The Dating Game: Where Authenticity Wears a Mask

Why not take off this mask and embrace authenticity? After all, we are all looking for that special person with whom we’ll share a lifetime.

Serene Wanderlust
Modern Women
5 min readJul 25, 2023

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Photo by photo nic on Unsplash

The Masquerade of Online Dating

Picture this: a cozy night in, swiping through profiles, and boom! A match appears, and you can’t help but wonder why the universe brought you together. But hold your horses! Let’s unravel this online masquerade. People out there are diving into the dating pool for all sorts of reasons: societal pressure, fear of aging alone, or just wanting to follow the herd and be in a relationship.

The Direct Question Conundrum

But wait, there’s more! The dating tango comes with unspoken rules, like avoiding direct questions on the first date. Seriously, is asking about kids really a red flag? In my experience, it’s more like a time-saver! Take my ex, for example. Five years into the relationship, he “didn’t want kids” but assumed he’d magically change his mind. Surprise! He didn’t. Lesson learned, folks.

The “Me vs. Perfect Partner” Dilemma

Ah, the art of pretending to be the perfect partner. We all do it, don’t we? Trying to impress each other with grand theatrics, hoping they’ll fall madly in love with this polished version of ourselves. But once you move in together, brace yourself for the truth — no more acting. Let the real games begin!

Getting Real: The Game-Changing Questions

Now, let’s steer this ride in a different direction. If you’re looking for a future partner, why not skip the charades and dive into the nitty-gritty with some bold questions? What are their priorities in life? Their burning desires and life missions? Do they see themselves with kids in the future? What’s their definition of greatness? Talk about cutting to the chase!

Fear of the Deep Questions

Alright, confession time. I used to be afraid of asking these soul-baring questions. Fear of looking “thirsty” or desperate kept me from taking the plunge. But you know what? That fear became my compass. If a potential partner can’t handle a little depth, it’s their loss! Time to dodge that bullet and move on to someone who’s more than willing to explore the depths of life with me.

The “Go with the Flow” Fiasco

Ah, the allure of going with the flow — it sucked me in too. I spent five years in a relationship, flowing downstream with no concrete vision or direction. We were simply existing together, and as time passed, I realized our paths diverged. Yet, I stayed, perhaps out of comfort or fear of starting anew.

Embracing Self-Love and Learning

It was time for a wake-up call! As I found myself single once again, I embarked on a journey of self-discovery. Love began within — embracing my priorities, my purpose, and the kind of relationship I craved. The answers to those deep questions suddenly became clear, and I felt empowered.

Communication: The Key to Authentic Connections

To navigate the treacherous dating waters, I learned that communication is queen. Embracing those deep conversations, even if they felt overwhelming, became a catalyst for understanding myself and what I truly sought in a partner. It’s refreshing to dive beneath the surface and find the pearls of authenticity.

The Podcast Revelation

And let’s face it — dating can be as confusing as a Rubik’s Cube. You twist and turn, hoping to find the perfect match, but just when you think you’re close, the colors clash, and you’re back to square one. But don’t worry, my fellow daters, we’ll crack this code eventually! Until then, happy dating — and may the sarcasm be with you!

And speaking of soul-baring questions, I stumbled upon this gem of a podcast, “The School of Greatness” by Lewis Howes, and it had a real “aha!” moment for me. His guest, Martha Higareda (his actual girlfriend), spilled the tea on the questions we should be asking before committing to a relationship. Brace yourselves for some serious gems:

  • What’s your priorities in life? (Besides swiping on dating apps, of course!)
  • What is your mission? What is your purpose? (And here I was, thinking mine was just to survive Mondays!)
  • What is your burning desire? The thing that makes you happy every time you wake up (Is it Netflix or finding “the one”?)
  • Do you see yourself married? Do you see yourself with kids in the future? (Are we swiping right for a wedding or just a weekend brunch?)
  • What’s your definition of greatness? (Because we all want greatness, right? But what does it mean?)
  • What are your sexual expectations? (Oh, don’t blush! It’s a legitimate question!)
  • What do you expect from a partner? (Sorry, no time for guessing games here.)
  • Can you talk to me about a childhood trauma? (Okay, maybe not the sexiest topic, but it’s a game-changer!)
  • What is your Bucket list? (Skydiving together, anyone?)
  • What would be your dream house? (Do you prefer a cozy love nest or a bachelor pad?)

I was amazed! But let’s be real, I was also a tad afraid to ask these questions. What if the guy thinks I’m conducting a presidential interview or some undercover investigation? But then I realized — if he can’t handle the heat, he better get out of my kitchen. It’s not about being desperate; it’s about saving precious time.

I’m Tired of Being Lost

Maybe you’ve been there too — going with the flow, hoping everything will magically fall into place. But trust me, as tempting as it may seem, it’s like swimming against the current. The deeper you get, the harder it is to change direction. I finally learned that going with the flow without a destination in mind is a recipe for relationship disaster.

Let’s Make Waves with Authenticity

Now, I’m on a journey of self-love, embracing the power of knowing what I want and need. You see, my priorities are no longer a mystery wrapped in an enigma — they’re clear as day. And guess what? I’m not afraid to communicate them! Gasp Yes, it’s shocking, I know.

So, fellow adventurers, let’s not get lost in the fog of dating masquerades. Embrace your priorities, ask those soulful questions, and find someone who’s ready to embrace the depths of love and life with you. And who knows, maybe one day we’ll meet a partner on the same wavelength, and together, we’ll navigate the rollercoaster of love, laughter, and “What on Earth?!” moments.

And let’s face it — dating is as mysterious as the Bermuda Triangle. One minute you think you’ve found the treasure, and the next, you’re left in a dating abyss, wondering where you went wrong. But fear not, my fellow daters, for with each experience, we’re one step closer to finding the real deal. So keep asking those questions, swiping right with a wink, and may the sarcasm be with you!

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Serene Wanderlust
Modern Women

Nomadic Product Designer, aspiring writer, I write about life, love and my nomadic life.