Confessions of a Reluctant Serial Dater: An Unfiltered Tale of Love, Laughter, and Swipe-Induced Madness

Thegirlfromtheyellowapp
3 min readNov 12, 2023

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Greetings from the abyss of my dating life, where cringe-worthy encounters are not just a phase but a way of life 💃.

Picture this: an Asian twenty-something navigating the tumultuous seas of romance on Medium, because, well, oversharing is a skill, right? My mission: spill all the juicy, embarrassing details, in the hope that somewhere out there, a past version of me is desperately Googling ‘how to survive awkward dates.’

I’ve collected more dating tales than I have socks (matching or otherwise), to the point where I confidently began this saga with the grand title, ‘Love Labors: A Chronicle of 50 Dates.’

But, I won’t promise you an exact count of 50 dates just yet — I haven’t resorted to dating spreadsheets, lets just say that my love life has a multiplication addiction that rivals rabbits on a Netflix binge.

And before you picture me with a ‘date-a-day’ calendar , let me set the record straight. I’m not out here amassing romantic conquests like some Tinder warlord (or Tinder Samurai) collecting matches. I’m just a hopeless romantic (or a stone cold fox as my friends call me) caught in the whirlwind of dating apps, seeking the rare and elusive species known as the ‘great partnership.’

But before we get to anything else, let’s address the elephant in the room -dating apps. I maintain the same opinion I had before I started using them; using them is like window shopping for a soulmate — superficial, a bit judgmental, and you end up questioning your life choices. Swipe right for potential soulmate material, swipe left for “I can’t believe they chose that profile pic” regrets. Honestly, I had no expectations when I signed up either.

Yet, despite my skepticism, I’ve discovered that dating apps are the unexpected stage for a comedy-drama of epic proportions. From dazzling highs to cringe-worthy lows, each date is a mini adventure, a nugget of narrative gold that deserves its own spotlight.

To the effect that every time my closest three friends contact me, that’s the first thing they want to talk about (forget about my well-being). It’s like they’ve subscribed to the ‘Dating Chronicles’ newsletter, eagerly awaiting the latest installment of my romantic misadventures.

Sure, not every date has been a smash hit, but each person I’ve encountered has been a character in the grand theater of my love life. And let me tell you, even the ‘not-so-great’ ones have a way of leaving a lasting impression, like a bad movie you can’t help but discuss afterward.

So, here I am, determined to immortalize these tales before they fade into the abyss of my forgetful brain. Whether you’re here for a good laugh, a sympathetic cringe, or just to revel in the chaos that is modern dating, I invite you to join me on this rollercoaster ride.

So, welcome to the unfiltered, occasionally awkward, but always entertaining world of my dating escapades. Here’s to hoping it’s not exactly 50 dates, but hey, who’s counting? 😏

Here is my cringe worthy first date experience: Swipe Right, Flip Hair: My First Date Disaster.

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