How to be More Playful and Fun

“How can I relax, let go, and have more fun instead of being serious all the time?”

Picture yourself interacting with a group of people:

  • Are you laid-back, laughing and talking with everyone, and following the natural lighthearted flow of conversation?
  • Or, are you serious, quiet, keeping to yourself, and feeling lonely or left out?

If you feel the latter, today’s post is made with love just for you.

Many introverted men want to connect on a deeper level, which can be hard when the vibe around them is one of laughter and jokes.

How can you be more playful and fun to form lasting connections when you feel unable to relate?

In this post, we’ll talk about how you, as a thoughtful introverted man, can…

  • learn the skill of being playful in conversations,
  • take note of ways you can increase playfulness in your own mindset, and
  • practice these conversational skills over the long-term to cultivate your light and fun side (you do indeed have one!).

Using the tips we discuss here, you will be able to build your conversational skills in a lighthearted way. With time, you will understand how to relax, unwind, and be more playful with others.


Why is it important to know how to be more playful in social situations?

When you’re naturally deep and thoughtful, it can be tempting to want others to meet you on your level. If diving into the depths is your native language for connecting with others, it can be hard to understand that not everyone works that way.

And when you only contribute heavy and meaningful topics to the conversation, others may start seeing you as too serious or one-dimensional.

The key is to gently step outside your comfort zone and meet others on their levels (we’ll show you how!). Sometimes that means relaxing into a lighthearted mindset and going with the flow.

After all, playfulness is an important part of relationships.

If you can master this skill, you can avoid coming off as overly intense or out of touch. Instead, you will be able to showcase the fun, happy side of yourself that attracts other people to you!

As a bonus, you will be able to genuinely have fun and enjoy social situations more easily.

Win, win!

Conversational skills are the backbone of social interaction. If you find yourself wanting to make more real, lasting connections, download this free ebook. You’ll find tons of helpful tips for boosting your confidence, leveling up your dating mindset, and improving your sense of self across every aspect of your life!

Now, dive in and discover how to be more playful!


First, understand that you can learn to be more playful.

Like most other conversational skills, playfulness is an aspect of yourself that you can develop.

All it takes is time and effort.

If you look at your life and realize that your inherent seriousness and depth is an aspect of your personality that you have given a lot of intention to, you can understand how to put more intention on the less-developed aspects of your personality.

Though you may currently define yourself as “the serious one” in your social group, you can change that if you choose to!

Making long-lasting personal change begins with acknowledging that you want to change something, and then putting in the effort to do so.

Refreshingly, you can hold on to the good parts of your personal depth and intensity while putting high-strung, worried, or tense facets of yourself in their place.

When you make it a priority to learn how to relax, kick back, and genuinely have fun… it will happen, just like anything else you set your mind to accomplish!


And, here’s how to do it.

Knowing how to play is important, as play offers great ways to relate to those you’re speaking with and relax during conversations.

While each step along the path of learning to be more playful is large enough to be the focus of their own separate articles, the overarching ideas can be summed up in just a few key points.


1. Notice when things make you feel playful or when you laugh at something because it’s funny and lighthearted.

Even if you aren’t yet sure how to produce this response in other people, you instinctively know when something strikes your own funny side.

And, chances are, if you find something funny, others do too!

So make a note when something tickles your lighter side, and file those mental notes away for future reference.

Noticing these things is a matter of focus, like what happens once you’ve done some research on a car make and model, for example. By having your attention on it, you start to see it everywhere.

Keep your eye out for things like these:

  • Jokes, puns, or plays-on-words
  • Comedic timing
  • Entertaining anecdotes that hold your attention
  • Funny or strange stories you think might interest others


2. Make an attempt to hang around people who make you feel this way.

Humor and playfulness are very rarely as enjoyable when you’re on your own as they are when you can share them with others who are on the same wavelength.

If you have a certain set of friends who frequently share a great laugh, make an effort to spend more time with that group!

As for great play ideas with a group, you can all spend time playing board games, go bowling, or even show off your problem solving skills by trying an escape room!

Not only does laughter bring you closer, which is more evidence that it’s possible (and fun!) to connect on the lighter end of the spectrum, it also gives you ample opportunities to make more mental notes of things that make you feel playful and fun.

Over time, you will be able to pick up on the things these people do and say and incorporate those techniques into your own conversational style.

This is not fake at all! We are social creatures, and none of us comes out of the womb knowing how to communicate. It’s learned. So why not keep actively learning?


3. Keep your conversational contributions light at first, without resorting to mindless small talk.

To accomplish this, you can use some of the techniques you spotted others using in the previous steps.

Try your hand at telling a joke or sharing something hilarious and strange that happened to you the other day. Gauge the reactions you get from others. Use that feedback to keep developing your personal humor style for the future.

Another option is to mention a fun aspect of someone in the group. Try to keep it positive, rather than teasing. Even if your friends rib each other with good-natured insults, it can be hard to walk that line carefully until you’ve had more practice. And it’s not necessary!

When you can genuinely reflect positivity on people around you, it helps them to see themselves and others (including you!) in the same positive light!


4. Practice and give yourself time.

As with every skill, practice and openness along the way are key!

To practice keeping conversation light, you can casually introduce a topic and see if your conversation partner seems interested. If so, dive deeper into the topic!

This is also a great way to gauge whether you should elaborate more on that funny story about yourself that you touched on earlier!

It can take a few months of hanging around lighthearted, fun people before you start to understand the kinds of topics and stories that fit well into relaxed conversations.

Beyond that, it will likely take even more time before you have comfortably integrated the conversational techniques that appeal to you into your own unique style.

Don’t expect to be a 24/7 standup comedian overnight! Plus, there’s no need to be.

Meaningful results happen naturally as you allow a more playful, relaxed, and fun side to take root in your life.

There may not be a singular moment you can point to and say, “I got it!” But someday soon, you’ll be telling a funny story about yourself that you know will get a good laugh, and you’ll realize that you have come a long way.

Enjoy! Those little payoffs are so fun as you are learning how to be more playful.


Conclusion on how to be more playful

Group of Friends - Be More PlayfulNow that you understand the steps toward developing the lighthearted side of your personality, you can get to work making this a reality!

For now, let’s recap what we went over today:

  • Deciding to embrace your fun, playful side and ease up on some of your signature seriousness,
  • Making a note of the things that others say that make you laugh or feel you are having fun,
  • Using those same strategies in your own conversations, and
  • Continuing to learn and practice your skills over the long term.

If you have other areas you want to improve in addition to your conversational skills, don’t forget to download our free ebook, “Why PUA Doesn’t Work for Introverts & What Works Instead” for awesome, actionable exercises on bringing out your unique best self!

For even more in-depth help on becoming the benevolent badass we all know you can be here at Introverted Alpha, consider our 1:1 Launch Your Dating Life program for personalized, customized advice! Talk with us in a private phone call (apply here), and together we can see if the program is right for you.

Picture of Kelly from IA
Kelly from IA
Kelly is resident writer here at Introverted Alpha, which is known as the premier dating coaching company for introverted men; featured by Forbes, Business Insider, Cosmo, and more. Pick up your free copy of our 22-page ebook inside the blue box just below.

Attracting An Amazing Girlfriend Starts with Finding Your Own Vibe.

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Attracting An Amazing Girlfriend Starts With Finding Your Own Vibe.

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--> Why the “pickup artist” approach will never work for introverts and what works instead

--> How to attract women naturally being your best self

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