaged in an activity that you’re passionate about.

have fun meeting women

And the funny thing is, whenever I’m out at bars or clubs or in public and a song comes on that I want to dance to, people think that I’m trying to put on a show for them or impress them. But dancing to that song is something I would do anyway –regardless of whether I was in public, in a studio, with a couple of friends in the wilderness, or alone in my bathroom. And because there’s that inherently fun aspect to it, I’m always determined to get better – and sometimes hit a quantum leap before I even really notice that I’ve done so.

Back to Scenario #1: One day before one of our sports practices, Omar, one of the fastest guys on the team, approached me.

Him: Yo Colt, someone told me that you suck at distance [running].

Me: Hah, I don’t like doing it, but I wouldn’t say I suck.

Him: Oh yeah? Care to make a wager on it?

Me: Go on.

Him: If you can finish within twenty seconds of me on a three mile run, I’ll buy you Chipotle and carry your stuff there. But if I win, you buy me a burrito and you have to kiss my sweaty feet.

[I was set off by this challenge – both offended and motivated at the same time]

Me: You’re on.

And for the rest of the afternoon, he and I were just trash-talking each other. It was the best form of friendly competition (and we were getting pretty creative with our jokes, if I do say so).

And when the run started, I didn’t have the usual thoughts of boredom and exhaustion that normally frequented my mind. All I could think about was winning that bet and not having to kiss those damn feet. I was also thinking about what witty lines I could pull out when I seized my victory.

That day, I ended up winning the bet by a hair. But what was more important was the mental shift that happened to me. Every day after our infamous race, I started trash-talking and joking around with Omar and with a bunch of other people on the team.

And every day I would get closer and closer to actually looking forward to distance running. I stopped thinking about the pain, exhaustion, and tedium, and started thinking about how I could push the people around me and make it fun for myself and everyone else.

And that’s the shift that all successful men make with women. They stop trying to brute force their way through interactions and try to make it fun for themselves. The fact is: most of your interactions with women aren’t going to go anywhere. So when all is said and done, if you didn’t enjoy the time you spent during the interaction, then my friend, you just wasted that time.

You should be learning from every interaction, and you should be learning to enjoy every interaction with girls.

On that night I was in the mountains, I shared that thought with my friend. I’ve been at this longer than he has, so I think he’s still more invested in particular outcomes than I am, rather than looking at the bigger picture like in the stock market.

I believe that having fun and always being ready to let go of an interaction when you have to prevents you from becoming too invested in her and keeps you on your toes to make sure that you keep her investing.

The Two Different Kinds of Achievers

One of the best nonfiction books that I’ve read recently is What Makes Your Brain Happy and Why You Should Do the Opposite by David DiSalvo. It’s essentially a book on how our brains trick us into making snap judgments and poor decisions and outlines how to go about reversing the negative tendencies that are deeply wired into our minds.

A great section of this book is a discussion of the two different kinds of achievers. Essentially, DiSalvo breaks down all people into two categories of motivation and achievement:

  1. People who are driven by metrics. These are people who want to overachieve, and have their likelihood of success boosted by words like “prize, esteem, success.” And interestingly enough, when you give them a task and say that it’s going to be “fun” their performance actually goes down.

  2. People who are driven by fun/creativity. These are people who want to enjoy what they’re doing in order to bring about a high-quality result. Their likelihood of success is boosted by words like “fun, collaboration, freedom.” Similarly to the first group, if you prime them with metrics-based stimuli like “achievement” their performance will go down.

In terms of your approach to life and game, it’s of the utmost importance to understand what kind of achiever you are. However, with women specifically, regardless of which category you find yourself in, you need to learn to adopt characteristics from the other category.

  1. For people who are driven by metrics. I have a few good friends who are very analytical people. They like every decision to be logically broken down and are only satisfied by results. When I was first getting started (and hell, even now) it was hard to go out and approach girls with these types of guys because they didn’t understand the concept of racking up rejections.

At times I would break it down in a very numbers-based way to show them that X number of rejections will eventually yield Y number of phone numbers and Z number of lays/dates depending on your skill level. And although this method worked, they would still be entirely too in their own head to be socially effective.

So instead, I started doing exercises with them to help them have fun and let go. We would do funny dances, yell ridiculous things, and otherwise loosen ourselves up when approaching girls. And these exercise really helped these guys relax and get more enjoyment out of their night. They would still go home and analyze, but they could at least live in the moment somewhat and enjoy the process.

have fun meeting women

  1. For people who are driven by fun. Some guys learn a few game techniques, and then go out, throw some out here and there, have a great time – maybe build up some attraction – and then go home empty-handed. They talk about the girl who was “so into them” and then kind of leave it at that. I would definitely put myself into more of this category.

Guys who like to have fun need to make a conscious effort to analyze their interactions when they go home. Nowadays, even though I do go out and have a great time, if I don’t end up taking a girl home, I will spend a non-trivial amount of time breaking down the interaction. Sometimes I’ll go over it with my wingman if I have one (an immensely useful exercise).

I’ll think about what I said, what I did, what she said and did, where the highlights of the interaction were, where I missed escalation windows, where the interaction began to taper off, and any other important facets of the exchange. Then I wrap up by giving myself lessons and takeaways to help me avoid that mistake or to compel me to try something new with the next girl. This exercise helps fun driven guys still go out and have a great time, but hold themselves accountable to follow a process and keep improving.

How to Have Fun Meeting Women

  • Relax. I see so many guys go into an interaction with a girl and you’d think that he was about to go put in a hard day’s labor at the railroad. The first step to having fun meeting women is to relax. This girl won’t be the last girl you’ll ever see. In fact, there are probably dozens more in the immediate vicinity. So take a deep breath and don’t put so much pressure on yourself.

  • Don’t Take Yourself Seriously. You’re probably going to mess up, embarrass yourself, say something dumb, or otherwise do something that will make you feel foolish in every single outing you go on. So learn to laugh at yourself. This is one of the most important skills for having fun. Just laugh and realize that no one cares anyway; you’re not special, so just laugh it off and move on.

  • Don’t Change Your Plans For the Sake of a Girl. If your plan was to end up at the Aqua Lounge with your friends, don’t suddenly go to the club just because you met a girl. Include the girl in your plans, or find a compromise, if things are really going well. But don’t change the entire plan for your night just because of some girl. That’s chasing.

  • Do Things Because You Want To. Do you want to dance? Do you want to ride a mechanical bull? Do you want to jump around singing along to Livin’ on a Prayer? Then do that stuff because you want to, not because you’re trying to get a girl’s attention or impress her.

  • Make Interactions Interesting For You. Yes, deep dive the girl. Yes, escalate with her and keep the interaction focused on her. But, also make sure that you’re an active agent as well. Tell a story that’s important to you. Move the conversation to something you find interesting. Tell a joke that you enjoy. Just because she’s a girl doesn’t mean that she’s the only important part of the conversation. It takes two to tango. So if you want to have fun, make sure that you’re being stimulated in an interaction as well.

  • Laugh Off Rejection. Rejection is going to happen. So what? Laugh it off. Say something ridiculous like “But I thought they could make a tragic play about our love story!” Use rejection as a stimulus to keep your state up and to learn outcome independence.

It Makes It Fun for Her

One of the easiest ways to have a girl form positive associations of you in her mind is to make an interaction fun for her. And the easiest way to make an interaction fun for her is to be having fun yourself (because of mirror neurons, relational empathy and the law of state transference).

This doesn’t mean that you have to be entertaining her or putting on a comedy act, but it does mean that you should be making her smile, compelling her to be sexually engaged, and creating an atmosphere of a back and forth of masculine and feminine energy between the two of you.

One of the biggest turn offs for a girl is having to put up with a guy who is trying to impress her and is taking himself way too seriously. There is definitely truth in the old saying that “girls just want to have fun.” So make it fun for both of you.

Wrapping Up

Having fun isn’t so hard. It’ll only shorten the time it takes you to learn lessons, and it’ll make your journey that much more enjoyable.

Society will try to make you rigid and regimented. But be fluid and free. Realize that you only get one shot at this crazy show called life, so wouldn’t you want to end it with a hearty laugh, knowing that you took chances, took action, and gave it everything you’ve got?

Carpe Diem,


Colt WilliamsAbout the Author: Colt Williams

Raised in the American Midwest, Colt Williams made a name for himself in dating with a style based on soulful poetic seductions and playful dance floor antics. His style is all about inspiring girls and drawing them into one’s world. You can book phone coaching with him here, or get a copy of his guide to getting laid on Tinder, the product of months of study and experimentation by him on the medium.


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JLap's picture

Hey Colt,
I know you're pretty young, so you are probably best qualified to answer this question. I'm in high school and recently met this cute virgin. What's the best way to escalate on a girl that has no sexual experience. I want this to be special for both of us, so I want to do this right. Any thoughts?

Sam2's picture


How can you have fun with women, while also keeping an eye for satisfying your desires with her?

How can you trick your male, outcome-driven brain to take some distance from its deepest desire (i.e. sex)? Maybe the idea that "If I don't have sex with this girl, I will do have sex with another?"

Anonymous 's picture

Thanks for focusing on this. I had the same thoughts when my percentages went from bad to nonexistent. I also analyze every interaction I have with women. One thing was- I was thinking so much about process(doing the right things) that I came across as boring and chasing. I started thinking about how story telling is opposite of being analytical. If you do it right, you can hold their attention, increase their attraction, and reveal details about yourself without seeming too eager. You can be enthusiastic without using effort. Do I rehearse these stories? Absolutely! I write notes and rehearse the stories out loud to myself. The more I tell them the more fluid they get. I would suggest not starting by telling random stories. You have to probe and dovetail it into the flow of the evening. I have a loooong way to go, but by telling stories I've had the most fun with women.

MonsterzRock's picture

Great article, Colt! I've been trying to learn and apply many of the things here for months. I've yet to go on a single date for nearly a year. But it's been challenging since I work two jobs but one has cut back to one weekend a month now. Hopefully, things will change now with more times on my hands, LOL!

Anyway, I think that what you've touched on here in this article about keeping a positive attitude and keeping it fun is paramount. Sometimes I think I get information overload here at Girls Chase--all great information though. And it's easy to lose sight of the bigger picture--having fun and keeping it interesting. Thanks again....

Beginner's picture

Ok first off to explain the situation I am in:
I am 20,at college,and I see this girl 4 days per week,we are in the same group of friends but we are not actually communicative to each other like with the rest of the group,reason being i approached her year ago and she rejected me(another story and doesnt bother me now,she had boyfriend,or lied or whatever but she kindly rejected me and i accepted it and we continued our so called "friendship",she is a bit shy when meeting strangers and probably not experienced with these things outside clubs and bars,which suprises me cause she is really beautiful)...but recently when new semester started i noticed i like her again and from time to time she caught me looking at her and i gave her a note with those looks that im kinda interested again,and to mention it seems she is acting different than first time when i approached her(directly it was out of blue and bad!!)...sometimes i sense in my pheripheral view her giving fast looks at me and looking away ,but when we are in the group of friends she tends not to look at me while i speak/she speaks aka aloof towards me(lots of ppl know about our little drama year ago and some of them tend to make jokes about us often when we are close to each other,kinda making it harder for me to focus on her)...and sometimes when there is 2-3 of us she tends to ask me something showing interest about it but conversation dies ubnormally...this was quite long shitt,but i wanna know is there a possibility already that she might be interested...i hope u will answer,anyways thanks :)

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