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Why So Serious? How to Be More Playful on Your Next Date

He knows how to be more playful on a date

Playful people are more fun to be around, that much I’m sure we can all agree on. So, it should come as no shock that learning how to be more playful can see a massive improvement in your dating life.

In this article, we’re going to look at exactly what that means, specifically for dating. I’m going to give you some actionable tips you can start using throughout your dating that’ll help you out a lot.

These changes will be reflected in every part of your dating life. From messaging on dating apps and websites to texting and throughout your dates. When used correctly, your dates will be excited to see you again because you were so much fun to be around.

How to Be More Playful As A Man

I don’t know about you but when I hear this phrase, I immediately think of childish antics. Since running around with your arms out while you make plane sounds probably isn’t the best move on a date, let’s first change how we look at this topic.

Although children are inherently playful, that doesn’t mean that being playful is inherently childish. To oversimplify it, learning how to be more playful is about taking life less seriously and being more spontaneous. Let’s take a look at some actionable tips you can start using right now.

Mix up your routine, make “fun” part of your life

A man listening to some music while doing chores

Growing up, we’re constantly told to, well, to grow up. To stop being childish and “act like an adult”. At the time, that’s probably good advice. The thing is, when we hear it enough, we come to believe that we need to “act like an adult” every day if we’re going to be successful; if we want people to take us seriously.

Although there’s some truth in that, it’s about balance. We can’t go through life acting like a five-year-old but we don’t need to emulate a grumpy old man, either.

“Acting like an adult” is overrated in most contexts so it’s time to break up your schedule. Make time to do fun, playful things on a regular basis. Sing, dance, look for shapes in the sky, play board games, jump in puddles. It honestly doesn’t matter.

You just need to break out of this pattern of “acting like an adult” and have some fun every day. It’ll soon change your entire outlook, which kick starts a chain of positive improvements.

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Become a yes man

This one sounds silly but it’s the greatest change I ever made in my life and you should try it too. If you haven’t seen the Jim Carrey movie Yes Man, you should. In short, he starts saying “yes” to everything, whether he wants to or not.

He finds himself in situations he never would have before, meeting fun and interesting new people. Others actively want to be around him because he’s so positive and fun to be around. Of course, in the real world, we can’t literally say yes to everything, but we can take away the key message this movie gives us: If you’re not open to change, there can be no change.

At one point in my life, I was in a serious rut and life had lost its shine. I was a business owner with clients, taxes, ongoing expenses and a house. I didn’t have time for fun, this was serious business! So, the closest I’d get to having fun is saying “no” to friends and playing World of Warcraft at home by myself.

After watching this whimsical, silly movie, I decided to put the idea into practice. The next day I happened across an old high school friend while I was out for a walk. He invited me to come to a nightclub with him and some others that night — my worst nightmare at the time. I forced myself to say yes and it was a major turning point for me.

After 12 months of doing this, I had new friends, a new and active lifestyle, a gym membership and had lost about 50lbs. Life was great! I had become the fun, positive guy that people wanted to be around.

Learn to laugh at yourself

A man enjoying his work

When you can start making these types of changes and truly getting enjoyment from life, you also find your confidence growing. This is great for a few reasons.

First off, confidence is a trait everyone finds attractive. Second, it means you get comfortable laughing at yourself.

When you can take a step back and learn to do this, it changes the entire mood around situations that could have been negative. It also pushes you to do things you might not have because you would have “failed”.

My most recent example of this turned out to be another fun day with friends — tears of laughter. I’m decent on a snowboard but never tried to ski. When a friend offered to teach me, my exact response was “sure, I’m down for a day of laughing at myself”.

The old me would have refused to do that. I would have seen it not as an opportunity for playful fun but as a series of failures in front of friends. “What will they think of me when they see that I can’t do it?” (Pro tip: Nobody cares if you fail at something new).

Stop taking yourself so seriously and learn that it’s okay to laugh at yourself. If you can’t do this, then learning how to be more playful and fun will be a struggle.

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Let it go

Another important element I learned over time was to make like the Disney song and let it go. When frustrating things happen, we have two choices. We can either hang onto them and let them stew, eventually ruining our day. . . or we can shrug it off and move on.

All the playfulness in the world is ruined if you let a simple mishap derail your entire date. Another perfect example of this, a few weeks back I met up with a woman at a bar for a first date. 

Our server completely messed up the order and brought us random cocktails. Rather than getting frustrated and demanding the correct drinks, we decided to roll with it. Honestly, they were terrible but hey, nobody died.

Instead of being mad about it, this became a game of ordering each other the worst-looking things on the menu.

Yeah, it’s silly but that’s the point. There’s another word we could use for this too and it’s. . . playful. This simple, playful response to a mistake took what could have been a bad date and turned it into dinner, more drinks and ultimately, her staying the night.

Be spontaneous

Surprising his girlfriend

When I think of my most playful friends, spontaneity is the first thing that comes to mind. It’s not uncommon for them to stop on the side of the road to go do something random, just because they feel like it. Or for them to read a sign, turn to the group and say “you guys want to do it?” with an excited look.

This simple kind of playfulness is a great way to keep things from getting stale. It keeps life fun and exciting and not only is that fun to be around, but it also leads you to fun experiences.

Since we’ve normalized new experiences on a “because why not” basis, our last month alone, we’ve:

  • Been ice skating
  • Tried skiing
  • Been to a shooting range
  • Gone go-karting
  • Had a night of experimenting with themed cocktails

None of this is mind-blowing and it doesn’t have to be. The point is, it’s playful fun that keeps things interesting. By this point, we all know that if we set out to do something one night, there’s a good chance we’ll end up doing something entirely different.

When you roll this same mentality into your dating life, you’ll realize that any date can be a fun one. Meeting for coffee no longer means literally meeting for coffee then leaving, it means starting with coffee and seeing where the date ends up. Playfulness makes you that much more interesting.

Stop holding back if you want to do or say something fun

This goes hand in hand with spontaneity and will take some practice. You’ll be surprised just how many people will be on board with your ideas if you have the courage to voice them.

The next time you see something you’re interested in trying, put it out there to your friends or your date and see where it goes.

Remember, these ideas don’t have to be amazing experiences. It can be as simple as trying something you’ve never done or even doing something you know you’ll suck at. The point isn’t to give your date some incredible story to tell her friends, it’s to be fun and playful. When you can do this, you’re immediately more fun to be around.

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Mix this all together and playfulness will become your default state

The thing about learning how to be playful is that it takes some effort to form those habits, then it becomes second nature. You quickly learn that it’s okay to take risks, it’s okay to laugh at yourself and it’s okay to do things “just because”.

Once you’ve got this reassurance, it becomes second nature and essentially a (great) part of who you are. Congratulations, you’ve become that playful guy that people want to be around. This kind of playful attitude in dating will give you a more positive outlook on the whole process.

Not only that but you’ll start to notice the people around you will respond in a different way. Women will start to pay more attention to you and options will open up that you never thought possible before. Dating is meant to be fun and learning how to be more playful is a major step in getting there.

Getting your first message right is important but a great dating life begins long before that. Start working these tips into your everyday life and you’ll see for yourself how effective it is. Good luck!


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