How To Stop Seeing Dating As A Job & Embrace It As A Playful Adventure

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When did we forget that dating isn’t supposed to be a job, but a fun adventure where you can play, explore your curiosity, and create memorable experiences (even if you don’t end up with the person)?

I was recently interviewed on two dating podcasts. The famous Date/Able Podcast hosted Julie Krafchick and Yue Yosemite Xu and Sandy Weiner’s Last First Date Podcast.

We explored how play is related to dating. I got inspired to explore how dating is just another form of playing. Now, I am no expert when it comes to dating, but I do consider myself a play aficionado. I can recognize when two people are compatible enough to play, so why not delve deeper and see where my curiosity takes me?

Think of all aspects of dating: Initially reaching out, flirting, dating, relationship.

Flirting/Dating/Relationships is simply saying Yes And…

This is the main principle of improv. You put out an offer, and you see if the person is willing to build off it or just says no.

Reaching Out Through Play

Do you remember how scary it was the first time you went to the playground as a child and asked a kid if you could play with them? The anticipation was both exciting and terrifying. What if they said no? What if they said YES?!

We still have those same feelings as adults when we approach someone either in a bar, on a dating app, or via a DM.

Each time we reach out and say, “Hi, I’m _________, how are you?” It brings us back to that playground moment. That person can either play along and say Yes And…or end the play simply by ignoring you, being silent, or blatantly saying no.

What is so exciting about that initial reach out, though, is that one risk could be the one that changes your life.

All you need, as they say in the movie We Bought A Zoo, is 20 seconds of courage:

Sometimes all you need is twenty seconds of insane courage. Just literally twenty seconds of just embarrassing bravery. And I promise you, something great will come of it.” — Benjamin Mee

Benjamin Mee initially reaching out and using his 20 seconds of insane courage.

This is a possibility on any day in any interaction to meet someone that will change your life forever. You never know when or how it will present itself.

Dating Play Experiment #1: Identify a 20 Seconds of Insane Courage Moment & Act Upon It

Regardless of the outcome, simply taking the risk will open all these new possibilities that you didn’t see before.

Flirting Through Play

People are constantly playing this improv game when flirting. Good flirters make it enjoyable to play the Yes And Game and make it easy to say yes to things. It is easy to talk to certain people because you are doing a dance of building off one another, listening to each other, and not negating each other’s experience. You may even be mirroring each other at moments. A perfect example of this is from Meet Joe Black:

Have you ever been in a conversation that is going really well, and suddenly, it gets awkward? It’s because either someone stopped yes anding because all of sudden the safe place of trust you were building just got broken. SNL captures this perfectly:

The shared agreement that you had built in the play all of a sudden crumbles. Why does the blatant toxic masculine approach to flirting not work? Because no trust has been built, and that person wants something from the other person. There is no give and take. Just take.

Shia Lebouf so eloquently talks about this give and take feeling:

People, usually men, are so impatient to get a result, they ignore creating a safe space to play. That is why bad flirting becomes creepy quickly because you feel unsafe.

Dating Play Experiment #2: Practice the awareness of the flirting yes and recognize the give and take of the conversations and how you are contributing to it.

How To Play While Avoiding The ‘PLAY’-ers

So, what about the players? How do they fit into all this? How do you combat the players? Well, players have a knack for having you play their game. Entering their playground where they make up all the rules. Instead of it being an exchange, players are trying to get you to say yes and…while rarely saying yes back to you or even acknowledging your way of playing. A great example here from Crazy Stupid, Love:

It is not an equal exchange but instead of a formula that they have perfected, which is creepy. It’s about power and ego for them. They are obsessed with controlling the game. Some people appreciate being guided in such a fun game by someone confident who knows “what they are doing,” but be vigilant. If the person isn’t also willing to play in your way, that might be a red flag to flee.

Dating Play Experiment #3: Not only be aware of the players but if you feel inclined, call out the players on their BS.

Perhaps, like in Crazy Stupid, Love, there is a sensitive, sweet, insecure human being suffering under that pristine facade.

A True Play Connection

True vibing is when you both are saying Yes And to each other. It feels like magic. It’s so easy to talk to them. It almost feels like a dance that you both were meant to do together. It happens so rarely, but when it does, it can be intoxicating and leaves you with a feeling that you’ll cherish for the rest of your life. This scene is Meet Joe Black captures it so eloquently:

So, if you’d like to flirt through play, then allow your nerdy, weird, unique self to come out. If you are obsessed with something in particular like Mesopotamian folklore, the reality show 90’s Day Fiance, or baking sourdough bread, show that strange side from the get-go. Share it and see if they are willing to play in the sandbox. Even if they can’t relate to it, if they are curious to want to know more because you are so excited about it, that’s a good sign.

We always play it safe when it comes to dating by not showing our true selves, but then how can we attract the people we want then.

How can people who want to play in your way know how you play if you choose to play boring games (I.e., pretending to be normal) that you don’t even like?

Dating Play Experiment #4: Allow yourself to be seen. Please don’t do it for the other person, but do it for yourself.

The more you can practice embracing your weird, nerdy, strange, true self, the easier it’ll always be to be that way.

I partly agree with this quote below.

Now, I’m sure you have heard “you won’t find love until you love yourself first.” I believe that quote is incomplete, as I know some people who found love that didn’t love themselves first. I think you have to come to a place where finding love is a bonus, instead of your birthright. So much of the time, we don’t want to do any work but want all the rewards. We want to lose weight, but not work out. We want to feel healthy, but continue to make unhealthy choices. The same goes for love. We need to explore of what is the work we need to do in order to make ourselves open to love.

  • Can I learn to love hanging out with myself?
  • Can I celebrate my own awesomeness without needing validation from others?
  • Can I give myself tough love when I know I’m doing something that doesn’t serve me anymore?

If I get good at loving myself, I won’t need someone else to fill in the gaps that I can only fill. Also, by learning to love myself, I now know how to show more love towards others. If I practice criticizing myself, I’ll get good at doing that to others. So, I have to decide what do I really want to do.

Dating Play Experiment #5: Explore what does it mean to love yourself and consistently do this work.

Dating Through Play

I recently saw this quote: dating should be fun and having expectations make it hard to have fun. Having such high expectations can destroy the play in dating.

If during your last date the entire time you were listening to your inner critic saying the following:

Can I be with this person for the rest of my life?

What will our kids look like?

I wonder how he treats his mother?

Does he always dress like this, or is this his best outfit?

There are some ways in which he resembles my ex. Uh oh!

Wow, he is super short. I promised myself I’d never date short men.

When we are future tripping, we lose the opportunity to be in the moment…That is where play exists. I define play as any joyful act where you forget about time. You can’t do this when you are constantly thinking of the past or future.

If the date is going well, our rational mind also starts to explore foreboding joy, waiting for us to discover something wrong with that person.

We must recognize, as Albert Einstein says, “The intuitive mind is a sacred gift, and the rational mind is a faithful servant. We have created a society that honors the servant and has forgotten the gift.” We have to be careful not to lean on the rational mind to help us play, as the rational mind’s job is to keep us alive and away from danger.

I consider play the opposite of perfection. Perfection is rooted in shame, ego, and constantly looking for the “right way.” Play is built off of experimentation and curiosity.

So if you want to know if you are playing on a date, simply ask yourself, what is driving my decisions right now? Play or Perfection?

To embrace a play-oriented mindset on a date, stay curious.

Allow yourself to be present. Be vulnerable. Be open. Allow others to see you, the real you.

How do you play in a way that finds the person of your dreams?

You show them how weird, nerdy, and unique you are from the start. They either choose to play with you or not. It’s better that you do this early rather than pretend to be normal to feel accepted.

Dating Play Experiment #6: Stay present in the moment and be curious. Recognize what drives your decisions, play or perfection and choose the one that makes you feel good.

See The Date As An Adventure

“You learn more about someone in an hour of play than a year worth of conversation.” — Unknown

If that is the case, why not go all-in with play on a date, rather than, as Chris Rock says, having your representative (i.e., Your subdued, normal you) go on a date for you.

If you are ready to play on a date, suggest some adventures that embody how you love to play. This TikTok is a great example of this:

For people that are not able to watch the video, here is the premise:

On one of his first dates with his eventual girlfriend, this guy told her at the start of the date, pick a number between 1–10. She said 7. Then he asked her to pick a number between 1–100. She said .94. So they went to a thrift store, and he said, you have $7.94 to dress me however you’d like, and I get to buy your outfit with the same amount of money. Then, they went to a fancy restaurant dressed in ridiculous garb.

Now, what I love about this dating idea is it creates a playground. This idea might not speak to you in particular, but it was an opportunity for the person to show how they liked to play. If she didn’t like to play in that way, that would have been a good thing as they know they aren’t compatible.

By going on this adventure together, trust was built as he was saying I trust you and she reflected that trust back to him. They also had a shared experience of going into a place vulnerable (I.e., A Fancy restaurant in strange clothing), with the possibility of being judged by others, so they would need to lean on each other for safety.

Creating experiences on your date are ways in which to decipher if this is a person you want to go on a longer adventure with.

Now, if you have no idea how you like to play, try this experiment with your friends to remind you who you are and how you love to play:

Once you identify how you like to play, have your friend help you through a tipsy brainstorm, where you come up with all these possibly dating adventures you can try. Then try them and see what comes about.

Even if you end up not meeting the right person at first, you’ll at least have memorable, adventurous dates that you can look back on and savor.

Dating Play Experiment #7: Embrace the adventure of dating and brainstorm possible dating ideas that embody your type of play.

Playing With Your Past

“Don’t let your past dictate who you are, but let it be a lesson that strengthens the person you’ll become.”

— Louis Mandylor

I remember someone telling me that you are often in a relationship to learn a certain lesson about life. When you have learned that lesson, either the relationship ends because you have finished that part of the journey or decide to learn other lessons in life with your partner. So, we are constantly choosing to continue the adventure and see if this person is still the one.

While discussing with a friend of mine, I thought of an interesting play experiment to explore your past. Have you ever written down every person you have ever dated? It’d be interesting to write down each of your relationships and then write down what lesson you learned from each one. What did you take away from that relationship that helped dictate what was next? Were there times when you didn’t learn a lesson and ended up repeating the same mistakes? Of course, you’d only consider the relationships or dating experiences that left an impact. You might even have certain dating experiences that left a greater impact than some long-term relationships. Simply being curious and reflecting on your dating history might help you to explore what is next. It’ll also help you avoid making the same choices that do not bring you joy or fulfillment anymore.

Dating Play Experiment #8: Write down your dating history and what you learned from each relationship. Did the lessons you learned from a previous relationship dictate your next one, and if so, how?

Playing In A Relationship

People think dating ends when you are in a relationship, but I think this might be the most important time to date. We get really lazy when we have been in a relationship for a long time, and we start to only see the mundane qualities in each other. Dating is an opportunity to create new stories, new experiences to dive into, and create new tales to share.

My friend, Angie Cole, shared with me a philosophy she has with her relationship, called Open Hand. Not open marriage, but Open Hand. The idea is that you are like a bird that can land on the hand, which is the relationship at any time. Most people have a closed-hand relationship, where at some point, you just aren’t allowed to leave. With Open Hand, though, if you decide to leave the hand one day, that is completely understandable. By giving this sense of freedom, you have to decide every single day, do I want to continue to love this person? That makes the love between two individuals stronger because they realize each day they have a choice.

One of my favorite Rom-Coms where I feel captures what I believe true love is is Eternal Sunshine of The Spotless Mind. In the last scene, the two main characters are told all of the horrible things about each other and what they may end up hating about each other. Then, they have a choice to choose to love the person's flaws and all, and possibly get hurt, or leave and avoid getting heartbroken. You can see for yourself what they choose:

Embracing Beautiful Sadness

There is something beautiful about agreeing with the Love Actually Quote:

Let’s Get The Shit Kicked Out of Us by Love

Being able to show up in each relationship with radical honesty, vulnerability, and embracing your fully, weird, nerdy self, and loving the way you wanted to love should be considered a success. There is a beautiful sadness that comes with loving unconditionally, but that is what makes life worth living, as this Southpark clip so eloquently states:

Dating Play Experiment #9:

Let Yourself Get The Shit Kicked Out of You by Love

Allow yourself to get hurt and see if you can get up again. It’s a really hard process. I just did it myself, but if you are able to bounce back and be resilient, you are so much more open to love even stronger…and that’s inspiring.

Deserving, Manifesting, & Being Worthy

I recently spoke to my friend, Dr. Marcie, who put me on to this fascinating theory between deserving, manifesting, and feeling worthy when it comes to love.

The Universe Owes Me

I DESERVE…

When you feel you deserve love or at least a good date, you believe it is owed to you. I took a shower. I bought a new outfit. I got all fancy. Therefore, I better have a good date. When that doesn’t happen, you are disappointed and feel ripped off after putting in all this work…and whose fault is it? It’s my date's fault for not fulfilling my expectations.

I MANIFEST…

Some advice around love tells you to manifest what you want. I am love and/or I am loved. This date will be amazing because I am amazing. The problem with manifesting alone is there is no action. You are still waiting for something to happen to you, waiting for the universe to act, so you can get what you want. When it doesn’t happen, you then think you are a horrible manifester.

In this model, the responsibility is outside of yourself. Don’t blame yourself because you showed up and did your vision board! So, you blame the universe, or you blame the other person for not being ready.

I AM WORTHY…

When you use the term “I am worthy” of love, you are stating that you are ready to receive love. Once you believe this, you will take action to take in that love. You will put yourself out there more. You will be more vulnerable, and if nothing happens, that’s ok because you are still worthy of love.

You recognize that nothing is owed to you. You do know what you are worth, though. You are making a statement that you are ready to be loved and cherished for the amazing person that you are.

Whether that comes or not is out of your control, but you can decide if you are willing to take it in. The more we practice stating what we are worthy of, the closer we are to not only manifesting what we want and believing the universe is helping us, the more willing we are to take action to let that love finally come in and receive it.

In this perspective, it is up to me and me alone what is in my heart. Knowing I am worthy is something no one can take away from me. Being worthy will motivate me to take action. It is my actions that will bring in love, not someone else or something else — me and me alone!

Dating Play Experiment #10:

  • Write down what you are worthy of when it comes to love and see what comes out.
  • Repeat that to yourself as a mantra for a week
  • Take action based on your curiosity and see what magic unfolds

Dating Play Experiment #11:

Create Your Own Play, Fun, Joy Moments For 2021 for yourself.

If someone is lucky enough to meet you that brings you immense joy and makes you feel alive, when you feel ready, they can join you for the ride.

Dating Experiment Recap

#1: Identify a 20 Seconds of Insane Courage Moment & Act Upon It.

#2: Practice the awareness of the flirting yes and recognize the give and take of the conversations and how you are contributing to it.

#3: Not only be aware of the players but if you feel inclined, call out the players on their BS.

#4: Allow yourself to be seen. Please don’t do it for the other person, but do it for yourself.

#5: Explore what does it mean to love yourself and consistently do this work.

#6: Stay present in the moment and be curious. Recognize what drives your decisions, play or perfection and choose the one that makes you feel good.

#7: Embrace the adventure of dating and brainstorm possible dating ideas that embody your type of play.

#8: Write down your dating history and what you learned from each relationship. Did the lessons you learned from a previous relationship dictate your next one, and if so, how?

#9:Let Yourself Get The Shit Kicked Out of You by Love

#10: Write down what you are worthy of when it comes to love and see what comes out. Repeat that to yourself as a mantra for a week. Take action based on your curiosity and see what magic unfolds.

#11: Create Your Own Play, Fun, Joy Moments For 2021 for yourself.

CONCLUSION

I don’t know if I’ll ever find the love of my life. I hope you find yours. Regardless though, we owe it to ourselves to find the fun and the play in the process of dating. To see it as an adventure, a luxury that many others do not have. To have self-compassion, grace, and care to see ourselves as a whole person regardless of our relationship status.

Because you have one life.

Determine how you want to connect and how you want to love.

Because all you have control over is you and how you want to show up in the world right now.

So, enjoy the ride.

Workplace Positive Psychology Play Whisperer / Helping Fortune 500 Companies Build Psychologically Safe Workspaces Through Positive Psychology & Play